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Sam J
This is an iHeart podcast. Guaranteed Human.
Chad Millman
Everybody knows Shaq, but off camera, he's just a regular guy.
Shaquille O'Neal
People never believe me when I say I'm just like them. I take out the trash, do dishes, and I struggle with moderate obstructive sleep apnea, or osa. And a lot of adults with obesity also struggle with moderate to severe osa. You know, those scary breathing interruptions during sleep, the loud snoring, choking, and daytime fatigue. I knew I had to talk to my doctor. Don't sleep on the symptoms. Learn more@don'tsleeponosa.com this information is provided by
Chad Millman
Lilly, a medicine company.
Superhuman Podcast Host
Imagine an Olympics where doping is not only legal, but encouraged. It's the enhanced games. Some call it grotesque. Others say it's unleashing human potential. Either way, the podcast Superhuman documented it all, embedded in the games and with the athletes for a full year.
Mike Conti
Within probably 10 days, I'd put on £10. I was having trouble stopping the muscle growth.
Superhuman Podcast Host
Listen to Superhuman on the iHeartRadio app, Apple Podcasts, or wherever you get your
Sam J
podcasts on the Look Back at it podcast from 1979.
Clifford Taylor IV
That was a big moment for me. 84 was big to me.
Sam J
I'm Sam J.
Alex English
And I'm Alex English.
Sam J
Each episode we pick a year, unpack what went down, and try to make sense of how we survived it with our friends, fellow comedians and favorite authors like Mark Lamont hill. On the 80s, the 84 was a wild.
Mike Conti
I mean, it was a wild year.
Clifford Taylor IV
I don't think there's a more important year for black people.
Alex English
Listen to look back it on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.
Clifford Taylor IV
A win is a win. A win is a win. I don't care what y' all say. Yep, that's me, Clifford Taylor iv. You might have seen the skits, my basketball and college football journey, or my career in sports media. Well, now I'm bringing all of that excitement to my brand new podcast, the Clifford Show. This is a place for raw, unfiltered conversations with athletes, creators, and voices that not only deserve to be heard, but but celebrated. So let's get to it. Listen to the Clifford show on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. And for more behind the scenes, follow at Clifford and at TikTok Podcast Network on TikTok.
Chad Millman
Welcome to Sharper Square, presented by Hard Rock Bet. We are part of the Volume Podcast Network. This is the show that makes the squares sharper and makes the wise Guys, pay attention. I am Chad Millman. I am joined as always by my co host, Mike, BFF Mike and Patrick the Mic and Padre professional better Simon Hunter. Hello, Simon.
Simon Hunter
Chad. How we doing, brother?
Chad Millman
I think our viewers can see already that we've got our very special guest lined up and ready to go. Because it is the weekend of the Kentucky Derby, gambling preeminent right of spring is almost here. The Run for the Roses, the most exciting two minutes. In sports, the 152nd running of the Kentucky Derby. As we do every year, we're joined by a very special guest who talk all things betting for Derby Day. A man who learned to read the Daily Racing form before he could read a book. I don't think there's a difference. While safely inside his father's bar not too far from here in New Haven, Connecticut. Welcome back to the show, handicapper extraordinaire, Ithaca football legend, thoroughbred owner Mike Conti.
Mike Conti
Gentlemen, great to see you. Thank you so much.
Chad Millman
Did we cover it all?
Mike Conti
Yeah. Too much, too much, too much.
Chad Millman
Are you feeling full of puffery now?
Mike Conti
Feeling like there's even more pressure than there was before?
Chad Millman
Well, dude, listen, like I mentioned, thoroughbred owner in the intro there, and you have a horse named Miss Call, won a race at Keeneland in Lexington, Kentucky, where Simon and Matt Mitchell and I had done an event, I think, for Breeders Cup a couple years ago. You were there when Ms. Call won. I mean, Keeneland's beautiful. Just an outstanding place to spend a day. Whether you know anything about horse racing or not, if you're owning it, give us every detail, tell us what it's like. Tell us what happens. The horse goes off, what it's like in the winter circle. All of it.
Mike Conti
Yeah, it was. So I've been fortunate enough to own bits and pieces of horses, you know, 5% here, 10% there, 30% here. Whatever it may be for the last, like, decade now, and I've been lucky enough to have a couple that have seen the winner circle. This was the first time that I got to experience it live. And the experience, like you want to talk about, like a feeling of euphoria and just something that it's hard to describe. It was that, you know, she comes into the paddock and you're looking at her and you're looking at the competition, and you're like, wow, she looks really good in the paddock. And sometimes, you know, the way that they look in the paddock does not translate to the racetrack. And, you know, she goes out. It was a sloppy track. She had been off For a couple of months. So there were some question marks around her. I was with some friends, and going into the far turn, I looked at one of my buddies. I was like, I don't like her position. I was like, I don't know if we have any shot. And our jockey, Brian Hernandez, did an amazing job. Moves her just to the outside, takes off, and she won by six or seven lengths in the end. So it was one of those moments where, for those that have seen the movie Secretariat, the trainer is yelling at Ronnie Turcotte in the movie, Ronnie, don't fall off. Going for the wire in the Belmont. And that's kind of how I felt because we had such a big lead. I was like, brian, just hang on to her. And then, you know, the whole experience was. Was truly like. I felt like it was a once in a lifetime type of experience. And again, being there live, there was something different about it. And I. It. It changed my perspective on horse ownership and gave me even more respect for some of these larger owners who have horses that are running sometimes on a weekly basis because they have such, you know, large groups of horses. But what it's like to get that feeling, and it's an addicting feeling. I want that feeling again.
Chad Millman
What. What does it mean when a horse looks good in the paddock? How does it. How does it different race to race?
Mike Conti
You know, it has to do with, like, their physical appearance, right? So first and foremost, you know, like, are they on the muscle? Is what we say. And so, like, how fit do they actually look? Is their coat shining? Like, you can tell a lot from a horse by their coat, by their muscle tone. But also you're looking for, how are they moving, just walking around in the paddock? Are their ears pricked? There's a lot to be said in terms of just, like, with humans, the body language and the confidence of the horse. Right. I mean, horses are mammals as well. She's looking around in the paddock at her competition and trying to kind of size up her competition. And she was, as they say, on her toes, and she had her ears pricked. So all of those things on the muscle, ears pricked on her toes. You're starting to feel more and more confident as an owner of, like, okay, now we got to work out a trip.
Chad Millman
What were her odds when she went off?
Mike Conti
She went off at 5 to 2. So, I mean, she was the morning line favorite in the race. She actually didn't go off as the favorite in the race, which was interesting. What was really fun about this is the horse that went off as the favorite is a good friend of mine. And he was in. We were all watching the race together and his horse finished second. So he came up to me and gave me a big hug after, and he's like, if we were going to lose to anybody want to lose to you guys? And the funny part is he's a dear friend of my mother's. And we were laughing after the race. We're like, how did we not bet the exacta with our two horses? And we didn't. But we were laughing about it after, and it was a really cool experience. Late run, Frosty Mojito tried to take third, but the leader, missed call has passed the 16th pole for Brian Hernandez Jr. Missed call is the winner. Missed Call to take it. NZ Hawley across the line in second, Frosty Mojito third. And then Alta Avenue had to come to the far outside and came down the center of the track for fourth.
Chad Millman
Oh, that's cool. It was a very sloppy track.
Mike Conti
It was a very sloppy track.
Chad Millman
All right, so we can't jump to the.
Simon Hunter
The derby yet, Chad. I got one pressing issue. I gotta talk to Mike.
Chad Millman
Let's hear it.
Simon Hunter
So I don't try to give up too much because I always can get a little bit of trouble. So I don't know what I can say here, but I have a syndicate I work for. We had always had one guy for horse racing, and if. If he was lucky, he would have one person underneath him doing work for him. He is now up to six, and Mike probably knows why. There is a boom right now, Chad, a money boom in the horse racing world because of AI and my group has been ahead of it. I know it's becoming a little bit more mainstream now. I think the books, the tracks are starting to figure out in the general public and it should be known to people. If you are betting into this race, you can get away with it here. But if you're just going to your local races right now, you're an extreme disadvantage to people like me right now. I just want to be a board about it. It's. There's a whole thing going on that I think people don't understand right now in horse racing. Huge advantages like never before. Playing the numbers, playing the math. And I would love to hear Mike's take on that. As someone that's living in the industry that have you seen this big change happen? I'm sure you've read the stories about it. What's going on here with your mindset heading to the Derby.
Mike Conti
Yeah. You know, it's, it's funny that you guys bring this up and I will, I will try to toe the line as best I can here. I mean, as a, as someone who grew up betting the horses and you know it, I will say that, you know, some of what Simon's talking about has taken me away from the game other than bigger days. Because on bigger days, yes, you can still feel the impacts of some of these groups that Simon's talking about, but you can't feel them as much as you do on your average Saturday. And I'll give a great example. I've been fortunate to have some decent scores at not massive ticket prices. I hit a pick five at San Anita a couple years ago, I think was $150, $4 pick five that paid like 12 grand. And when Arlington racetrack rip was still open, I hit a pick five the day after the Arlington Million because there was a pick five carryover. Same thing. I think it was like $32 ticket or $144 ticket that paid like 10 or $12,000. And no crazy like long shots. That being said now with what Simon's talking about, I mean, just the day after missed calls, race was the Bluegrass Stakes, which is a Kentucky Derby prep race at Keeneland. And the pick five sequence that ended with the Bluegrass, there was a horse in there that won. I think the horse was like, I want to say the horse paid like $47. So 22 to 1, 23 to 1. So you would expect a pretty good size pick five payout. And I believe the payout that ended that pick five in the Bluegrass was only a couple thousand dollars. And when you have a horse that's paying 40 bucks in the sequence, no matter what else you had, I think you had two other favorites in that sequence. It's changed the game for the average better. And so you've got to find ways of like, okay, where are your advantages and understanding what pools are these groups allowed to bet into? What pools are they not allowed to bet into? And really getting an understanding for that. I mean, if you just go on Twitter and start following some people in horse racing, you will see these people that are talking about this because a horse enters the gate at six to one and because horse racing is paramutual wagering, you know, it's all about the live bets and odds are constantly changing. Horse goes into the gate at 6 to 1 by the time they open the gates in the quarter pole because all the money was still coming in, not after the race started. But they're calculating it. That horse is off odds might be half of that at three to one. And so as a better, if I'm expecting six to one and the horse crosses the wire and I'm like, wait, I only got 3 to 1 on the payout, like, what's the difference here? It's because a lot of that, I think that they're, you know, as an average better and as a. As a horse player and a horse lover, I think that we've got to have some better rules and regulations around this. One of the challenges in horse racing is that there's not one centralized body for everything to do with horse racing. Every track is different, every state is different. There is no centralized governing body, and we really need that. In my opinion. I could rant on this all day, but I know we're here for the Derby.
Chad Millman
Well, listen, but it's really interesting and we'll get to the Derby in a second. There was just a big story about AI and the impact it's having on horse racing and horse betting. Sometime this week. I can't remember where I read it. I apologize to whoever. Whatever outlet wrote it.
Simon Hunter
Yahoo.
Chad Millman
It was Yahoo. Okay. And to Mike's point, just for people who don't understand, paramitual means that you are betting into a pool. And so if, unlike betting on the NFL, if you bet the Seahawks at minus four and a half, super bowl and the line moves to five and a half or it moves to three and a half, your bet is locked in at four and a half. In horse racing, if you bet on a horse at six to one, that line is going to move. More money comes in. There's no getting the best of the number. And so your bet pays out at whatever the total pool of odds of money came in and move that number to when the horse race starts. So with AI they've been able to cut the amount of time when they can make their final bet basically into milliseconds. And so flood of money is coming in on these horses. And look, horse racing, you know, people don't know this in the United States. Horse racing after soccer is probably the second biggest betting event around the world. And if you talk to people in Europe and Asia, those are honestly the biggest betters in the world. They dwarf. They. They dwarf what Billy Walters used to do. They are betting billions and billions of dollars on horse racing. There have been so many stories about them. It's fascinating. Simon. I'm so glad you brought it up, Mike. Like, does it sour the experience for Someone like you who's got a horse and likes to bet and might not be doing it at the same level as sort of the professionals are.
Mike Conti
Yeah, you know, I think it, it's interesting, I think when, when computer assisted wagering is what we're talking about. Caw and when the caw money started. And Simon, you can correct me here if I'm off, but I feel like it started within the last, it's become prevalent, I would say in the last three years. I would say you started hearing about it maybe about 5ish years ago or so. I don't really remember a ton of it or hearing as much of it pre Covid. I'm sure it existed, but not to this extent. And the interesting thing is, right there's a takeout. And so that's the other thing I think that people need to understand when they're making these arguments for or against the computer assisted wagering is that the tracks, there's a takeout on every bet and the bet type differs the percentage of the takeout. So let's give a really easy example here. The wind pool for the Kentucky Derby, it's always right around 20% for a wind pool is what the takeout is. So if there's $5 million wagered into the wind pool on the Kentucky Derby, Churchill downs is taking $1 million that they take the 4 million is what is then getting paid out to betters. And so from a track perspective, and this goes back to the whole like no centralized governing body in horse racing from a track perspective, not only do they want, but to an extent they need these computer assisted wagering because of how much money they're putting into the pools. In comparison to the average better or the public, the computer assisted wagering is exponentially, I would say, more money than what the general public is betting into any given pool. And so the tracks like want and somewhat need this money. But from your average horse player or even some of these professional handicappers, it's become very challenging and off putting to find where there's money to be made in some of these bets.
Chad Millman
You know, it's, it's not that dissimilar from prediction markets because a lot of the biggest market makers on prediction markets, the group like Susquehanna, you know, the international trading firm that is the, one of the biggest market makers in the world. And for those who don't know, a market maker is basically just providing liquidity into an exchange. They could do it. The New York Stock Exchange, they could do it at any exchange. Susquehanna, which does it, in all the places, is now one of the biggest providers on prediction markets, especially calce. They're all using automated programs to change the pricing and to their benefit, which is, I'm not saying that in a negative way, but it's not an individual trader sitting at a desk looking at the price. It's a program that is identifying the price that's available and with computer assistance, it's changing the price or offering a new price when there are quotes and things like that or bids and things like that. Fascinating. Mitchell. We got to do a whole series. I think we got like a five week series on this. But Mike, as we record this, it's Wednesday, it's Whisper Wednesday at the Kentucky Derby. So, you know, in traditional gambling parlance, that's when like everyone in the paddocks starts to whisper about the horses that look good and whose ears are pricked and you know, on the muscle and things like. What are you hearing right now?
Mike Conti
Yeah, I mean, you know, if you look at. Even if you. From what you hear from workouts. Right. I think there's an interesting one in Dannen Bourbon, who's a Japanese horse. You know, the question is, is that they run the opposite way over in Japan. But ever since he's taken to this Churchill dirt, he's looked just as good. I think that's an interesting horse for sure. The Puma, who is number nine, is a horse that's taking a ton of money in, in the early win pools and I think there were a lot of people that really high on this horse. Just this morning, again, we're recording on Wednesday, just This morning, number 13, silent tactic, has scratched out of the race. And so now number 21, Great White, draws into the race. I don't know as though that that's really going to change much. And then the other horse that I've been hearing really good things about in the mornings is number 15, emerging market. So, you know, you've got some interesting horses that you're hearing some different things about. Obviously we had a scratch as of this morning. So now we've got, you know, everybody inside of, or I should say everybody outside of the 13 pole is now moving down, you know, one step closer inside and you're getting number 21, great white, drawn into the field.
Chad Millman
How much does pole positioning matter? Because the Derby is not your standard race. It's got more horses, the drama is bigger. How does all of that impact the race itself?
Mike Conti
Yeah, I think, look, the first thing for people to understand and know is that horses can only run in the Kentucky Derby one time in their life. This is only a race for three year old horses. Now another misconception is people think, oh, it's three year old males. It's not which are colts. It can be the females. The Phillies can run in the Kentucky Derby. They typically don't. They have their own race just for Phillies, three year old Phillies, which is on Friday called the Kentucky Oaks. But so the Derby is a once in a lifetime opportunity for these horses, for the connections, the owners, etc. It is for the vast majority of these horses. It is the largest field that they will ever run against a 20 horse field. The average field size in North America these days I think is like 6.8 horses or something like that. So you're talking about an average field size that is three or the average field size is three times less than what this field is being 20 horses, all of these. None of these horses have run this distance before. So this will be the longest distance at a mile and a quarter that any of them will have run. And because of the 20 horses in the starting gate, the starting gate is a special made gate and the starting gate is actually more narrow than the normal starting gate that these horses are in. So they're even more confined than they already were in the starting gate. And because there's 20 horses, they're going to be in that starting gate for longer than they ever have. And then you've got, you know, 150,000 or so people that are screaming at the top of their lungs when that gate opens. And you got to remember these are animals that react to sights and sounds and everything else. And so you know, that initial burst of sound when those gates open and everybody's going crazy. I mean, these horses have never experienced anything like that before.
Chad Millman
Wall of sound.
Simon Hunter
Exactly. So just looking at the top five, I would love to go through with the horses up top here and just, you know, get us your best view on these guys that are odds unfavored right now.
Mike Conti
Yeah. So, you know, in terms of the top five horses, we're talking about number one, Renegade. You were talking about number six, Commandment. You were talking about number 18, Further Ado. You are talking about number 12, Chief Wallaby. And you were talking about number nine, the Puma. So those are the top five from a morning Line odds perspective. As we just mentioned, odds have already started to move around and change. There's about $200,000 that's already wagered into the wind pool, which has changed these odds some. But let's just start. We'll just go in numerical order here. So number one, Renegade. This is a horse that is owned by Mike Rapoli. You may know Mike Ropoli from many walks of life, from vitamin water to body armor. Obviously Noble. He's very influential in St. John's basketball, being a huge donor there. So he's all over. I think he's an amazing owner for the sport of horse racing. I think there are some people that love him, some people that hate him. He's not won the Derby. The interesting thing with Rapoli is he had a horse a couple of years ago, Forte, that was scratched the morning of the Derby and Forte was the morning line favorite in the Derby. It was massive controversy. So it's great to see Rapoli get back into the Derby with Renegade. From the horse himself, his perspective. So he won the Arkansas Derby, which has proven to be a key prep race for the Kentucky Derby. His running style is he's a closer, so the one hole not as big of a deal. The biggest challenge for him is he's going to have to work out a trip. We'll talk about pace in a minute. I think there's plenty of pace in this race, but when you're talking about a deep closer in a 20 horse field, you got to work out a trip and that's going to be the biggest thing for Renegade. Moving on to number six, Commandment. You know, I think the Florida Derby winner. The Florida Derby in recent years has proven to be one of, if not the most important prep races for the Kentucky Derby and Commandment really hasn't done much wrong in his career. He's won four of his five lifetime starts. He's run back to back. Buyer speed figures over 100. He's got more of a stalking type, so shouldn't be quite as far back as Renegade, but we'll still be coming from a little bit off the pace there. The interesting thing is is that the prior two jockeys on Commandment, Flavian Pratt, rode him in the Florida Derby and then Irad Ortiz rode him in the Fountain of Youth. You could argue that those are the two best jockeys in North America and neither one of them are riding Commandment in this spot. He's getting a new jockey in Luis Saez, who's also a top jockey in North America. But it's always interesting to me when you have these jockeys who choose were thinking that they chose to ride other horses, which is always interesting to me. Brad Cox is a top trainer and I think it should be noted that Commandment has a win over Churchill back in November. He broke his maiden at Churchill. Then we go to number nine, the Puma. This is a horse who kind of took a little bit by storm in the Tampa Bay Derby back in March. He beat heavily favored Further Ado, who we'll talk about in a little bit in that Tampa Bay Derby, and then was a nose behind Commandment. He got the jump on Commandment in the Florida Derby, and Commandment was able to come down the outside. It was a photo. They were noses apart. So I think this is a horse that's got a ton of upside. There's something about the Puma that kind of reminds me a little bit of Mage from a few years ago in the Kentucky Derby and also has the same trainer that Mage had. So just to be noted there, moving a little bit further to the outside, you've got number 12, Chief Wallaby. This is a horse that I think is going to be a little bit closer. Should be a stalking type. This is only his fourth lifetime start. Also ran in that Florida Derby. He had a little bit more traffic trouble in that Florida Derby. He had to wait a little bit longer coming out of the far turn to get out. When he did, he made a run, but was only able to close in and finish a half a length behind Commandment and the Puma. Interesting to note here, the connections here. Trainer, jockey, combination. Trainer is Bill Mott, jockey is Junior Alvarado. Those are the two who won the Kentucky Derby last year with Sovereignty. So another interesting one to look at. And then finally, Further Ado. This is a horse who absolutely freaked last time out at Keeneland in the Bluegrass. The Bluegrass has not been as fruitful of a prep race as the Arkansas Derby or as the Florida Derby has been. That being said, Further Ado owns the highest buyer speed. Figure last time out at 106, and he won that race by 11 lengths. Now, I don't know as though that he faced any horses that were all that great. No disrespect either way. Winning by 11 is winning by 11. So, you know, I don't think there's a ton that separate these top five. And, you know, I also think it's really cool because this year I don't think that we have this like, hey, this is the horse that's supposed to win the Derby. This is the clear cut favorite. Whether odds or not, I think you've got these five that are all really interesting.
Chad Millman
All right, let's do a quick break from Hard Rock. We'll come right back. Today's show is brought to you by our presenting sponsor, Hard Rock bet, the official sportsbook partner of the Orlando Magic. And speaking of the Magic, they're back in the NBA playoffs, where the lights are brighter, the pressure is higher, and every possession can change a series. And on Hard Rock Bet, every night is your shot to score a major bucket with win or go home energy on the hardwood. Same game parlays are a great way to get in on the excitement, and Hard Rock Bet gives you tons of ways to stack your picks into SGPs built for the playoffs. And if you're ever late to tip off, don't worry, Hard Rock Bet lets you live bet all game long. Try your first bet on Hard Rock Bet today and you can score $150 in bonus bets. If you win, just place a $5 bet and if it hits, you get not only your winnings but also an extra $150 in bonus bets. And while Hard Rock Bet is Florida's only legal sportsbook, you don't have to be in Florida to join the party. Hard Rock Bet is also live in Arizona, Ohio, New Jersey, Indiana, Tennessee, Virginia, Illinois, Colorado and Michigan, with more states on the way. Download the Hard Rock Bet app today and and let's get the party started. Offered by the Seminole Tribe of Florida in Florida. Offered by Seminole Hard Rock Digital, LLC and all other states must be 21 or over and physically present in Arizona, Colorado, Florida, Illinois, Indiana, Michigan, New Jersey, Ohio, Tennessee or Virginia. To play terms and conditions apply. Concerned about gambling in Florida? Call 1833, playwise in Indiana. If you or someone you know has a gambling problem and wants help, call 1-809 with it in Ohio, call 1-800-my reset gambling problem. Call 1-800- gambler in Arizona, Colorado, Illinois, Michigan, New Jersey, Tennessee and Virginia. And now Superhuman Shack.
Shaquille O'Neal
I keep telling them not to say that I'm no superhuman. Believe it or not, I struggle with moderate obstructive sleep apnea, or osa, in adults with obesity. Moderate to severe OSA is a condition where breathing is interrupted during sleep, with loud snoring, choking, gasping for air, and even daytime fatigue. Let's just say it can sound a lot like this. Sound familiar? Learn more@don'tsleeponosa.com this information is provided by
Chad Millman
Lilly, a medicine company.
Superhuman Podcast Host
Imagine an Olympics where doping is not only legal, but encouraged. It's the enhanced Games. Some call it grotesque, others say it's unleashing human potential. Either way, the podcast Superhuman documented it all embedded in the games and with the athletes For a full year.
Mike Conti
Within probably 10 days, I'd put on £10. I was having trouble stopping the muscle growth.
Superhuman Podcast Host
Listen to Superhuman on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.
Clifford Taylor IV
A win is a win, A win is a win. I don't care what y' all say. Yep, that's me. Clifford Taylor iv. You might have seen the skits, the reactions, my journey from basketball to college football, or my career in sports media. Well, somewhere along the way, this platform became bigger than I ever imagined. And now I'm bringing all of that excitement to my brand new podcast, the Clifford Show. This is a place for raw, unfiltered conversations with some of your favorite athletes, creators, and voices that not only deserve to be heard, but celebrated. One week, I'll take you behind the scenes of the biggest moments in sports and entertainment, and the next, we'll talk about life, mental health, purpose, and even music. The Clifford show isn't just a podcast. It's a space for honest conversations, stories that don't always get told, and for people who are chasing something bigger. So if you've ever supported me or you're just chasing down a dream, this is right where you need to be. Listen to the Clifford show on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. And for more behind the scenes, follow Clifford and at TikTok Podcast Network on TikTok.
Sam J
Do you remember when Diana Ross double tapped Lil Kim's boobs at the VMAs? Or when Kanye said that George Bush didn't like black people? I know what you're thinking. What the hell does George Bush got to do with little Kim? Well, you can find out on the Look Back at it podcast. I'm Sam J.
Alex English
And I'm Alex English.
Sam J
Each episode, we pick a year, unpack what went down, and try to make sense of how we survived it, including
Alex English
a recent episode with Mark Lamont Hill waxing all about crack in the 80s.
Clifford Taylor IV
To be clear, 84 is big to me, not just because of crack. I'm down to talk about crack all day, but. Yeah, yeah, but just so y' all
Alex English
know, I mean, at this point, Mark, this is. This is the second episode where we've discussed cracks, so I'm starting to see that there's a through line.
Sam J
We also have AIDS on the table
Clifford Taylor IV
right now, so thank you for finishing that sentence. Yes. I don't think there's a more important year for black people.
Alex English
Really?
Clifford Taylor IV
Yeah. For me, it's one of the most important years for black people in American history.
Alex English
Listen to look back at it on the iHeartRadio app, Apple Podcasts or wherever you get your podcasts.
Chad Millman
Mike Since 2019, seven Derby winners, two went off at under 10 to 13 including Mage you just mentioned, were between 121 and 18 1. Twice in the past seven years, horses that won went off at odds of 60 to 1 or longer. In recent Derby races, the longest long shots have won just as often as the clear favorites. Any long shots people should be paying attention to.
Mike Conti
One of the horses that, that I keep kind of coming back to and we mentioned at the top of the show a little bit is Dan and Bourbon Japanese horse. This horse is a perfect three for three. The horse ran a mile and 3:16 before, so, you know, really close to today's distance and ran it in a pretty strong time. The horse is bred to go the distance and so I think at 20 to 1 is an interesting horse. I will say the last time I looked at the live markets and the live betting board, the horse was down to like 13 to 1, I think so already taking some money. Another one that's interesting to me at a price, number eight. So happy. This is a horse that's going to be much closer to the lead. Won the Santa Anita Derby and won pretty convincingly. Another relatively light lightly raised horse in here. So those are the two at prices. The third one, if you're looking for a third price horse, the lightest, the most lightly raised horse in the field, number 15. Emerging market for Chad Brown and Flavian Pratt coming out of a win in the Louisiana Derby, only his second start. Interesting to see, you know, even when Justify broke the myth that you had to run as a two year old in order to win the Derby as a three year old, he broke that myth back a couple years back now. But emerging market, if he were to find a way to win this race, would become the most lightly raised horse to ever win the Kentucky Derby with only having two prior starts to the Derby.
Simon Hunter
All right, I'm down to know what would be, what's going to be on your card. Who are you taking?
Mike Conti
Yeah, so my top choice, you know, as I, you know, I started doing homework obviously far before the post draw on Saturday, but once the post draw came out then I really started digging in and I probably did about three hours of homework on just Saturday night alone and I kept coming back to the Puma. I kind of mentioned this before. Number nine, the Puma morning line, 10 to 1. As you look at live odds right now, it does not look like we're going to get anywhere near 10 to 1 on the puma. But I think a horse, you know, again with a win over at the Tampa Bay Derby, ran really well in the Florida Derby just to get nipped at the wire by Commandment. I think that this is a horse that can continue to move forward as he has pretty much throughout his, his young life. So far, you've got Gustavo Delgado, who won with Mage back a couple of years ago. So he's going to be my top choice. You know, I think the Derby is always an interesting race. I think, you know, obviously it's a lot of fun. There's a lot of money to be made. The other horse that I'm drawn a lot to is Chief Wallaby. I mentioned when we were kind of going through some of these top five horses, I thought he didn't have the easiest or cleanest trip in the Florida Derby. Now, as we Talked about before, 20 Horse Field, you're going to have to figure out how to work out a trip. I think he's going to be able to be a little bit closer than some of these other horses like Renegade in here. I think if he works out a trip. Junior Alvarado obviously won the Derby last year. He knows how to work out a trip. I think that this horse kind of has somewhat of a similar running style to Sovereignty. And with Alvarado's experience, winning this on a similar type of a horse last year wouldn't put it past him. Another horse at decent odds of 8 to 1 that I'm including in all of my tickets.
Chad Millman
Does the Derby get treated by professionals? You know, we started talking about, you know, computer assisted wagering and Simon, you're seeing the growth in the space because of the opportunity with AI but does the Derby get treated like the super bowl by professionals? Do they care more about it? Do they care less about it? Is it more of a public play? How do professionals look at it?
Simon Hunter
Yeah, it's, it's a big deal in my. And the guys I talk to, but it's not like the NFL Super Bowl.
Mike Conti
It's.
Simon Hunter
It's different, right? Their, their dream scenario is that track. Like you just said, there's so many tracks across America, Chad. They just, whatever they have the inside info and the edge on, that's the biggest race and their favorite race, right? They're just this, this is for us. To me, in my opinion, right, the Kentucky Derby, it's for like the, the fans of, of horse racing. Someone like me who likes to bet I like to go to the track. Do I, you know, am I going to the track down in Delaware? No. Like, I want to be betting the Kentucky Derby.
Clifford Taylor IV
So that's.
Simon Hunter
That's me. Where my guy. He's probably heading down the track to Delaware, you know, so it's just. It's just very different. But I would do that is. That is true. Where it's like a Super Bowl. Yeah, it's. It's such a big deal in our world, where Kentucky Derby professionally, it's like. No, that's. That's for the general public. It's not for the. For the professionals.
Chad Millman
Mike, Same. Same point of view.
Mike Conti
Yeah, totally agree. I think, you know, it is. I don't think it matters to Simon's point from a professional standpoint. You're, you know, every weekend you're looking, where do I have the greatest edge when it comes to horse racing? But this is one that obviously brings the masses together. Right. Everybody knows the first Saturday in May, the Run for the Roses, the fastest two minutes in sports. People have parties around it similar to the Super Bowl. So I think it's, you know, I think Simon did a great job of describing it.
Chad Millman
All right, give us your exact as and your trifectas before we get out of here.
Mike Conti
Yeah, absolutely. So my exacta is going to look like I'm going to play what's called an exacta key box. So what that means for folks that aren't as familiar with horse racing, a key box means that I'm picking the exact. Excuse me. Means that I'm picking the first two finishers in the race. An exact key box means that I'm keying one horse, so I need that horse to finish in either first or second. It doesn't matter. And then I'm going to pick four or five other horses that can finish in the other position. So what this will look like is I'm going to do an exact key box. I am going to key number nine, the Puma. So that means that the Puma needs to finish in first or second. And then I'm going to use another four horses that need to finish in the other position from the Puma. And those horses are going to be number six, commandment number eight. So happy, number 12, Chief Wallaby, number 15, emerging market, and number 18, further ado. So that would then be an exact key box, keying the 9 with the 6, the 8, the 12, the 15, and the 18.
Chad Millman
Missed call. When's the next race? How does. How do you get a horse in the Kentucky Derby, what happens as an owner.
Mike Conti
So Ms. Call is actually running on Friday. So May 1, I am heading down to Churchill for her race. She's running in race three on Friday. She is 10 to 1 on the morning line. I don't think that the morning line's odds makers have given her the respect that she deserves. I'm biased. I'm part of the ownership group. But we like her chances in here, and so we'll see what happens with that. And, you know, in terms of getting involved in ownership in general, I mean, in today's world, it's really never been easier. There are so many of these different syndicates out there that you can become a part of. I think they can be great to get people introduced into, you know, ownership and what it's like. I think if you really want to get, you know, further down the road into ownership, you find the right people to kind of connect with you, form much smaller groups. I think our group is like eight people and you're talking about, you know, bigger chunks. You have a little bit more of a say and kind of the direction and where you go with the horse. You're, you know, having more regular conversations with the trainer and assistant trainers as to what's going on. So it's a. It's a really fun thing to be a part of.
Chad Millman
Well, listen, we're going to pile in on missed call, so those, those odds are going to shrink a little bit. So the pool is probably going to be down to 2 to 1 by the time Simon and I and his syndicate are done putting all that in there. Congratulations. That is just unbelievably cool. Mike Conti, thanks for coming on the show, brother. Great stuff. Congrats again on the big win. This has been Sharper Square, part of the Volume podcast network. Watch or listen on YouTube at Sharper Square. Like this video. Subscribe to the channel. Download us from Spotify, Apple Pods, wherever you get your pods rate. Review. Subscribe. Leave us five stars. Say whatever you want. Feedback is a gift. Until next time. Love you.
Mike Conti
Oh, my goodness. The Longest Shot has won the Kentucky Derby. Unbelievable upset.
Chad Millman
And now superhuman.
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Superhuman Podcast Host
Imagine an Olympics where doping is not only legal, but encouraged. It's the enhanced games. Some call it grotesque. Others say it's unleashing human potential. Either way, the podcast Superhuman documented it all, embedded in the games and with the athletes for a full year.
Mike Conti
Within probably 10 days, I'd put on £10. I was having trouble stopping the muscle growth.
Superhuman Podcast Host
Listen to Superhuman on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.
Clifford Taylor IV
A win is a win. A win is a win. I don't care what y' all say. Yep, that's me, Clifford Taylor iv. You might have seen the skits, my basketball and college football journey, or my career in sports media. Well, now I'm bringing all of that excitement to my brand new podcast, the Clifford Show. This is a place for raw, unfiltered conversations with athletes, creators, and voices that not only deserve to be heard, but celebrated. So let's get to it. Listen to the Clifford show on the iHeartRadio app, Apple Podcasts, or wherever you get your podcast. And for more behind the scenes, follow CLIFFORD and at TikTok Podcast Network on
Sam J
TikTok on the Look Back at It podcast from 1979.
Clifford Taylor IV
That was a big moment for me. 84 was big to me.
Sam J
I'm Sam J.
Alex English
And I'm Alex English.
Sam J
Each episode, we pick a year, unpack what went down, and try to make sense of how we survived it with our friends, fellow comedians and favorite authors like Mark Lamont hill. On the 80s, 84 was a while.
Mike Conti
I mean, it was a wild, wild year.
Clifford Taylor IV
I don't think there's a more important year for black people.
Alex English
Listen to look back at it on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.
Sam J
This is an iHeart podcast. Guaranteed Human.
Podcast: Sharp or Square (iHeartPodcasts/The Volume)
Episode Airdate: April 29, 2026
Hosts: Chad Millman, Simon Hunter
Guest: Mike Conti (handicapper, thoroughbred owner, Ithaca football legend)
This special Kentucky Derby preview episode brings together host Chad Millman, pro gambler Simon Hunter, and returning guest Mike Conti, a seasoned racing handicapper and thoroughbred owner. As the “most exciting two minutes in sports” approaches, the trio delivers insights into the Kentucky Derby betting landscape: from ownership experiences and track preparation, to the game-changing influence of AI and computer-assisted wagering (CAW). The conversation covers Derby contenders, betting strategies, and essential advice for both hardcore handicappers and casual race-day fans.
[02:10 - 03:36]
[03:40 - 08:20]
"You want to talk about, like, a feeling of euphoria and just something that it's hard to describe. It was that." – Mike Conti [04:22]
“…We were laughing after the race. We're like, how did we not bet the exacta with our two horses?” – Mike Conti [07:21]
[08:29 - 16:51]
“There is a boom right now, Chad, a money boom in the horse racing world because of AI... If you're just going to your local races right now, you're at an extreme disadvantage...” – Simon Hunter [08:35]
“…You hear about this because a horse enters the gate at 6 to 1 … that horse's off-odds might be half of that at three to one… As a better, if I’m expecting 6 to 1 and the horse crosses and I'm like, wait, I only got 3 to 1…?” – Mike Conti [11:40]
“There’s not one centralized body for everything to do with horse racing. Every track is different, every state is different.” – Mike Conti [12:24]
[13:05 - 16:51]
“In horse racing, if you bet on a horse at six to one, that line is going to move. There’s no getting the best of the number.” – Chad Millman [13:06]
[18:20 - 19:35]
“The Puma… is taking a ton of money in the early win pools…” – Mike Conti [18:20]
[19:53 - 27:45]
“It is for, the vast majority of these horses, the largest field they will ever run against… they've never experienced anything like that before.” – Mike Conti [20:10]
“I don’t think there’s a ton that separate these top five...you’ve got these five that are all really interesting.” – Mike Conti [27:41]
[32:46 - 34:56]
“If Emerging Market were to find a way to win this race, [he] would become the most lightly raced horse to ever win the Kentucky Derby…” – Mike Conti [34:46]
[35:01 - 39:58]
“My exacta is going to look like...I'm going to do an exacta key box. I'm going to key number nine, The Puma...with the 6, the 8, the 12, the 15, and the 18.” – Mike Conti [39:35]
[36:48 - 38:29]
“In my opinion…the Kentucky Derby, it’s for the fans of horse racing. Someone like me…I want to be betting the Kentucky Derby. My guy, he’s probably heading down the track to Delaware.” – Simon Hunter [37:46]
[39:58 - 41:21]
“In today’s world, it’s really never been easier…If you really want to get further down the road into ownership, you find the right people to kind of connect with you, form much smaller groups…It’s a really fun thing to be a part of.” – Mike Conti [40:07]
| Segment | Timestamp | |-----------------------------------------------|------------| | Owner's thrill, paddock insights | 04:22 | | AI & CAW in racing pools | 08:29-16:51| | Derby Week whispers, early money & scratches | 18:20 | | Derby race structure and dynamics | 19:53-21:52| | Analysis of top 5 Derby contenders | 22:04-27:45| | Value picks and live longshots | 32:46-34:56| | Mike’s picks, betting strategies | 35:01-39:58| | Ownership: how to get started | 39:58-41:21|
This episode delivers a comprehensive preview for Derby day, blending expert handicapping, betting strategy in the AI era, and the sheer excitement of racing culture. Whether you’re a casual Derby viewer or long-time horse player, Mike Conti’s insights offer both education and inspiration—while Simon Hunter and Chad Millman frame the evolving landscape of sports wagering. Their Derby advice? Understand the new reality of AI-era pools, respect the chaos and spectacle of the event, and above all, enjoy the ride.
Quotes and summaries attributed to speakers as per transcript. Ads and unrelated segments omitted for clarity.