David Falk on Michael Jordan, Space Jam, and the Business of Sports & Wine

In this episode of Uncorked: Wine – Business – Life, we sit down with one of the most influential sports agents of all time—David Falk. Known for representing Michael Jordan and shaping the modern sports marketing industry, Falk has negotiated some of the most groundbreaking deals in history, including the creation of the Air Jordan brand.

Introduction to a Legend

Welcome to Uncorked Wine, Business and Life with Bill Green. I’m Gerald Colton, along with Bill Green, and we have an extremely special guest here today. He is known as the greatest sports agent of all time, a true legend who has done so much more: David Falk.

Welcome, David. We are in Bill’s lovely house here in Boca Raton. David, thank you so much for being here. You and I have spent a little bit of time together on the golf course. I think you were with me the first time I played Pine Hill Golf Club and almost killed Lee Trevino. David is an avid golfer, but his story is much deeper. He is a lawyer who decided he had a much bigger fish to fry.

Early Life and Foundations

I grew up in a very working-class neighborhood in Seaford, Long Island. My mother, Pearl Falk, was very highly educated. she was a teacher with two master's degrees and served as an interpreter in Washington, D.C., for Nelson Rockefeller during World War II. My dad was a butcher who never finished high school. It was a real oil-and-water marriage, but my mom was my lifetime mentor.

I always wanted to be a lawyer. Some kids want to be astronauts or basketball players, but I always had that goal. When I got to Syracuse, I had the two star freshman players on my floor. We became great friends. For the last 55 years, I’ve had this romantic notion that when we became seniors and they got drafted, I would represent them.

Entering the Sports Representation Business

By the time I was a senior, I realized I didn't have a clue what I needed to do, so I went to law school. This was 1973, and the business was literally just starting. Mark McCormick in Cleveland basically invented the business. He is the godfather of sports representation. Most people in it were sole practitioners like Larry Fleischer or Bob Wolf.

I was in Washington and heard about Donald Dell. He was a tennis guy. I called him for months, but he was always in meetings or on vacation. One day, I made a rare visit to the law library. Back then, they had payphones. Every ten minutes, I put a quarter in and called him. After my seventeenth call, his secretary ran out of excuses. He finally gave me an interview.

I came to his office at noon, and he kept me waiting three and a half hours in the lobby. When he finally called me in, he told me they weren't hiring people with my credentials. I told him I would work for free. I started that summer after my second year of law school while also working full-time for a large Chicago law firm called Sidley Austin.

I got married a week later to Rhonda. She’s the best; she should get the Nobel Prize for being married to me for 50 years. I started for free, and seventeen years later, it didn't get much better than that, but I loved what I did.

Recruiting and the Collegiate Pipeline

At the height of my career, prior to the rookie wage scale in 1995, the top coaches in the country were very hands-on. That included Dean Smith at Carolina, Coach K at Duke, John Thompson at Georgetown, Bobby Knight, and Rick Pitino. They told us "no recruiting." Dean Smith would say if you even bumped into Michael Jordan’s mother at the food line, you were off the list. You had one hour when school ended to make a presentation.

When I got to the firm, which became known as ProServ, they represented Carolina players like Dennis Wuycik, George Karl, and Bobby Jones. Later came Tommy LaGarde, Phil Ford, Dudley Bradley, Mike O'Koren, Al Wood, and James Worthy. When Michael Jordan came out in 1984, we had represented almost all the players from that program.

Coach Smith was an aristocrat. He made Donald Dell come to the meetings even though I ran basketball. John Thompson was the opposite; he didn't want Donald there at all. The players knew Donald would do the first contract and then become "the Ghost." I was the young bald guy who would actually be there. I think because Michael's dad was bald, he felt a comfort level.

The Importance of Honesty in Agent Relations

Most agents lie to players. They tell a guy he’ll go number one when he’s really going fifteen. I met Scotty Thurman’s parents after Arkansas won the national championship. I told them he shouldn't come out because he wouldn't go in the first round. Another agent told them he’d go at twenty. Scotty didn't get drafted at all. It makes you want to cry because you try to tell them the truth while everyone else is stroking them.

That truth-telling is what made the difference. I wrote a book called The Bald Truth because you might not like what I say, but it is the truth. That is the credibility I built with Michael Jordan, Patrick Ewing, and Dikembe Mutombo. If you start a relationship on a lie, they won't trust you when something big comes up down the road.

Strategic Negotiation and Market Control

In 1993, we met Chris Webber. Everyone said he wanted to hire someone of color. I had Fred Whitfield working for me, but I intentionally did not bring him. We had also signed Sean Bradley, the number two pick. We never actually met Sean Bradley before signing him; he was on a religious mission for the Mormon Church in Australia. All ten NBA owners recommended me to his mission leader.

Other agents told Chris Webber’s parents not to hire me because I represented Sean Bradley. I told them that if the top five players understood the business, they would all pick the same agent to control the market, much like the Fab Five did at Michigan. I told them, "When your son goes number one and Sean Bradley goes number two, and I get Bradley more money at number two than Chris gets at number one, you’ll know these other guys lied to you."

Chris went one, Sean went two. I signed the deal for Sean Bradley first—$44 million for seven years. Chris and Penny Hardaway combined did not make what Sean made in those first years. The following spring, Chris’s dad, Mayce, told me he thought I was the most arrogant person he’d ever met, but everything I said was true.

I had a similar situation with Desmond Howard. His advisor went to the pro teams in Cleveland, and they all recommended me. I told Desmond he wouldn't go number one. Only three wide receivers have ever gone number one, and they were much taller than him. I told him he’d go four to six. He didn't pick us; he picked Lee Steinberg, who told him he'd go number one. He went number five to the Redskins.

We eventually did his marketing, but the contract holdout destroyed his image. The fans were upset that a rookie thought he could supplant three All-Pro wide receivers. We lost a great player because we were honest, but I can't lie. You'll never have a long-term relationship if you lie about something as silly as the draft.

A Shared Appreciation for Fine Wine

David and I have a relationship because of an amazing affinity for wine. Looking at the glass next to you, tell me the "bald truth." I would say this is a great everyday wine. It doesn't have the depth of an Amarone or a big Cab, but you don't always want a big wine. I drink red wine almost all the time. This is light, has a nice flavor, and is clearly a young wine.

That is a Saddle Hill 2022, my new winery. It’s a Bordeaux blend. Now, I want you to taste this next one. I’m not going to tell you what it is yet. This has a great nose. That is a ten. It is a 2009 Screaming Eagle. I picked this because that night in D.C., when we went to a restaurant, Bill brought a 2010 Screaming Eagle. That was my first restaurant investment.

The owner of a place called Trigara told me the sous chef at Galileo's was opening a restaurant and asked if I wanted to invest. I was in it for 18 years and made a good return. It was a great experience. Regarding the wine, there is such a snob appeal for French wines. I think if I gave you a glass of this versus a Harlan, a Grace Family, or Bryant Family, very few people could taste the difference.

If you can’t hear the difference between a $5,000 speaker and a $500,000 speaker, why spend the money? For people who don't drink a lot of wine, Turley Zinfandel is a great value. I love the Dusi, the Dogtown, and the Pesenti. Sometimes people taste "oak" in over-aged barrels and think it's amazing, but often that's because there is no fruit left.

Before we sign off, I have to tell a story. I was on the board of a startup liquor company. A friend named Jeff had a family business called American Scones that supplied Starbucks. He decided to start a liquor company focused on flavor-infused vodkas. By a fluke, Baron Eric Rothschild was trying to make a black vodka called Blavod.

I took my daughter Dana to Europe, and we visited Lafite. I was shocked to see bottles going back to the 1700s. In 2003, they had the 2000 vintage in a vat. He gave us a glass with a ladle. I thought my wife was going to dive in. That, along with a '61 Latour, was the best wine I’ve ever had.

Representing Michael Jordan

Michael Jordan has been an amazing friend. When I started representing him at age 33, I was nervous that if I got too close socially, he wouldn't respect my advice. I kept a distance. When he had to choose Nike, he didn't even want to visit them. George Raveling and Sonny Vaccaro were influential, but I was the one who insisted Nike would be the most aggressive in marketing him.

I had to tell him things he didn't want to hear. He learned I would be brutally honest. I started with him in 1984, went on my own in 1992, and he stayed with me through every business sale. He could have gone to a huge firm like Sidley Austin or started his own agency like LeBron, but he stayed.

Jordan’s Competitiveness and Work Ethic

There will never be another Michael. He came from a loving, two-parent family that did not coddle him. They pushed him to grow. At Carolina, he played for Dean Smith alongside James Worthy and Sam Perkins. He learned how to play with other great players and willed himself to be great.

Coach Smith told Michael after his sophomore year that he was the best offensive player in the country but not the best defensive player. He stayed another year to learn defense and became arguably the second-best defensive player in history after Bill Russell.

He was incredibly competitive. During an All-Star game in Charlotte, my colleague Jeff Wexler wouldn't stop talking about his client, Glen Rice. Michael eventually got annoyed and left. The next day, Glen Rice set a scoring record in the All-Star game. The first game after the break was Charlotte at Chicago.

Michael decided to guard Glen Rice himself. Glen was averaging 24 points a game. That night, he took 15 shots and I think he had zero. After the game, Glen told Jeff, "I don't know what you said to him, but it was like putting a red flag in front of a bull. If you ever mention my name to Michael Jordan again, you're fired."

The Success of Space Jam

I’ve seen the movie Space Jam a hundred times because of my son. Ken Ross worked for CBS and we decided to make a video for Michael around '86. Gary Bettman, who was then with the NBA, had a joint venture with CBS and Fox. I told Gary I wanted a $600,000 guarantee for Michael.

Gary asked if I woke up deciding to be an asshole or if it came naturally. He said Magic Johnson’s video only sold 50,000 copies, and I was asking for a 200,000-copy guarantee. We eventually settled on a $300,000 guarantee and a 50% royalty. We sold over four million copies.

We got movie offers, and I teased Michael, telling him he couldn't act and could only play himself. We saw the Hare Jordan commercial with the Looney Tunes and loved it. Warner Brothers was the most motivated to make the movie. Bob Daly was dating Carol Bayer Sager, and she really pushed for the project after Michael was kind to her son.

I didn't know anything about making movies. Bob Daly and Terry Semel held my hand through the process. We chose Joe Pytka to direct because Michael was comfortable with him. The producer, Ivan Reitman, was a big-time Hollywood guy and was very snobby about Joe being a "commercial guy."

They clashed. Joe told me he was going to strangle Ivan. I told Ivan that in sports, great players don't always make great coaches because they expect players to do things they aren't capable of. I was hinting that Joe was the right coach for Michael. When the credits came on and it said "A Falk-Ross Production," I got a real kick out of it.

Legacy, Education, and the Wage Scale

David turned this into a business more than anyone else. Most agents back then were just lawyers who wanted to be near sports, but David was a visionary. Keeping Michael Jordan was the real talent. Everyone would have worked for Jordan for free, but David kept his trust by telling him the truth.

The biggest influence in my life was my mother. In 1998, on the anniversary of her death, I made a modest gift to Syracuse for a scholarship. Later that year, I sold my business, and the university asked if I wanted to reconsider the gift. I ended up starting the David Falk School of Sports Management.

I look at myself as a teacher. The rookie wage scale today homogenizes talent. If Warren Buffett were an NBA agent, they’d pass a rule saying he could only get an 8% return. I thought the wage scale was the dumbest thing ever. It started because the veterans were upset that rookies were making so much.

Magic Johnson’s 25-year deal was actually poor because it was based on deferred compensation during high inflation. Patrick Ewing’s rookie deal was for $3.2 million a year, which was more than Magic was actually taking home. The veterans were mad, but the rookies were the ones setting the market.

The Value of Superstars

I focused on the economic impact of a player. Nike needed Michael Jordan more than they needed anyone else. I developed the "Fame mini-market." I told the union that if you cap rookies, you just give the teams leverage to underpay superstars. I hate max contracts because they overpay the second-tier players.

If you have a $4 billion pot to spend, do you want to spend it on Screaming Eagle or on 400 cases of $10 wine? When you cap the stars, you overpay the middle. In the movie business, Denzel Washington makes $40 million because he is the star. An extra makes scale. If the extra complains, you tell them to go back to being a busboy.

There are maybe eight true superstars in the NBA who bring in the fans and the TV deals. I would pay Steph Curry $200 million a year so I wouldn't have to pay a mid-tier player $30 million. The superstars move the needle in every category, from attendance to merchandise.

My friend Bruce Levinson bought the Atlanta Hawks and asked for my advice. I told him there are two classes of players: guys you can live without and guys you can't. Pay whatever it takes for the ones you can't live without. For the others, if you can't get them for what they're worth, there are 50 guys just like them.

In 1996, Shaquille O'Neal became a free agent in Orlando. I told them to pay him $20 million even if they thought he was worth $15 million. I told them Shaq is the Hope Diamond; the extra $5 million is the insurance. They offered him $15 million, and he went to the Lakers.

Conclusion: Teaching the Business

If you ask Michael Jordan what the most important thing I did for him was, he wouldn't say it was the money or Space Jam. He would say I taught him the business. As the son of a teacher, that is the highest compliment. I tell these stories to teach lessons about practice, not just theory.

When I put my "uniform" on—which used to be a suit—I was very intense. I had a job to do. Representing Michael and Patrick in my 30s, I felt a self-induced pressure to perform at an A-plus level. It’s about confidence. Never let them see you sweat. Now, the glass is half full, and we’re moving on to the next episode. Thank you.