We're switching up the format again this week.

I've been teasing this one since Issue #17, and here it is: an entertainment attorney who represents both artists and athletes, on what NIL agents are actually charging, where the money in college sports is really coming from, and why the players cashing in hardest are the ones who were never going pro. Welcome back to The Closeout. Let's get into it.

A starter at a Power Four school could be making $2 million as a floor. St. John's might be paying its top player somewhere between $4 and $6 million, by Karl Fowlkes' estimate. Ohio State's football roster runs around $50 million. Fowlkes has spent almost 10 years as an entertainment attorney, most of it in music, and his read on the numbers is that college basketball money may already be bigger than music money.

The money showed up. I wanted to dig into what showed up with it.

I went into this conversation with a thesis I was fairly confident about. The music business spent 50 years learning what a bad contract costs, and I figured those same clauses were showing up for 19-year-olds in college sports. Fowlkes represents artists, songwriters, producers and athletes. He teaches at Rutgers Business School. If anyone could confirm it, he could.

He didn't.

"It's funny. Now I'm in it, I don't really think there's much crossover," he told me. "Everyone feels like the industries are much closer, but basketball, football, soccer, they're all their own worlds."

He has done this once already

Fowlkes grew up in South Jersey and has been based in Newark for the past 6 years. St. John's for undergrad, where he and I overlapped, then Villanova Law during the "Nova Knicks" title years. He started in corporate and financial law, staff attorney at a fintech startup, then Bloomberg. In 2018 he left to open his own practice.

The reason he opened the practice is what matters.

"When I got into the music business, I saw the songwriters and producers were being treated poorly," he said. "There was a real problem that needed to be solved. Producers and songwriters weren't adequately being paid."

He went where the problem was. The practice now represents artists, songwriters and producers, several of whom he calls household names, and it has been attached to deals that got covered on their own terms.

He teaches too. Management Skills at Rutgers Business School now, a music business course next semester. The model comes from his own time as a student, when an entertainment attorney taught a class or two a semester at Villanova and made the work feel real. Most courses run on what he calls an antiquated model, while the problems actually forming right now are the ones students could get out in front of.

He is a business operator himself. Consigliere, a wine bar in Newark he opened with his business partner, has been running for about a year and a half.

Then he moved into sports, for the same reason he moved into music. "On the college athletic side, it's the wild wild west with NIL. There's really not much regulation." The part that should worry anybody advising an 18-year-old: "I really wish I could say there was any regulation that will hold up in court. I'm not sure there really is."

So I stopped asking him about contracts and started asking about people. That's where the story actually lives.

The roles

In music, according to Fowlkes, the org chart is settled. The lawyer and the manager are the hub of the business. "Other than your content person, your music lawyer should be the first person on your team. They should be your hub of business, your connection point." Lawyer, manager, PR, agent. Everybody knows what they do.

In sports, he says the same chart doesn't exist. "There's not that many defined roles. There's a lot of loose parts, and they all sort of exist, but there's not the structure I like to see."

"Even if I'm dealing with an 18-year-old kid in music, I'm usually dealing with him and a manager. In sports, you almost have to talk to five people before you can talk to a person."

His term for it is AAU culture. A handler, an AAU coach, a high school coach, a cousin. "The 50,000 people around one person culture needs to be stripped away." He was careful about who he was describing. His issue is not that people are around these kids. It is that a lot of them have no track record. "There's been a lot of people involved, but a lot of them aren't really qualified. They don't have a track record of success in business. They're riding on this ticket. This is the guy who's taking us far."

When nobody's role is defined, nobody's job is to object. Fowlkes says NIL agents are taking 15% and up. Nothing on paper stops any of it.

What's actually being paid

Here is the part most coverage gets wrong, and Fowlkes was direct about it.

The large checks in college sports are not all endorsements. "This is not even an NIL endorsement deal. This is the school paying the kids." Athletic departments raise money internally and externally, pool it, and pay out of the pool. A player can sign for seven figures without a brand ever entering the room.

His test for a real NIL deal is a local car dealer. "If I'm the local Ford dealership and I give you a Ford and 100K, it's because there's some marketing value I get from this relationship. A lot of times it's not really like that."

That distinction changes who the athlete is negotiating against. A brand wants marketing value and will walk if the math is bad. A school wants to win games and is raising against donors. Those are different counterparties with different incentives, and most of the advice aimed at these kids is written for the first one.

Who is actually winning

Ask who benefits most from NIL and the obvious answer is the five-star recruit. Fowlkes says the obvious answer is wrong.

"The people who have benefited the most are the four-year guys who don't necessarily have the brightest pro futures. They might be a step slow for the NFL or the NBA, might be undersized, but they're a heck of a college player. Back in the day you have your All-American season, you might end up a seventh round pick, and you never hear from them again."

Now that player is clearing a million plus across a fourth and fifth year. The backup leaves with $400,000 and no student debt. Fowlkes framed that as a head start on a life that was always going to happen outside professional sports.

It also reframes the eligibility fight that blew up this year. The players who tried to get a year back after missing an NFL roster were not chasing a comeback. They were chasing a paycheck they could actually reach. "I wouldn't have done it, but I don't blame them for trying to get a bag."

On the NCAA's handling of it, he drew a line. "This is not an NIL issue. This is an NCAA issue and a timing issue." The NCAA adopted its new eligibility model after the 2025-26 season, and the transition rules gave another year to underclassmen while leaving out the players who had already used their final season. Those players had made decisions about their futures under the old rule. "That's an arbitrary rule that hasn't been collectively bargained." His read on what that produces: "It leaves a lot of lawyers like, okay, this is exciting, I might get a paycheck."

The successful model already exists

When I asked what good looks like, Fowlkes named three people: Russell Westbrook, Kevin Durant with Rich Kleiman, and LeBron James. Family offices. Defined seats. "You see these guys building family office style environments that are really what people should be replicating, even at a smaller level."

The Closeout has covered all three. Issue #17 had Westbrook taking a co-founder title and a board seat at Project B four weeks after retiring. Issue #16 had Durant's Thirty Five Ventures turning a $250,000 check into a reported nine-figure position.

Issue #19 had the version built for this exact problem. Jalen Brunson launched Thirty Third Management Group with his mother as president, his sister running client services, and a stated practice representing NIL talent. Fowlkes was at Villanova Law while Brunson was winning there. They both arrived at the same conclusion from opposite ends of the building.

The line

I asked Fowlkes what he wanted on the record. He came back to one thing, twice.

"Too many times the athlete does not feel like they are positioned to participate in their business conversations. Even if they're just a fly on the wall. Ask to be on the emails. You need that visibility."

Issue #13 had DeAndre Hopkins enrolling in finance classes at Clemson to understand the businesses he was investing in. Issue #16 had Harrison Barnes finishing a year of banking school before buying a bank. Both of them paid tuition, in money or in time, to get into a conversation that was already happening without them.

An 18-year-old signing for $2 million can skip that bill. The room is right there. They just need to ask to be put on the thread.

The full conversation is on YouTube, including Karl's take on the brown paper bag era of college recruiting and what he'd want in place before an 18-year-old signs anything. [Watch it here]

Coco Gauff, who has two Grand Slam singles titles at 22, joined World Team Tennis' Florida Flamingos as a player-owner ahead of the league's December relaunch, 52 years after Billie Jean King co-founded it.

Kurt Ainsworth, an Olympic gold medalist who pitched for the Giants and Orioles, bought back the bat company he co-founded for $225 million, three years after Fox Factory paid $572 million for it.

Young Thug, the Atlanta rapper, launched Primal, a holding company built to create, acquire and own intellectual property alongside artists, athletes and creators.

Travis Scott, the Houston rapper behind the Cactus Jack label, released his first Oakley collection as the brand's Chief Visionary Officer, three silhouettes he redesigned himself.

Taylor Townsend, who won the US Open doubles title this month, and NFL safety Kam Curl joined 40-plus creators putting nearly $1 million into beverage startup Sensori, taking equity and committing to activations rather than endorsement fees.

Karl's advice to any athlete was to get in the room and ask to be on the emails. What's the business advice you wish someone had given you at 22? Hit reply. See you next Wednesday.