Sam Khan said something early in our conversation that I haven't stopped thinking about. He was explaining the transfer portal window to me — why kids can be changing teams while other teams are still playing — and he put it this way: imagine free agency happened before the Super Bowl. Regular season ends, playoffs begin, and the moment the first whistle blows in the wild card round, the league opens free agency. Players are signing with new teams while other players on other teams are still trying to win a championship.
That's college football right now. That's the portal.
I've watched this from the outside, and I'll be honest — I didn't fully understand the mechanics until Sam walked me through it. I understood the vibe. I understood that it felt chaotic, that coaches seemed frustrated, that my nephew Dylan Raiola just transferred to Oregon, that a kid at Cincinnati signed a deal worth roughly $5 million for a single season of play. I understood the numbers. I did not understand the structure underneath them, which is the thing that actually tells you whether this is fixable or whether college football has crossed a line it can't uncross.
The answer, after talking to Sam, is somewhere uncomfortable. The portal isn't broken. The system is just honest now — and honesty about what college football has always been is the thing nobody was ready for.
The academic calendar is doing work it was never built to do
The reason free agency happens during the playoffs in college football isn't that the NCAA is incompetent. It's that two systems are now running on top of each other and they don't share the same clock.
The academic calendar says: get your players enrolled before the spring semester starts, which is mid-January for most schools. The coaching staff says: I need my roster set before spring practice. The transfer portal says: you have this window, use it. And the postseason says: hold on, we're still playing until late January now, because the CFP expanded, because there's more money in a bigger bracket.
All four of those clocks are running simultaneously, and none of them were designed together. Sam put it plainly: "those two things just don't work together congruently, especially when the season extends as far as it does." He was talking about the academic calendar and the professionalized structure of the sport. They don't work together because one of them was never supposed to exist — the professional one. It existed, obviously, it's always existed, but it existed quietly, under the cover of amateurism, which the courts have now mostly stripped away.
What the portal does, structurally, is make visible what was always true: these players are labor. The window just tells you when labor moves.
The buyout is a contract. Act like it.
The Brennan Sorsby deal — Cincinnati quarterback, transfers to Texas Tech, reported $5 million for one season — is the number everyone focused on. I focused on it too, for about thirty seconds. The more interesting number is the one Sam mentioned after: the $1 million buyout triggered when Sorsby left Cincinnati.
That's a real contract structure. That's not a scholarship. That's not a handshake between a player and a program. That's a buyout clause, the same basic mechanism you'd find in an employment agreement, a business partnership, a coaching contract. Cincinnati essentially said: if you leave, you owe us. And the structure worked — not in this case, because Sorsby went anyway, but at Washington it worked. DeJuan Williams tried to enter the portal, looked at a buyout that would have required him to repay 100% of his deal, and came back to the Huskies.
Here's what I want people to sit with. A 20-year-old quarterback is now reading contract language with buyout provisions before he decides which program to play for. He may or may not have the legal representation to understand what he's signing. He almost certainly doesn't have the financial sophistication, at 20, to model out what a $1 million repayment obligation does to his life if the receiving program decides not to cover it.
I signed my first NFL contract in 2010. I was 23, I had an agent, I had a lawyer, and I still didn't fully understand what I'd signed until year two when I was sitting in a meeting and someone explained it back to me. These are college kids — some of them 18 or 19 — signing documents with six-figure and seven-figure consequences, during what is supposed to be an academic experience.
The buyout structure is correct as a mechanism. Players shouldn't be able to walk out on signed agreements without consequence — that's just how contracts work, and if you want players to be treated like professionals, they need to operate in professional structures. But the other side of that is: if you're going to hold them to professional contract standards, they need professional contract support. An 18-year-old at a mid-major who signs a deal with an ambiguous buyout clause and no lawyer reviewing it is not operating in a professional framework. He's operating in a professional framework on the liability side and an amateur framework on the support side.
That gap is where the harm is.
PULL QUOTE: "The courts have made it clear that trying to cap earnings on the players is not gonna fly." — Sam Khan
The programs that figured it out early are already pulling away
Sam made an observation about Oregon that I keep returning to: the funding matters, but it's not the whole story. "I give it not just credit to the funding, but also the strategy."
Oregon doesn't take 20 to 25 portal players a year. They take six to fifteen, and they target impact players at premium positions. They're not trying to rebuild through the portal — they're filling specific holes with specific people. That sounds obvious until you watch what other programs do, which is treat the portal like free agency in year one of a rebuild, bringing in volume and hoping it coheres.
The programs winning in this environment right now — Oregon, Miami, Indiana this year, Ohio State — are the ones that treat portal management the way a good NFL front office treats the waiver wire and free agency together. You know your roster. You know your needs. You make targeted moves. You don't overhaul.
Phil Knight built Oregon's foundation before NIL existed. The facilities, the brand, the recruiting infrastructure — all of that was in place when the money started flowing to players directly, which meant Oregon could redirect competitive advantage immediately. They didn't have to figure out how to build something from scratch while also navigating a new system. They just plugged players into an operation that was already running.
I think about this from an investment angle, because it's the same pattern. The companies that navigate a major market disruption best aren't usually the ones with the most cash. They're the ones that built operational infrastructure before the disruption hit, so when the rules changed, they weren't starting from zero. Oregon was positioned. A lot of other programs weren't. That gap compounds.
Free agency needs a commissioner
The cleanest moment of the conversation was when Sam described what college football actually needs: a centralized body, looking out for the greater good, with the authority to sequence everything the way the NFL sequences it. Season ends. Coaching changes happen. Portal opens. Draft happens. Spring practice. In that order. Not simultaneously.
The NFL took decades to build that structure. It wasn't gifted from the beginning — there was chaos, there were competing interests, there were owners who wanted one thing and markets that wanted another. What resolved it was a central authority with enough legitimacy and enough leverage to impose order on people who would not have chosen order themselves. A commissioner. A collective bargaining agreement. A shared financial interest in the product being good.
College football has conference commissioners who answer to their conferences. The SEC's needs and the Sun Belt's needs don't meet — Sam said it exactly like that — "they're not gonna meet." And they're paid not to meet. You can't get to a coordinated structure if every person with power in the room is paid to protect a subset of interests.
What I'd actually do, if anyone with real authority were asking:
- Pull the media rights into a single pool and negotiate them collectively. The NFL's power comes from the fact that every team is selling the same product together — not competing for individual deals. College football has conferences cutting their own deals, which means you're getting a fraction of the leverage you'd get if you went to market unified. Sam raised this point at the end of our conversation, and I think it's actually the key to everything else. Once the money is pooled, the incentive to cooperate increases. Once the incentive to cooperate increases, you can build the centralized structure. You can't do it the other way around — nobody voluntarily gives up control until they see a larger number in the alternative.
- Sequence the calendar and protect it with real enforcement. Portal window opens after the national championship game ends, stays open for a defined period, closes before spring semester starts. If the academic calendar and the playoff calendar are in conflict, one of them has to move — and since the playoff calendar is generating the revenue, the academic calendar adjusts, with appropriate protections built in. What can't happen is the current situation, where playoff teams play their last game and then their players enter a portal that's already half-empty because everyone else moved three weeks earlier. Miami and Indiana players got a five-day window after the rest of the country had already moved. That's not a competitive system. That's a penalty for winning.
- Require legal review before any NIL contract above a certain threshold is signed. I don't care what the number is — $50,000, $100,000, pick one. Above that number, an independent attorney reviews the contract on the player's behalf before it's executed. Not the program's attorney. Not the collective's attorney. Someone whose only client is that player. The buyout structure is correct. The information asymmetry inside it is not. You can have enforceable contracts and informed parties at the same time. That's not a radical ask. That's just how professional sports work.
Sam ended by saying the sport would benefit from "a centralized body that looks out for the greater good of everybody." I think he's right. I also think the people who would have to build it are exactly the people who benefit most from the current disorder, which is why it won't be built easily or quickly.
College football is the most popular sport in America that has never been organized on behalf of itself. It's always been organized on behalf of someone else — the universities, the conferences, the bowl committees, whoever was collecting at the gate. The players are the last people to get organized on their behalf. The portal is the chaotic, imperfect, court-forced version of that organizing happening in real time.
It's going to keep being messy until someone builds the structure. The sport is too big now to keep running on a calendar built for a different era.