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The Knicks, the Media, and the Money: Inside the Business with Schaap and Checketts

May 27, 2025 The Knicks, the Media, and the Money: Inside the Business with Schaap and Checketts

In a conversation with host Michael Goldstein, ESPN’s Jeremy Schaap and former Madison Square Garden President & CEO Dave Checketts revisit the New York Knicks’ past, the current excitement around the team’s long-awaited run, and the behind-the-scenes business dealings that make it all happen. Below are edited highlights of the conversation.

 

Michael: Dave, New York is Knicks crazy right now and this is the furthest they’ve gone since you were the President & CEO of MSG way back in 2000 against the Pacers. What are your thoughts on what’s happening?

Dave: The famous series of ’95, when Reggie Miller brought them back from down 7 with 58 seconds left with tremendous play, was so humiliating in so many ways I cannot describe. That series in ’95 broke us.

Shortly after that series, Pat Riley resigned. He had a year left on his contract and I just started getting calls from Southern Florida that this negotiation had been going on for months. In fact, I got a call that said, “I have a copy of the contract that was exchanged the night of the Reggie Miller Game.” So, in other words, our coach’s heart was completely out the door.

So that was the start of a real change for us and a tampering trial in front of (former NBA commissioner) David Stern as the mediator. I was on the witness stand for 8.5 hours.

Michael: Jeremy, you covered a lot of the 90s Knicks teams when they were very good for the last time before now. What’s it like in New York when one of their teams is doing what the Knicks are now?

Jeremy: It’s great to hear Dave talk about those teams and that era because they were electric! It was a decade where you felt like every time you walked into The Garden, something memorable was going to happen.  That Knicks locker room was Patrick (Ewing), (Anthony) Mason, (John) Starks, and (Charles) Oakley. It wasn’t just a team with persona, they had attitude!

It was so deeply meshed into the life of the city. New York is a baseball, football, hocky town, but basketball is different. When the Knicks are hot, there’s nothing else like it and it’s been a while.

Michael: This year, we’ll crown the seventh different NBA champion in seven years. From a business perspective, does this help the league? Does it hurt it because there is no “dynasty”?

Dave: I think it helps tremendously. If you asked me that question while I was CEO of The Garden, I would have said, “No we want to be a dynasty.” But this dreaded word, “parity,” some people hate. I don’t hate it at all. I think it’s really the best thing for the league.

These great, young teams in Oklahoma City, in Minnesota, in Indiana, coupled with some teams in really good teams in big markets, is very compelling.

Michael: Jeremy, from your time at ESPN, what makes live sports such a compelling platform to tell stories, shape narratives, and all those sorts of things?

Jeremy: There’s nothing else like live sports. In the age of the digital media universe, it’s more valuable and special than ever. We used to have other big tents in our cultural lives. Sitcoms, primetime dramas that everyone watched that would get 40 shares on a Thursday night. In this splintering, where everyone’s siloed and can watch whatever, whenever, the only thing that’s left is live sports.

I live in a world where I’m always talking about the biggest sporting events like the Olympics and World Cup. But these aren’t the biggest sporting events, it’s the biggest event! Super Bowl is not the biggest sports event on the American calendar; it’s the biggest event with the most eyeballs by far. It’s a national holiday. Sports is all that we have left that brings us all together.

Michael: Dave, how has the business of the NBA changed since your time with the Jazz and then Madison Square Garden?

Dave: What’s changed the most is how live sports drive the media. People keep saying, “This is a bubble that’s going to break. There’s no way these valuations will keep increasing.” But they do keep increasing because as media properties, they’re unparalleled. In the media world now, people aren’t going to cable. They’re streaming appointment programing and sports must be watched live.

For the NBA to sign a $78 billion deal for 11 years… When I came into the NBA, we signed television contracts for the entire league that were less than $10 million, and I’m not kidding.

Michael: Jeremy, from a journalist’s standpoint, when you think of business and sports colliding, how do you cover those stories?

Jeremy: The business of sports just keeps growing. It’s a bigger part of the story than ever before. When I was growing up, no one talked about how much money the team made. It wasn’t part of the discussion. But society today has become much more interested in general with dollar figures. So now, we discuss it in sports.

You just can’t disentangle business from sports now in a way that when I was a kid, it all felt removed from it.

Michael: Let’s end with a fun lightening round. Three quick questions, each NBA-centric. First, what was the first NBA game you ever attended?

Dave: I’m quite sure that it was a Lakers vs Celtics game in LA in the 80s when the firm I was at wanted to look into the Boston Celtics and they asked me to take a case team to look at the NBA. So, we set out to interview owners, coaches, and general managers to learn the business and really pull it apart.

The night before our meeting with Boston, I was in LA interviewing Dr. Jerry Buss, who became a great friend and mentor to me. We went to the game at the Forum and then got right on a red eye, walked off the plane and went straight to the office for a meeting. The guys were all saying, “Did you see the Celtics-LA game?” and we said, “Yeah, we were there.”

Michael: Favorite NBA player of all time?

Dave: Boy that’s a tough one for me. As a boy, watching the Knicks and Lakers in the NBA Finals, my favorite player was Dave DeBusschere. He was so strong, tough and to come to meet him and become friendly with him, Bill (Bradley), and Willis (Reed), it was like my dreams had come full circle.

Jeremy: I just loved Charles Oakley. He could be gruff at times, but underneath he was kind of a teddy bear. I love his game. I also loved watching Hakeem Olajuwon. He was just poetry in motion.

Michael: Last question, what are we going to see in the current NBA playoffs? Who advances? Who wins it all?

Dave: I’m going to say the Knicks are going to come back and win the series and go to the finals for the first time since ’99. I’m going to say OKC comes out of the West. My heart is with the Knicks. I would love to see them win a title.

Jeremy: As a New Yorker, I would love to see the Knicks advance, but it’s going to be tough to bet against the Pacers. I think Oklahoma City is the best team left standing, but that’s just me.

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