Jerry Jones bought the Dallas Cowboys for $140 million in 1989.
Danny brought that up during our kickoff conversation — he'd been watching the Cowboys documentary — and the number just sat there for a second. $140 million. Roughly $370 million in today's dollars, which sounds like a lot until you understand that the Commanders just sold for $6 billion. That the Cowboys themselves are probably sitting at $10, $11 billion. That Jerry bought the most valuable sports franchise in the world for the price of a mid-tier luxury apartment building in Manhattan, adjusted for time.
The thing about that number isn't the discount. The thing is why the discount was even possible. Nobody in 1989 understood what the TV deals were about to do. Nobody saw that the rights money would compound into something that made every other lever in professional sports — ticket sales, merchandise, stadium naming rights — feel like rounding errors. The money followed the eyeballs. Jerry just happened to buy before everyone else figured out where the eyeballs were going.
That's the entire episode, even though neither of us said it that cleanly. Everything we talked about — the salary cap rising $23 million year-over-year, the CBA negotiation in 2030, the NIL chaos in college sports, the NWSL — it all comes back to one question: who controls the eyeballs, and is the money following yet?
The cap is a symptom, not the story
The salary cap went from $255 million to $279 million this season. Danny asked me whether that was significant, and I gave him the technical answer — yes, every team has to spend somewhere between 85 and 90% of it, the top 20 or 22 guys are getting the bulk, everyone else is on or near minimum. That's all true.
But the more interesting answer is why it went up. The cap rises because revenue rises. Revenue rises because TV deals get renegotiated larger. TV deals get larger because the NFL is the one thing left that makes people watch something live, together, at scale — and advertisers will pay enormous premiums for that. The cap number is a downstream output of a media rights machine that most players never think about when they're looking at their contract.
I mentioned on the show that 2020 was the one year in recent memory where the cap actually went down. The pandemic. Revenue reversed, the cap reversed, and teams that were built around certain financial assumptions suddenly had to make cuts at the edges of their roster. The guy on the back end of your 53-man roster — the one who might be a special teams ace or a developmental piece — he was the one who got squeezed. Not because he did anything wrong. Because the TV money that season wasn't what anyone projected.
Most players understand their contract. Very few understand that their contract is set inside a system whose ceiling is determined by media executives and league TV negotiators who operate in a different world entirely. You want to know what your second contract is going to look like? Watch what the broadcast deals do between now and then. That's the real indicator.
Jerry bought before anyone knew what they were buying
The Cowboys documentary has me thinking about timing in a way I don't usually sit with. $140 million for a franchise that is now the most valuable sports property on the planet. The math on that return is almost too large to process. And the reason it happened — the reason that was available to him — is that the NFL's relationship with television was still being figured out in real time.
The owners in 1989 knew football was popular. They didn't know it was about to become the one thing cable, then satellite, then streaming would organize itself around. That gap between popular and structurally essential to the entire media ecosystem is where Jerry made his money.
I think about that a lot when I'm looking at investment opportunities. Not just in sports. The question isn't whether something is good or valuable right now. The question is whether the money that will eventually reflect its value has started flowing yet. If it has, you're probably late. If it hasn't, you have to be honest about why it hasn't — whether it's because the world genuinely hasn't caught up, or because there's a real reason the money isn't following.
The NWSL is where I think the gap still exists
I went to a Gotham FC game recently. Hung around after. Watched players signing autographs, saw the media presence, felt the energy. These are real fans. This is a real product. And the infrastructure around it — relative to what these athletes can actually do on the field — is still nowhere close to matching.
Danny asked me what league has the kind of growth potential the NFL had 30 or 40 years ago. I said NWSL, and I meant it. The Portland Thorns are a useful example. They've won championships with resources that would be considered embarrassing in any equivalent men's league. They built a winning culture in spite of the investment, not because of it. The question I keep asking is: what do they look like with half the resources of an NFL franchise? Not the same. Something different entirely.
The WNBA is moving fast — the New York Liberty are at $450 million in valuation, which felt impossible five years ago. But the NWSL feels like it's still in that pre-caught-up zone. The loyal fan base is already there. The competitive product is already there. The TV deals and the sponsorship infrastructure are still catching up to the reality of what the fans are already doing on their own.
I may have already missed the cheapest entry point. But the window where the money hasn't fully followed the eyeballs — I don't think that's closed yet.
PULL QUOTE: "If you can find the Dallas Cowboys of the late '80s, early '90s — when Jerry bought the team — that's the bet." — Ndamukong Suh
The CBA negotiation nobody is preparing for
The current CBA runs through 2030. That sounds far away. It isn't. And the players who are going to be at the table for that negotiation — or whose careers will be shaped by it — are already in the league right now, most of them not thinking about it at all.
Here's what I told Danny, and what I'd say to any player who'll listen: the leverage in that negotiation is going to be built or surrendered over the next five years based on how well the NFLPA understands the media rights landscape. The ESPN deal, the Netflix deal, the broadcast packages that are getting carved up and re-priced right now — those revenues are what set the cap ceiling. The players' share of those revenues is what gets negotiated. If you don't understand where the money is coming from, you cannot negotiate intelligently for how much of it you deserve.
The pandemic year taught us what happens when that revenue reverses. The cap went down. Players lost money they didn't know they were counting on. The more important lesson is that the players who understood the revenue structure — who knew why the cap was going down and by how much and for how long — were positioned to make smarter decisions about their contracts in that window. The ones who didn't were just hoping their agent had it figured out.
College football has a version of this problem coming too, and it's messier. There's no CBA. NIL is a patchwork. The Big Ten and SEC are consolidating power and TV dollars in a way that's going to make the have/have-not gap in college sports look completely different in ten years. UCLA flying to Nebraska for a conference game isn't just a logistics headache — it's a symptom of a system reorganizing itself around television revenue in real time, without any collective structure to ensure the athletes see an appropriate share of what they're generating.
What I'd actually do with this, if I were advising a player today
Three things, in order:
- Understand what sets your contract ceiling before you negotiate your contract. The salary cap number for your contract year isn't arbitrary. It's the downstream output of broadcast rights, revenue sharing, and CBA terms that were negotiated years before your agent sat down across from a GM. If you know the cap is on an upward trajectory because of a new ESPN deal — the way it is right now — that's negotiating information. If you know a pandemic-style revenue disruption is coming, that's also negotiating information. Most players walk into second-contract negotiations knowing their own stats and their market comparables. Almost none of them know the macro revenue picture that will determine whether the GM has room to pay them or is already squeezed. That information is not secret. It is just not studied.
- Think about ownership earlier than feels relevant. Jerry's $140 million became $10 billion because he bought before the TV money clarified. The version of that trade that's still available — in women's sports, in emerging leagues, in international markets — requires exactly the same kind of move: buying before the money fully follows the eyeballs. I'm not saying every player should be buying sports franchises. I'm saying the mental model matters. The question where are the eyeballs going and has the money caught up yet is useful in every investment context, not just sports. The players I've watched build real wealth after football are the ones who learned to ask that question early, about multiple asset classes, before everyone else in the room had already asked it.
- Take the 2030 CBA seriously right now. The NFLPA needs players who understand the business well enough to negotiate it. That doesn't happen in the room in 2030. It happens in the years before, when players are building financial literacy, asking hard questions about revenue structures, and demanding transparency from the league about where the money comes from. The players who benefit most from that negotiation will be the ones who treated the CBA as a live issue, not a future problem. The ones who hand it off entirely will get whatever the informed ones negotiated for them — which is usually less than they deserved.
Danny's Super Bowl pick was the Ravens. I respect it. Lamar's too good, the defense is built, Justin Madubike is a guy I have a lot of respect for — but they've been close before without getting over. The season will tell us what it wants to tell us.
What the season won't tell you — what it never does — is where the real money is moving. That part you have to figure out yourself, before the cameras show up.