Hello football clan, a fresh week comes with a fresh set of stories about how money is shifting the market.

…if you haven’t yet.

In this newsletter we will cover:

1. Colts Owner Looked At Private Equity Investing

2. Caleb Williams Is Thinking Like an Owner Already

3. Jahmyr Gibbs’ Extension Set To Explode the RB Market

4. Does President Trump Signing the Executive Order Actually Change NIL?

5. How Kirk Cousins Keeps Getting Paid

💸 Money Trendzone

Indianapolis Colts owner Carlie Irsay-Gordon recently confirmed that the team has explored private equity investment.

They’re just not doing it right now.

That distinction matters.

Over the past year, NFL teams have gained the ability to sell minority stakes to private equity firms. Some have already done it. Others, like the Colts, are still on the sidelines—but clearly paying attention.

And the reasoning is pretty straightforward.

Irsay-Gordon pointed to stadium renovations as one example. Lucas Oil Stadium is approaching 20 years old, and upgrading a modern NFL venue isn’t cheap. Private equity gives teams another way to fund those kinds of projects without relying entirely on ownership cash or public funding.

That’s really what this comes down to: optionality.

Teams don’t need to sell equity. But having the ability to do it changes how they think about future spending. Whether it’s stadium upgrades, surrounding real estate, or other long-term projects, there’s now another funding route available.

That’s a major reason why publicly owned Green Bay Packers are at a disadvantage.

And even teams that aren’t interested today aren’t ruling it out completely.

Because once that option exists, it tends to stay on the table.

The takeaway:
Private equity isn’t something every team will use—but it’s quickly becoming part of how every team thinks about financing.

Enjoying the money side of football? We got something more for you.

WAG Life is a weekly newsletter that covers the lives of the women around it. Gossips, relationships, breakups, sideline fits we got it all covered.

📊 Beyond the Field

Caleb Williams is two seasons into his NFL career, and he’s already thinking about ownership.

Not endorsements. Not side income.
Ownership.

He launched an investment firm—888 Midas—right after being drafted in 2024, and the portfolio is already spread across:

• Women’s sports (NWSL, WNBA)

• Tech (including AI and robotics)

• Consumer brands (like Fruitist)

That mix isn’t random.

He describes it pretty simply:

“No vices… wellness, tech, and sports.”

So instead of chasing everything, the focus is narrow:

• Industries with long-term growth

• Areas where capital is already flowing

• And spaces where athletes increasingly have influence

One example—Fruitist.
Revenue reportedly grew from $50M to $400M over a few years while expanding globally. Williams’ firm holds equity.

He’s also been clear about the bigger picture.

Winning a Super Bowl is still the priority.
But long-term, he wants to own a team.

That part stands out more than the investments themselves.

Because it tells you how early the mindset is shifting:

• Not just earning during a career

• Not just saving after it

• But building toward ownership while still playing

And he’s not doing it alone.

The group around him includes people from real estate, private equity, and sports ownership—basically, operators who already understand how capital moves.

That matters more than the individual deals.

📌 The Bigger Picture

Jahmyr Gibbs is extension-eligible, and his next deal could end up resetting the running back market.

Through three seasons, the production is already there:

• Over 5,000 scrimmage yards

• Nearly 50 total touchdowns

• Consistent impact as both a runner and receiver

That last part is important.

Because the way teams value running backs has changed over the years. Pure runners don’t get paid like they used to. But players who can contribute in the passing game are starting to be viewed differently.

Gibbs fits into that second category.

Right now, the top of the market looks like this:

• Saquon Barkley → ~$20.6M per year

• Christian McCaffrey → ~$19M per year

• Derrick Henry → ~$15M per year

If Gibbs’ deal lands where it’s expected, it likely clears that range.

Something around $23–24M per year isn’t unrealistic, especially if teams start pricing him as more than just a running back.

That’s where this becomes bigger than one contract.

For the past few years, teams have been hesitant to invest heavily in running backs:

• Shorter career peaks

• Injury risk

• Replaceability

(Why Are Running Backs Paid So Less?↗)

But every so often, a player comes along who shifts that thinking slightly.

And this offseason, it’s not just Gibbs. Players like Bijan Robinson and De’Von Achane are also coming up.

So this might not be a one-off.

It might be the start of a small correction in how elite running backs are valued.

Not a full reset—but a move upward at the top end.

The takeaway:
The running back market isn’t coming back to what it was, but for the right players, teams are starting to pay up again.

🚀 NIL & The Future Pipeline

Donald Trump just signed another executive order aimed at college sports.

On paper, it tries to do a lot:

• Limit transfers (one free transfer as an undergrad)

• Cap eligibility at five years

• Restrict certain NIL structures like collectives

• And potentially penalize schools financially if they don’t comply

If you just look at the list, it feels like a reset.

But the more important question is whether any of it actually changes things.

Right now, probably not.

Executive orders can’t override existing laws or court rulings. And a lot of what this order is trying to address—NIL compensation, transfers, eligibility—has already been shaped by lawsuits and state laws over the past few years.

That’s why college sports looks the way it does today:

• Athletes can move more freely

• Money is flowing through multiple channels

• And the NCAA doesn’t fully control the system anymore

This order runs into all of that.

Even the timeline reflects it. The proposed changes wouldn’t kick in until August, and there’s a strong chance parts of it get challenged in court before then.

So if it’s unlikely to hold as-is, why do it?

Because this isn’t really the end solution. It’s pressure.

For years, college sports leaders have been asking for a federal law to create a single framework, something that overrides state-by-state rules and gives the NCAA clearer authority again.

That hasn’t happened.

This order is another attempt to push that conversation forward, especially with things like the SCORE Act still stuck in Congress.

In the meantime, the system keeps evolving anyway.

Schools are already moving toward direct revenue-sharing with athletes. NIL collectives are fading in some places and being replaced by new structures. And athletes have more leverage than they’ve ever had.

So even if parts of this order stick, it’s unlikely to fully reset the system.

It’s just another step in a much longer process.

College sports isn’t being reshaped by one rule change, it’s being pulled in different directions by courts, lawmakers, and money, all at the same time.

The 🧢 Space

Kirk Cousins is now one of the highest-earning players in NFL history, with over $340M in career earnings, that’s more than Tom Brady’s. And it puts him alongside names like Aaron Rodgers and Matthew Stafford, even though his on-field résumé looks very different.

(What Does This Deal Mean For Fernando Mendoza?↗)

The interesting part isn’t the total, it’s how he got there.

Early in his career, Cousins didn’t lock himself into a long-term deal with Washington. Instead, he played on back-to-back franchise tags in 2016 and 2017. That’s usually a risky path. One injury or one bad season can cost a player everything. But in his case, it gave him short-term money and, more importantly, leverage.

When he hit free agency in 2018, he used that leverage to sign a fully guaranteed three-year, $84M deal with Minnesota. At the time, that kind of structure wasn’t common for quarterbacks. Teams were willing to pay, but not necessarily guarantee everything. Cousins pushed that line.

From there, the pattern stayed the same. Extensions in Minnesota, a deal in Atlanta, and now his latest situation with the Raiders, all built around guarantees. He’s now heading into his 11th straight season where his contract is fully guaranteed in some form, and roughly 99% of his career earnings have been locked in.

What makes this stand out is the contrast. Cousins has had a solid career—Pro Bowls, consistent numbers, a long run as a starter—but not the kind of postseason success you usually associate with players at the very top of the earnings list.

A few years ago, that might have limited what he could demand. Now it doesn’t.

The market has shifted. Quarterbacks have more leverage, and guarantees are becoming more normal at the top end. Cousins wasn’t the only reason that changed, but he was one of the first players to consistently push for that structure and actually get it.

And over time, that approach compounded.

Now he knows he has leverage to make more as a veteran who is ready to pass on the knowledge, and at the same time be a reliable prospect behind the center.

Things are starting to heat up so stay tuned and wait for our issue next week for more interesting stories like this.

This is a two-way conversation so don’t forget to reply to this email with a feedback, we go through all our replies.

And do refer us to a friend you would want to make a part of this conversation.

See you soon!