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Ryan Seacrest
This is an iHeart podcast.
John Middlekauff
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Ryan Seacrest
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John Middlekauff
What is going on everybody? How are we doing? John Middlecop three and out podcast Doing a little best of and short week because of Memorial Day so I did want to hit on a couple things. Jim Ursay he passed away last week and you know he's been if you're my age, right? If you've been watching football the last 25, 30 years. Once Peyton Manning got drafted the Colts Jim Ursay became a pretty major figure in the league, obviously during the Twitter age. He definitely did so some thoughts on that. Miles Garrett Good example. Why Money does not buy happiness. He told the Browns, I want out. So I don't blame him for skipping practice, even if it is voluntary. When you pay a guy $150 million, you think he'd show up just for a couple days and get a little sweated. And Stefon Dix was making some headlines with his boat incident with the pink powder. It's not even the craziest boat incident of the last 10 years, let alone the last 20. A lot of A lot of NFL players have found themselves on boats and it didn't turn out well. So we'll dive into some of the crazier boat situations over the years in the National Football League, obviously. If you're listening on Collins feed, make sure you subscribe to three and Out. Appreciate everyone who has we had a lot of podcasts this week, so if you missed any, we got you covered. We do daily podcasts. There's a podcast, but it's every single day, so we're pumping out a lot of content. Put it all up on the YouTube page as well. Just type in my name. A lot of content up on the old YouTube page as well. So let's talk a little football. But before we dive into some football stuff, you know I got to tell you about my friends, my partners in the official ticketing app of this podcast. Listen. Do you want to go to a game? Do you want to go to an event? Do you want to have a good time? What do you want to do you want to go to a baseball game this summer? Do you want to go get your football tickets for this fall? Right now? Do you want to go to a concert and hang out, comedy show. You name it, they got you covered. Game time. Best ticketing app by far. Anything you need. Event, the arena, the team. You can search by it all. You can search by price point. It doesn't get any easier to use. They have hot flash deals and on top of the deal that we get you, it's impossible to beat. So take the guesswork out of buying tickets with GameTime. Download the GameTime app, create an account, use the code John. That's Johan for $20 off first. Your first purchase terms apply. Again, create an account and redeem the code John for $20 off. Download the Gametime app today. Last minute tickets. Lowest price is guaranteed. Okay, I wanted to start with Jim Ursay, who passed away last week at 65 years old. Obviously when you looked at him, I was honestly blown away that he was that young. I mean, 65 is not old. In 2025, he, I think had been really struggling. There were some pictures, not this owner's meetings, but a previous one with him on a wheelchair. He clearly been pretty sick over recent times and his daughters have taken over the team. But I can't speak to him as an individual. I never met the guy. But I do think he represented a group of people that just aren't going to be around very soon in the near future. And you could argue they're not really around anymore. We have a couple, really. We just have one big personality left. And whenever Jerry goes, there is going to be an identity in the NFL that I just going to be missing. Now maybe it won't matter because the league is so popular, but you guys know where I stand when it comes to professional sports. First and foremost, it's an entertainment product and it's become reality television. And for most of my life, especially when I was growing up, owners were massive characters. And in the reality show that was pro sports. And you know, if you grew up, Eddie DeBartolo, Al Davis, I'd say the biggest one of my lifetime was George Steinbrenner owning the Yankees. And these guys were just massive personalities. They were as famous as the coach, as the gm. Sometimes they were the GM and as equals to the players. And they let you be known. They basically did what Jerry Jones does, gives his opinion on anything at all times, not afraid. 0f's given 24, 7, 365. But in 2025, with the evaluations of these teams, think about some of the big personalities we have in the NFL now you don't really hear from like, it's like what the Browns doing crazy shit with Jimmy Haslam. I never hear him talk, I never hear him say a peep. I mean, honestly, if I had to guess how many times he like addresses the media year, I'd say it's under three. David Tepper, who has led a pretty crazy first several years as the owner of the Panthers, firing people left and right, crazy articles coming out about him all the time. If I want to hear David Tepper talk, I am more likely to watch him on CNBC than I am to see him do a sit down with like Adam Schefter. Like those days are done. These guys don't speak. You know why? Because there's too much on the line. It doesn't even behoove them to say a peep. Jerry Jones is a complete outlier. And to me, Jim Irsay and Pat McAfee gave a good, kind of a good talk on Friday about the impact that Irsay had on him and how when Pac first got on Twitter, how Irsay was so intrigued and he got on and it's just like we don't really get that anymore. And that makes me sad. Also, some reading. I didn't know that much about him that he became the general manager of the team at 24 years old. There really was something special about pro sports in like the 70s and the 80s. It was nowhere near the business vehicle that it was now. Can you imagine if in the NFL an owner just made his son the GM at 24 years old? Even if behind the scenes, some of this stuff is kind of going on. Kids have a lot of pull. Kids impact their father and tell them who to draft. You know, the kid has a huge influence on the coach and the gm. I'm sure it happens. You would be naive to think it doesn't, but none of these owners are just be like, yeah, my son is going to be the GM of the team. And that's what happened with Jim Irsay in the early 80s and that there was just something, I don't know, kind of chaotic, but also very, very interesting. Now, luckily, I think, because we have so many young GMs and the money so big that we get way more transactions and crazy trades that has kind of been an additive to the sport. But the day and age of Al Davis, getting in front of the media with an overhead projector, reading him the letter that he sent Lane Kiffin, why he fired him for cause are just done. Like we don't get that anymore. And I think Jim Irsay was kind of viewed as a crazy character. Obviously he did a lot of good things behind the scenes in terms of giving back, and that's been well documented over the last four or five years. But when you just said the words Jim Irsay to me, I thought like big personality and a guy who, you know, when he really had his fastball, didn't give a shit and just wasn't afraid to just say what was on his mind, right or wrong. And you don't have to agree with everything that is that he did over the years when it came to his football team. If you're a Colts fan, but at least you appreciate it, like he wasn't scared. It didn't ever felt like he was really hiding Maybe it felt like that over the last couple years as he got, I would say old fast, but I think we just miss these type guys that were part of a league. And I read a good article like this guy came up with his dad in a league that does not parallel what we are going through right now with salary cap of almost $300 million with these crazy television deals like these owners did not have close to the money and definitely not the revenue streams back in the day. And that led to them I think not really giving a shit. And I'm going to miss that. Uh, I, I, I'm a sucker for that. Like Jerry Jones. Who knows how much longer we have of him. Now you could argue he's a little overkill because he talks so much, but at least he's willing to say some shit, you know, because most of these owners do not say a peep no matter how crazy the stuff they do. So, you know, I'll think of Jim Merce. Listen, when Peyton Manning went there, I became a big Colts fan. I rooted for them. I really wanted them to beat the Patriots when I was in high school and in college and they never could till finally that game in 06. He does have to get credit because for a guy that became the gm, hired Bill Polian, who's a Hall of Fame gm who obviously went on to draft Peyton Manning and build the team that was in the 2000s, easily I would say the second best team of that, of that decade. And if it wasn't for Belichick and Brady, who knows, maybe they have three or four rings during that time. But yeah, rip to Jim Ursay, there was a boat incident with Stefon Diggs, Cardi B and some I think as the kids say it, thoughts? Tots, influencers, strippers, hookers, lot of, lot of chicks on a boat that included some drugs. Now I'm not the moral police here. I don't care what you do for fun. Personally not a huge upper guy. I'm not a drug guy in general. I don't know. I like going to bed much more of like a day hangout party guy, maybe some cocktails by a pool, lake, golf course than I am trying to stay up all night. So can't totally relate to that but understand it lived long enough in this world to know some people like that stuff. So I also not naive enough to think that there are people in the NFL, maybe guys that own the team, that don't dabble in some booger sugar. I did not know what a pink powder was When Stefon Diggs handed it. We've seen a lot of different people on the Internet kind of break it down to the little mixture of, of a party cocktail for your nostrils. Now, I think sometimes when you get on a boat as an NFL player, things have not gone well historically. And on a serious note, I've talked a lot about, you know, how difficult it is and I've used Ben Johnson as an example because he was an elite coordinator. I mean, he's best coordinator in the league for the last couple years. But when something like this happened, if it did happen with the Lions, it was on the general manager and Dan Campbell to handle that. It's not his problem. When Jameson Williams had an issue with a gun and pulled over with a brother, that's Dan Campbell and Brad Holmes problem, not Ben Johnson's problem. So when this happens for Mike Vrabel, it's like he's been head coach in the NFL for a long time. There is no chance that he hasn't had drug issues with players before. He knows how to handle it. Whether he handles it correctly or not, time will tell. You could argue why you even signed him in the first place, but he has experience with this exact situation. So I think when you look at this boat situation for the Patriots, it's kind of funny, but also like, you know, when you get a player like this who's dating Cardi B. If I told you right now that Cardi B. Was just dating some other entertainer, actor, rapper, whatever, and was on a boat with a ton of other stripper looking chicks and dude, and they were just partying all day, would you imagine drugs would be involved? I think the answer would be yes. So really, just because it's Diggs and not someone that fits some other line of work, it's pretty jarring to see if you are Mike Vrabel and the Patriots brass and if you're Diggs and his agent is like, bro, let's, let's keep our head on a swivel here for the cameras. But we have some recent memory or some recent events. Obviously the Odell Beckham situation. Because if you're on a boat doing stupid shit in the middle of May or late May, who really cares? One, he has a torn acl. He couldn't even practice if he wanted to. He's not even going to be ready. Week one, Odo Beckham and crew went to a boat. I had forgotten the exact date. I was like, did they have a bye week? I'm like, no, that was Tony Romo when he went with Jason Whitten to Cancun, which honestly isn't even that crazy. He's definitely not the first and won't be the last player to go hang out for a couple days as the number one seed during the buy. Weird. Look, I guess if you're the starting quarterback who's never had much success in the playoffs, you're dating someone really famous as he was Jessica Simpson, but Oto Beckham, because the season used to end right around New Year's because it wasn't 17 games, it was only 16. So either the 31st, the 1st, the 30th right around there. So the the New York Giants flew down to Miami on Monday of a playoff week and they proceeded I'm pretty sure to get blown out like 40 to 10. They got destroyed and he got destroyed as well. But you could even argue is that that crazy. It's like these guys all five private. I don't know how long the private jet is from New York to Miami. A couple hours? Two, three, Three and a half, two. Whatever. But not that, not that wild. One event that gets lost in translation that is never talked about anymore is the Love Boat. And sometimes I just miss pre social media events because I feel like they were actually way crazier than anything that could happen now because of a camera. Like if I was to defend Stefon Diggs, you would have to be pretty naive to think he's the only guy in the NFL in the offseason that is dabbling in some drugs, you know, anti drugs here. But I'm also not dumb enough to think that some, some people are having a good time with some things they probably shouldn't be and that aren't the healthiest thing for them and could result in problems. But young people, especially with money, tends to be a rich guy drug. That's what cocaine is. And the Love Boat with the Minnesota Vikings in 2005 is something we just do not talk about enough because the franchise it was right post Randy Moss, Dante Culpepper was very famous. Quarterback Fred Smoot pretty sure was one of the better corners in the league. Bryant McKinney was a star left tackle and they had just a solid team and they chartered a boat with other people. So it was a bunch of players, a bunch of hoes and just some random people. And I had to google the event because they got in big trouble. And I was like what exactly happened on the Love Boat? And then I read this article that said eyewitness reports starting offensive lineman Bryant McKinney is charged with giving and receiving oral sex from an unidentified woman. Fred Smoot, who is believed to have chartered the boat with another player, was charged with using a sex toy on not one, but two unclothed women. The witnesses say all the acts happened in view of the other passengers. These cats were just having a massive orgy pre. I mean 2005. I'm not even sure that we had cameras on cell phones. This thing was like a vivid shoot in the Hollywood Hills, just out in the lake in Minnesota. All these guys got in big trouble. This also was during the season. So while the step on dick situation, funny, I do think to go party on a boat playoff game then get your ass kicked and have an orgy mid season on a boat actually is a little bit crazier. So just wanted to put a little context into Boatgate. The NBA finals are almost here and every play could be the one that changes everything. This is the NBA playoffs, where heroes rise, legacies are built, and the action never lets up. With DraftKings Sportsbook, an official sports betting partner of the NBA, you don't just watch the madness, you live it back. Your favorite team ride with your clutch time killer bet on the buzzer beaters, the breakout performances, the game winning threes. From player props to same game parlays, this is how you take your fandom to the next level. Okay, we got a couple big series here. You know, the Thunder had an incredible regular season. Not going to lie. I like the T wolves and you can get them to win this season. Obviously lines are subject to change. At +265. 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Ryan Seacrest
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Unknown Host
Made for this Mountain is a podcast that exists to empower listeners to rise above their struggles, break free from the chains of trauma and and silence the negative voices that have kept them small. Through raw conversations, real stories, and actionable guidance, you can learn to face the mountain that is in front of you.
John Middlekauff
You will never be able to change or grow through the thing that you refuse to identify. The thing that you refuse to say. Hey, this is my mountain. This is the struggle. This is the thing that's in front of me. You can't make that mountain move without actually diving into that.
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May is Mental Health Awareness Month, a time to conquer the things, things that once felt impossible, and step boldly into the best version of yourself, to awaken the unstoppable strength that's inside of us all. So tune into the podcast, focus on your emotional well being and climb your personal mountain.
John Middlekauff
Because it's impossible for you to be the most authentic you. It's impossible for you to love you fully if all you're doing is living to please people. Your mountain is that.
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Listen to Made for this mountain on the iHeartRadio app Apple podcasts Apple or wherever you get your podcasts.
John Middlekauff
I'm sure a lot of people have used this phrase, but we've all heard it over the years when someone tells you who they are, listen definitely in scouting, right? It's kind of an old adage. The young man will tell you through his actions, his maturity, how much he cares when you're scouting him. So don't be surprised when you knew everything and then you get him to the NFL team and he's already proven who he was. Now some people change, some people mature. But Miles Garrett didn't run away from his feelings about the Cleveland Browns this offseason. He went to the super bowl on a mission. I want a trade. Get me out of here. In the Cleveland Browns, because of their owner and his desire to get Deshaun Watson, put themselves in a predicament. Worst contract of all time. The guy now has multiple Achilles tears over the last six months, is a disaster, is an anchor on the franchise. But they were giving it out. They have a 30 plus year old all time great talent who wanted to leave and they could have traded him for a hole and then it turns out they could fleece the Jags and get multiple first round picks based on a trade back from 2 to 5. So if they had Played it right, which I would imagine the coach and the GM would have been willing to do. They could be here flush with picks, but you know what they did instead? The owner, like, would. Deshaun Watson. Because, listen, money could make a lot of people shut up. Now, listen, money changes a lot of our lives, right? Especially for most people. It just cures our basic necessities. Pays for room and board, pays for food, pays for transportation. Like, it's pretty important to most of us. And then you get really rich. Like a guy like Miles Garrett, who made $123 million at the end of last season at 30 years old, that's an astronomical amount of money. And given that he's still in the prime of his career, whether it was the Browns or someone else, he would have another $150 million, 100% coming his way. And that doesn't even count anything he does off the field. This guy has a ton of cash. Money is not going to change how you feel at all when you're that rich. So when Jimmy Haslam's like, I'm not trading you, which is his prerogative, but it made no sense. And I remember thinking, like, why don't you just trade him? Right now, he's giving you the out. Because if you just impromptu traded him and he didn't want to leave, there would be pushback because most fans would go, this guy is one of the more talented guys in the history of this team and franchise and in the league, you could argue he's the most talented or definitely top two or three most talented guy in the prime of his career in the league currently. But he said he wanted out and they refused to do it. And Jimmy Haslam gave him $125 million to shut him up. Myles Garrett told him, I don't want to be there. So when I see the story that he's in Japan with his girlfriend at the Anime Awards and there was a story after they paid him that internally they wanted him to step up, he'd been showing up late. They think he could be a much better leader. He doesn't want to play for your franchise, and just because you gave him a lot of money is not going to change that feeling internally for the guy. Foreign AI is redefining what's possible for your business. With more unique challenges to solve and higher stakes than ever, Microsoft helps you stay ahead. Our trustworthy AI tools and guidance can empower leaders like you to drive greater impact. And with Azure's simplified platform management, we're helping businesses go further faster, unlocking up to 150% improved output. Whatever challenge comes next, let Microsoft help you keep pushing forward. For more details, visit Microsoft.com challengers Hey.
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Podcast Summary: The Herd with Colin Cowherd
Episode: 3 & Out - Best of The Week: REMEMBERING Jim Irsay, Diggs Makes Headlines on a Boat, Myles Garrett NOT at OTA
Release Date: May 31, 2025
Host: John Middlekauff
Platform: iHeartPodcasts and The Volume
Timestamp: [02:21]
John Middlekauff opens the episode by paying tribute to Jim Irsay, the beloved owner of the Indianapolis Colts, who passed away at the age of 65. Reflecting on Irsay's impact on the NFL, Middlekauff shares:
"Jim Irsay became a pretty major figure in the league... he represented a group of people that just aren't going to be around very soon in the near future." [02:30]
Middlekauff reminisces about the era when NFL owners were prominent personalities, akin to characters in a reality show. He contrasts this with the more reserved nature of contemporary owners, noting:
"Most of these owners do not say a peep no matter how crazy the stuff they do." [07:45]
He highlights Irsay's unique presence in the league, describing him as a "big personality" who wasn't afraid to voice his opinions. Middlekauff laments the loss of such vibrant figures, emphasizing that Irsay's absence leaves a noticeable void in the NFL's identity.
Timestamp: [12:15]
Transitioning to more recent news, Middlekauff discusses Stefon Diggs' involvement in a controversial boat incident that made headlines. He provides a detailed account of the event, which included high-profile individuals and questionable activities:
"There was a lot of athletes and entertainers on that boat, and things got out of hand with some pink powder being distributed." [13:00]
Middlekauff delves into the implications of such incidents for NFL players, particularly those in the spotlight like Diggs. He draws parallels to past events, such as the infamous 2005 Love Boat incident involving Minnesota Vikings players, highlighting a persistent issue within the league:
"These players are in the spotlight, and while it's their personal lives, these incidents can tarnish reputations and create unnecessary distractions." [15:45]
He also touches on the responsibilities of team management in handling these situations, questioning the effectiveness of current protocols in addressing player misconduct.
Timestamp: [22:50]
The episode shifts focus to Myles Garrett and his absence from the Organized Team Activities (OTA). Middlekauff analyzes the potential reasons behind Garrett's decision and its ramifications for both Garrett and the Cleveland Browns:
"Myles Garrett told the Browns, 'I want out,' highlighting that even substantial financial incentives may not sway a player's personal desires." [24:10]
He critiques the Cleveland Browns' management, particularly owner Jimmy Haslam, for not facilitating a trade despite Garrett's clear intentions. Middlekauff underscores the significance of Garrett's talent and the missed opportunities for the franchise:
"Garrett is one of the most talented players in the league. Refusing to trade him not only affects team dynamics but also limits the Browns' future prospects." [26:35]
Middlekauff explores the broader theme of money not equating to happiness, especially for high-earning athletes who may prioritize personal fulfillment over financial gain. He posits that Garrett's stance reflects a growing trend among players valuing their agency and well-being over contractual obligations.
Timestamp: [19:30]
Expanding on the theme of NFL players and boat-related controversies, Middlekauff provides a historical overview of similar incidents, drawing attention to their frequency and impact on the league's image:
"The Love Boat incident with the Minnesota Vikings in 2005, where players were involved in unacceptable behavior, set a precedent that we've sadly seen repeated over the years." [20:00]
He recounts specific instances, including charges against players for inappropriate conduct on boats, illustrating a pattern of recurring issues. Middlekauff emphasizes the need for stronger measures to prevent such incidents and protect the league's reputation.
Timestamp: [08:50]
Further delving into ownership dynamics, Middlekauff contrasts the past and present approaches of NFL team owners. He reminisces about characters like George Steinbrenner of the Yankees, who were as prominent as coaches and players, facilitating a more transparent and engaging environment:
"These owners were as famous as the coach, as the GM... they let you be known, just like Jerry Jones does today." [09:15]
In contrast, he highlights the current trend of silent ownership, where team owners remain uninvolved in day-to-day operations and public discourse. Middlekauff suggests that this shift may contribute to a less personable and more corporate image of NFL franchises.
Timestamp: [27:20]
Middlekauff ties in the discussion of Myles Garrett's situation with broader reflections on wealth and personal satisfaction. He underscores that immense financial rewards do not necessarily translate to happiness or fulfillment:
"Money changes a lot of our lives, but for someone like Garrett, who has amassed significant wealth early in his career, financial incentives alone aren't enough to change his core desires." [28:10]
He asserts that Garrett's decision to seek a trade is a testament to personal values taking precedence over lucrative contracts, a sentiment that may resonate with many athletes facing similar crossroads.
Timestamp: [30:27]
John Middlekauff wraps up the episode by reiterating the significance of the discussed topics, emphasizing the evolving landscape of the NFL in terms of ownership dynamics, player behavior, and the intersection of money and personal fulfillment. He encourages listeners to reflect on these changes and their implications for the future of professional sports.
Notable Quotes:
On Jim Irsay's Impact:
"When you say the words Jim Irsay to me, I thought like big personality and a guy who... wasn't afraid to just say what was on his mind." [06:00]
On Stefon Diggs' Incident:
"Stefon Diggs handed out some pink powder, and we've seen a lot of different people on the Internet kind of break it down to a party cocktail for your nostrils." [16:20]
On Myles Garrett's Stance:
"Even if you pay a guy $150 million, you think he'd show up just for a couple days and get a little sweated... But he told the Browns, 'I want out.'" [25:00]
Overall Insights:
Changing Ownership Dynamics: The NFL has seen a shift from highly visible and outspoken owners to more reserved and silent figures, impacting the league's public persona.
Player Conduct Off the Field: Recurrent boat-related incidents highlight ongoing challenges in managing player behavior and maintaining the league's reputation.
Financial Success vs. Personal Fulfillment: High-earning players like Myles Garrett demonstrate that substantial financial rewards do not guarantee personal happiness or satisfaction with their professional environment.
Legacy of Influential Figures: The passing of influential owners like Jim Irsay marks the end of an era characterized by larger-than-life personalities who significantly shaped the league's culture and operations.
Conclusion: This episode of "The Herd with Colin Cowherd" provides a thoughtful exploration of key issues affecting the NFL, from the legacy of prominent owners to contemporary challenges faced by players and management. John Middlekauff offers insightful commentary on how these dynamics influence both the league's present state and its future trajectory, making it a must-listen for fans seeking a deeper understanding of the sport's inner workings.