Matthew Hiltzik (9:05)

Hello, Mike Pesca, man of mystery. So much more.

Mike Pesca (9:08)

So much more. Yes. Substance. And just what's the opposite of mystery? A little too much. So here's where I want to start. Take us somewhere meaningful in your career. So it doesn't have to be in law school, but kind of early on where you weren't exactly sure if you were going to be a political guy all your life, if you were going to be a media relations guy all your life, because you had a couple of these cross currents running through you and running through your biography. So was there a good time that we could situate ourselves in the Matthew Hiltzik crossroads story?

Matthew Hiltzik (9:43)

I was sitting in the noise center at Cornell University after my junior year of high school, and a gentleman sat down at the piano and started playing Come Sell Away and singing to it. And with that in the background with people begging the person to please stop doing it, but, you know, I sort of paused and use that.

Mike Pesca (10:04)

So you're saying that when we were 16 years old, I would sing really awful and people would beg to stop, but it would make about 10% of the people amused.

Matthew Hiltzik (10:13)

Well, that was the moment where I saw that you had a clear path to performance, engagement, substance, really appreciating the nuance of the moment and how to really capture an audience. And so from there I actually did go on to Cornell in the School of Industrial Labor Relations. And from there my thought process was that I would go to law school and hopefully be in House at a sports or entertainment entity within three years of graduating. That was sor of the formula. I was fortunate that my, my father took that path of having done that and, and then being at NBC. And David Stern, the late commissioner of the NBA was a, a dear friend of my father's and like an uncle, he had done the same thing and, and gone to the NBA. So those were really my two role models in terms of that path.

Mike Pesca (10:59)

Right. A lawyer who went into sports, a lawyer who went into media. And you saw that as a possibility for yourself.

Matthew Hiltzik (11:04)

Yes. I did not take a single course in political science or history while I was at Cornell. I had a ton about labor relations and labor economics and negotiations and psychology and then insurance and risk management and other things. I really took advantage of the full range of things, even design and environmental analysis in the human ecology school. So I really had a very well rounded education of things that I still remember took a, a sports arbitration course with a guy named Buck Briggs who had served on the NFL Management Council. So it was a great preparation and really along the lines.

Mike Pesca (11:44)

And the Cornell ILR School is the birthplace of League Commissioners, right?

Matthew Hiltzik (11:49)

Yeah, Mr. Commissioner Manfred and Bettman and several other notables. But it was the. I wrote for the Cornell Daily sun, which is only relevant because I was a year early in predicting that the Blue Jays would win the World Series. And I actually was in the. With a couple of my fraternity brothers at the local Tompkins County Community Hospital when Joe Carter hit his home run the last time the Blue Jays were in the World Series because one of the guys had gotten kicked in the ankle playing broomstick polo in instruments. And so that's how we ended up there. So those are the moments.

Mike Pesca (12:30)

This is how you. This is how you could tell the decade, because years later it would be Quidditch.

Matthew Hiltzik (12:35)

Yes. But that was sort of the path I had. I went to Fordham for law school. Tremendous place. I went straight from, from college there. It was a great opportunity to. To really learn again about a wider range of applications of a law school education. Got to see things from the other side of having Jeffrey Kessler, who was on the union side as an adjunct professor, had some others who. I learned about land use and zoning and was introduced to the power broker of a chapter One Mile, that talked about the Cross Bronx Expressway and how Robert Moses had manipulated things there just to piss off a political opponent. There were a lot of little nuances of things and that book was actually really, really helpful in giving me perspective on both how you could. You have to Have a vision, whether it was good or evil or some combination of both. Yeah, that was there. But to really understand how the political process works, how the media has a huge impact on things and how to deal with different constituencies.

Mike Pesca (13:43)

So at that point, did you say, okay, I see A plus B equals C. What this means is one day I'm going to represent an actor, his name is Alec Baldwin, and he's going to essentially play Robert Moses in a movie.

Matthew Hiltzik (13:54)

Wasn't quite the plan. I did not. I admired Alec from afar at that point, but didn't quite have the engagement yet. But it was my first summer after law school. I worked in the legal department at Paramount here in New York. And so that was really a real entrance into this world and understanding the world of entertainment. My second summer, I worked at Bankers Trust and got to see about how sort of the corporate world works and some other opportunities. And in between, I was a poll watcher for the Democratic party in the 94 election. And most meaningfully, I was a volunteer on the late Congresswoman Carolyn McCarthy's campaign when she ran for office out on Long island, where her husband had been killed and her son had been shot by Colin Ferguson, who was the Long island railroad shooter. And she was just a regular person who stood up for the fact that there wasn't anyone really standing up for them in Congress against the NRA to try to create changes to gun laws that had allowed for this terrible tragedy.

Mike Pesca (15:04)

What did you learn about politics from volunteering on that campaign?

Matthew Hiltzik (15:08)

It was the best campaign I was fortunate to work on, coordinated in 98 when Chuck Schumer and Elliot Spitzer won, and in 2000 when Hillary ran. But as an introduction, it was probably the purest form of politics. It was something where you got to do things of calling people on the phone, knocking on doors, handing out leaflets, and that was all in a very short couple of days that I even did this. But you saw that people were just so pleased and so enthusiastic and excited about. About the future congresswoman just putting herself in a position to make a difference. And it was something where all the things that we see now that can be so divisive and negative, none of that existed there because it was a community that was rallying around someone, one of their own, who really cared and was doing this for all the right reasons.

Mike Pesca (16:01)

When you then went to work on the Spitzer, Schumer and later Hillary Clinton campaigns, were you a paid staffer at that point?

Matthew Hiltzik (16:09)

Well, after I graduated law school, I had some opportunities to work in different law firms But I sort of realized that was not going to be the right fit for me at the time. I think it was going to be a little bit overly structured. And so I wanted to find a way to be able to sort of consider other options and through different circumstances. A guy named John Marino, who worked with Dan Cloris, they approached me about.

Mike Pesca (16:34)

Legendary PR guy.

Matthew Hiltzik (16:36)

Yes. And so he had. They had approached me because they were working with. John was a former chairman, the head of the Democratic Party in New York under Mario Cuomo. And he was helping them. Judith Hope, who had taken over as head of the Democratic Party in New York, helping her to find a communications person. And so the fact that I had done different writing, the fact that I had been involved in certain small ways in politics, and the fact that I had no allegiance to any of the 13 Democratic candidates running for statewide office that year, back when there were a lot of Democratic primaries and back when there were three Republicans holding statewide office here, they needed a press person. So I was willing to work for not that much money. I was a paid official staffer. I was the press secretary and eventually the deputy executive director of the state Democratic Party. And I got to see firsthand during the 98 cycle, I got to see the double standard for women where people totally underestimated Judith and what a strong command she had of the infrastructure that needed to be built at the time to engage with Democrats around the state. I got to see the fact that the chairman of the 12 biggest counties in New York totally underestimated who she was, what she was doing. Many of them ended up being indicted or going to jail over time. So they were not necessarily the ones we should have been looking up to. But Judith was very firm about the importance of primaries, not having a bunch of guys in a smoke filled back room choosing who the candidate should be. And Judith had a huge impact on my just view of both the political world, but also of understanding how similar things happen in business, how to treat people, how to be creative, how to understand audiences. And I still am very close to her this day, and she still raising hell on different issues. It's amazing.

Mike Pesca (18:31)

A lot of people who worked with Chuck Schumer and you weren't in his Senate office or his reelect office, right. You were working for him from the state party. But that is, that. That is a forged in fire type experience where you get a lot of insight from working for Chuck Schumer, but you also take a lot of incoming. What was your experience like?

Matthew Hiltzik (18:54)

Well, during the coordinate in 98, you had it was Schumer and it was Spitzer, and it was Peter Vallone who was running for governor. Obviously, the Schumer d' Amato race was really front and center. It was something where my family had had a connection with Chuck from when he'd been an assemblyman. I found an old letter that he had typed out to my grandfather, a little bit crooked. Thank him for his political contribution from 1966.

Mike Pesca (19:24)

I don't know about your grandfather. What did he do for living?

Matthew Hiltzik (19:26)

Was he a lawyer? Abe Hiltzik was a lawyer and did some things in real estate, but. And Abe Hiltzik was not a political person, so definitely one of his.

Mike Pesca (19:34)

He just. He just liked the cut of this young Chuck's jib.

Matthew Hiltzik (19:37)

I think it was definitely one of Abe Hiltic's friends said, abe, you need to write a check to this guy, and could you do it? And so he did.

Mike Pesca (19:43)

The assemblyman can.

Matthew Hiltzik (19:47)

And so. But the first time I met Chuck was in 1998, in March in a Holiday Inn in downtown Ithaca, which was at a meeting of the Democratic Rural Caucus and Conference. And I met him, and I introduced myself, and he said, are you related to Abe Hiltzik? And he had remembered that 23 years earlier, Abe Hiltzig had written him a check. And that was a great lesson in retail politics. It was a great lesson of seeing someone who really had cared about his constituents, about attention to detail. And, you know, he was just. He was tremendously wise and savvy. He had great people around him. There were a lot of people who worked on that campaign, as you noted, or worked for him later, who all went on to. To do a lot of really, really good things. We had a really fun moment during that campaign, was where I had sort of flagged for them. There was a moment in the campaign where Al d' Amato had gone. Had gone with. I think Ed Koch was in the room, too, and had called d' Amato a. And d' Amato had called Schumer a potshead and had made fun of Jerry Nadler's weight and called him Jerry Wadler. I believe he did. That's correct. And.

Mike Pesca (21:00)

And Trump has picked that up. Trump remembered that his keen, keen memory. Yeah.

Matthew Hiltzik (21:04)

Yeah. I'm not gonna. I'm gonna leave my Nadler feelings for a different time, but in that case, yeah, I didn't think it was appropriate language, but it was an interesting thing. I really never thought I was gonna be getting on the phone with York State explaining to them on background what a putz head was Explaining that that's not even really a word. But it was a great time to be there because there was such creative ways of trying to reach people. In the days before social media, Judith had built an infrastructure where at that point, it was more like weekly faxes that were going out to Democrats around the state. It was building up counties, county operations that had never really been in place before because of Republicans having overwhelming dominance in the state Senate and elsewhere in large swaths of upstate New York. And so Judith's infrastructure worked great. And the Schumer folks were really smart about recognizing who to engage with in local leadership. And in August of that year, the primary at that point was in September. And he went from when the polls changed from being registered voters to likely voters. Chuck went from third to first. And it was a real sign of things. It was also the earlier that year, in May, there was the Democratic state, the state Democratic convention, and the late Senator Moynihan, who was amazing just in his own brilliance in all these ways, he disappointed the crowds that instead of getting up and giving a whole speech about the importance and the context of this election where you had the chance to win back these statewide offices, he used the occasion to instead explain to everyone the importance of the issue of the conflict at that time between India and Pakistan.

Mike Pesca (22:48)

Yes, which I have great intellect, Moynihan, but maybe this wasn't the time.

Matthew Hiltzik (22:52)

Wasn't the perfect audience.

Mike Pesca (22:53)

The Kashmir region.

Matthew Hiltzik (22:54)

Yeah. The good news was that in the media room afterwards, he did then go through the explanation of the history of things, which was. But being around that was tremendously educational and informative.

Mike Pesca (23:06)

So to ask you about the Democratic primary where Cuomo was leading, Mamdani obviously had momentum. Was it the case? Cuomo strategy was, you know, as reflective of his generation. He'd go up on the air, he bought so many TV ads, whereas Mamdani dominated social media. Is that inherently smarter, a smarter move from mom Donnie because he mom Dani because he could get more touches, or was it just he was better? Zoram was better at social than Cuomo was at broadcast.

Matthew Hiltzik (23:44)

I think both have importance, but I think that we live in an age where, based on that sort of touch aspect of things, that I think that the social and digital component is more and more important. I think there still is relevance, because that touch of still seeing things is there. But in worlds where you can skip ads when you can, on the one hand, you're going to see less of it. On the other side, you're going to have much more targeted ads. That are much more precise. Like my, my approach is that from being a lawyer and member of the bar is that I'm going to be very fact based in my approach, but I'm also going to try to be precise about the audiences that we want to reach. And I think that the precision that's available to people through social and digital is really, is. Is very significant. You can get. My friend Gary Vaynerchuk will always tell you that those targeted ads on Facebook or, or on Instagram or wherever else it's going to be are hugely impactful if you understand your audience. And I do think that precision is pretty important. There is a factor also which is that the media enjoys the trend story of seeing someone who sort of explodes in a good way on social. But part of what happens sometimes that people don't necessarily look in the background of understanding how did those numbers increase? Where are those people? Are they people who are actually New York voters, or are they people who are just national or even international, as I think was the case with, you know, some of the things in the Mondame campaign. But the reality is once you have that momentum and you're able to show a significant increase in the followers, it's something where people notice that. And there are things that can affect the algorithms where those things can pop up more, they can be targeted differently. And so I think the answer to your question is I think you still need to have the other visibility. But I think in terms of really motivating people and especially younger voters, I think you have to look at the social digital as being more effective.

Mike Pesca (25:36)

Yeah, well, that was my other supposition that in terms of the younger voters. Yeah, everything you're saying is right. And Mamdani did really well, surprisingly well, in fact, shockingly well with younger voters, to the point where I think the old political science would say that's usually not a way to win an election. But in this case it was. Question is, doesn't. If we say that Instagram is so valuable and it's the way forward, doesn't that threaten an analysis where the younger candidate, or at least the candidate who gets the attraction of the young, that's who's on Instagram, they're going to seem to be doing a lot better. And except for this last campaign, it is usually the case that the older voter is more likely to come out than the younger voter.

Matthew Hiltzik (26:29)

Well, I think you have to break it down based on the race. If you. I am not a Bernie Sanders fan, but you can. That just certainly shows that his ascendants, just as Howard Dean's was in 2004 with MoveOn.org and a lot of things they did, it wasn't simply about age. It was about an understanding of the technology and it was an understanding of the reach that you can have. So I'm not fully sold on it just being about age of the candidate. I think that it's about a recognition, acknowledgment, embrace of the new ways to be able to reach people. I think it's still to be determined. I think while it's likely Madame will win, I think it's still to be determined because there's a lot of people who are out there whose opinions are not necessarily clearly expressed on social and digital. And so I still think there is a chance, and we certainly are seeing a tightening of the race. I think, as there's different things happening in these last couple weeks, I still think no one should presume the outcome because there's a lot of highly motivated people who, in the same way that there's a lot of visibility on social media, there's still a total lack of visibility of people and communities who are not as active on social right. When you look at big blocks of people, especially in Jewish communities in Brooklyn where they have kosher phones, cell phones that do not have access to it. When you look at other, especially different immigrant groups and people who may not have the means to have different types of smartphones and other aspects. Smartphones are sort of dated, you know, term, but like the idea that, you know, people who may not engage. You have people who come from countries who are fearful of sharing what their political views are. And I think that people shouldn't necessarily presume that anything's over. And when you. I still believe that the idea of getting people out to vote is still an art and a science. And it's something that, you know, there's been surprises before, so I wouldn't presume anything because in the same way that certain stuff is visible, certain stuff is not visible. And you should still be thinking about that, too.

Mike Pesca (28:41)

And we'll be back with part two of our discussion with Matthew Hiltzik tomorrow. Claude is an AI service that I so love. I use it for writing all the time. It's also excellent for coding, and it's improved my professional workflow. I am not going to say that all of the correspondence I get goes through Claude at some point. I mean, if you write in, you're going to hear from me, but just as an assist, saved me hours, hours and hours and hours. Claude is the AI for minds that don't stop at good enough. It's the collaborator. It's that actually understands your entire workflow and thinks with you, not for you. Whether you're debugging code at midnight or strategizing your next business move, Claude extends your thinking to tackle the problems that matter. It gives me suggestions I wouldn't have thought of and takes what I did think of and polishes it so that it's what I meant. Or I can tell myself, yeah, that's what I mean. Meant. And the thing that it does. Artificial intelligence. Right. What is intelligence but identifying connections where you didn't see them before? That's what I think. A key definition of intelligence is in my head. And when I think of intelligent humans now that we have intelligent machines. And that's what Claude does. Claude finds connections between all these sources that I wouldn't have found on my own, plus all the professional tools through MCP connectors, GitHub and Jira and HubSpot and Notion. If you work with those, you know what I mean. Ready to tackle bigger problems. Sign up for Claude today and get 50% off Claude Pro when you use my link. Claude AI the Gist. That's Claude AI the Gist right now for free. 50% off your first three months of Claude Pro. That includes access to all the features mentioned in today's episode. Claude AI slash the Gist, and now the spiel. Saturday Night Live has been pretty awful this year, but this weekend's episode had more decent sketches than the previous three combined. They led off with a quite funny New York mayoral debate sketch. A few of the jokes were very New York centric. I don't know if people in Kansas are going to laugh at jokes about the sandwich quality at Gristeedis. But then again, they spared the people in Kansas an even better potential joke about the narrowness of the aisles in Gristeedis. You just give me the word. I got a tight 10 on Gristeedis. The thing that confused me about SNL's debate sketch was the casting and how they chose to portray the three remaining mayoral candidates. Curtis Sliwa they pretty much nailed. It's hard not to. They called in a ringer, Shane Gillis, who's not from New York, he's from Pennsylvania, but he did a good enough accent. He portrayed Sliwa's actual, or I should say, supposed actual history. I'm thrilled to be here and not getting shot in the back of a yellow cab five times by the Gotti's and Gambinos as I was famously in 1992, 1993 and 94. But I'm the right choice to be your next mayor. No offense to my opponents, Mr. Cuomo, and I believe I'm saying this right. Zoltar Rob Zombie, Zoran Mamdani, who will be the next mayor and will give SNL plenty of fodder, was played by Rami Yousef, another ringer. Yousef wasn't particularly great at his impression. He doesn't look that much like the Ugandan born ethnically Indian Gujarati and Punjabi mummy. Yousef is in fact Queensborn with family from Egypt. But I guess to snl, that's close enough in that both the candidate and the actor are Muslim and what the census doesn't call a minority, but what many people in the United States will think of and what mom dummy refers to himself as Brown. Here was Yousef. And I know some of you are.

Matthew Hiltzik (32:55)

Out there scared of the idea of a young socialist Muslim mayor, so allow me to put you at ease by smiling after every answer in a way that physically hurts my face.

Mike Pesca (33:07)

Here is Mom. Donnie.

Matthew Hiltzik (33:08)

I want to speak to every child who grows up in New York marked as the other, who is randomly selected.

Mike Pesca (33:14)

In a way that rarely feels random.

Matthew Hiltzik (33:16)

Who feels that they carry a stain.

Mike Pesca (33:18)

That can never quite be cleaned. Okay, fine. Then there was Andrew Cuomo, played by Miles Teller, 100% non Italian American, as far as I know, playing 100% of the stereotype of the Italian American. Here is Miles Teller. I am born bred New Yorker.

Matthew Hiltzik (33:37)

I love it here.

Mike Pesca (33:38)

I know this city like the back of a woman's back. Mamma mia. Look, it's a good impression of some Italian guy who's not Andrew Cuomo. And it's clear there are no sensitivities about portraying some goomba as a garden variety gavon, the way there would be about mis portraying a candidate from a marginalized community. But I live in America in 2025. I get it. It's not new. But the real Andrew Cuomo, and this is my point, is eminently mockable for the way he speaks. Not what he says, but the way he speaks. Okay, maybe not mockable, but it's really distinctive. Listen to this. I'm Andrew Cuomo, and unless you've been living under a rock, you probably know that the Democratic primary did not go the way I had hoped. To the 440,000 New Yorkers who voted for me, I think sincere thank you. Thank you for believing in me, in my agenda, and in my experience and I am truly sorry that I let you down. At one point, one of Cuomo's commercials veered dangerously into almost auto tune territory. I see a new day just over the horizon with 5,000 more cops on the beat, the homeless off the streets, and 500,000 new officials affordable homes. But there is none of that in the Teller impersonation. I got us through Covid and then yada yada yada, Hong Kong squeeze, squeeze. Anyway, I'm back now. If you're a big fan of the gist, it's probably despite my attempts at both singing and voice work. But it seems to me that a master impressionist, or even someone who is trying hard and has a coach, could do a lot better with a Cuomo impression. And that brings me from sketch comedy critique to actual political insight. Andrew Cuomo is, as I've said, incredibly distinctive sounding. Here is a master impressionist, Kyle Dunnigan, doing an actual Cuomo impersonation.

Matthew Hiltzik (35:39)

One night before a show, I saw him rubbing Vaseline down there and I said, gramps, why do you do this? He says, I do this. So when I go to the audience giving them the polish car wash, it moisturizes the dry skin. He was doing this for others.

Mike Pesca (35:58)

So you wear a mask for me.

Matthew Hiltzik (36:01)

And I wear a mask for you. Okay, next question.

Mike Pesca (36:03)

The fact that the Cuomo impressions trotted out a few different times by a few different actors on snl, actors whose Cuomo impression skills are ooh nots gave me an insight into what New Yorkers who know this man well were governed by him for many, many years and during the pandemic, who were treated to the ubiquity of his press conference, what they actually think of him. And it tells me that the impression they formed of him by the impression is not much. I don't mean that they have a low impression of him. They don't really know him. He just comes across as a stereotype. And that's okay. I don't say this to offend him or anyone or Italians. I say it to underline an odd indistinctiveness to this man who by all measures should come across as unique. The New York crowd who laughed at the gristed sandwiches are wet joke because it's an in the know reference, also laughed at a very inaccurate Cuomo impression. I do think if SNL had trotted out an Ed Koch impression in 1979 that just portrayed him as a kvetching Jew and not distinctively as Ed Koch, who I used to call the human dial tone. I don't know what you mean. You wouldn't have gotten the kind of big laughs that this dime a dozen schoolbots Cuomo impression delivered. Because New Yorkers don't really know Andrew Cuomo and that's not their fault. That's his fault. He is off putting and unlike Momdani, he's not someone that you at this point want to get to know better. And I think tomorrow the polls will reflect that. I got us through Covid and then yada yada, Hong Kong squeeze, squeeze. Anyway, I'm back. That's it for today's show. Corey War is the producer of the Gist. Jeff Craig runs our Social. Kathleen Sykes helps me on the Gist list very much. And Michelle Pesca helps us all so very much see the error of our ways and the wisdom of our future. And thanks for listening. And you can be on one block and there are Hasidic Jewish people. You go to the next block, it's Caribbean. You go to the next block, it's, let's say, Italian. My mother Matilda. All on top of each other. Yes, it creates tension. It can be bumping into each other, but we make it work. We make the American dream work.

Matthew Hiltzik (38:52)

Mom.

Mike Pesca (38:53)

Dummy. I don't know if he understands this quick story. I was governor and there was a bridge and I named the bridge after my father. It's not much of a story, but it was a quick story. We've all done it. Stock our fridge with leafy greens and good intentions only to have our future self sacrifice. Quality nutrition for the convenience of takeout. Keep your body and mind nourished all day with a whole body meal shake from cachava. It's got 25 grams of protein, 6 grams of fiber, greens, adaptogens and so much more. But the best part, it actually tastes delicious. With six indulgent flavors to choose from, it's easy to make a superfood packed shake from chocolate, vanilla and chai to matcha, coconut, acai and strawberry. You've got endless ways to personalize your cachava. Whether you prefer it straight up or enjoy adding fruit, peanut butter, nut milk or even iced coffee. With every two scoops of Cachava you're getting 85 superfoods, nutrients and plant based ingredients. Your future self will thank you. Go to kachava.com and use code health for 15% off your next order. That's Kachava K A C-H-A-V-A.com code health for 15% off. Marketing is hard, but I'll tell you a little secret. It doesn't have to be. Let me point something out. You're listening to a podcast right now, and it's great. You love the host. You seek it out and download it. You listen to it while driving, working out, cooking, even going to the bathroom. Podcasts are a pretty close companion. And this is a podcast ad. Did I get your attention? You can reach great listeners like yourself with podcast advertising from Libsyn Ads. Choose from hundreds of top podcasts offering host endorsements, or run a pre produced ad like this one across thousands of shows. To reach your target audience in their favorite podcasts with Libsyn ads, go to Libsynads.com that's L I B S Y N ads.com today.