Happy Wednesday,
Justin Pugh spent 11 years in the NFL as an offensive lineman, got drafted by the New York Giants, and by the time his career ended, had already been building the next chapter. Today, he's the commissioner of the Italian Football League, working to plant the flag for American football in Europe, and he has a lot to say about why NFL players are their own worst financial enemy.
This week, Jake and I sat down with Justin to get into all of it.
It's hard to live off $100 million when you only get 40.
How They Got Here
Syracuse: Got a full scholarship, never had to think about paying for books. His words: "That's how crazy it is." It set up a pattern of not thinking about money that he'd spend his career trying to undo.
NFL Draft: Drafted by the New York Giants. Spent 11 years in the league, well above the average career of 3.5 years.
During his career: While still playing, worked for a family office doing ground-up multifamily real estate development. Got to learn the institutional investment space from the inside.
The honeymoon: Met a guy in Italy who played American football. Got handed a John Grisham book called Playing for Pizza. Went down a rabbit hole on NFL Europe and never came back up.
Post-career: Started researching what it would take to bring a pan-European football team to Milan. Realized the domestic Italian league needed to be built first. Got offered the commissioner role of the IFL (Italy's top American football division) and jumped at it.
The Big Idea: NFL Players Are Leaving Millions on the Table
This is the part of the conversation I kept thinking about long after we wrapped.
Justin's argument isn't that players are irresponsible. It's that the entire system is set up to make them fail financially before they even realize it's happening.
Here's how the math actually works:
A player signs what looks like a $100 million contract. By the time you subtract agent fees, advisor fees, manager fees, state taxes in places like California and New York, and the voided years baked into the deal, you're taking home closer to 40 cents on the dollar. But Adam Schefter tweets $100 million. The player thinks $100 million. And they spend it like $100 million.
Justin's fix isn't complicated. It's structural:
Switch pay periods from 36 weeks to 52; smaller, more frequent checks reduce the temptation to spend big
Report post-tax salaries publicly, not pre-tax; the number that gets tweeted should reflect reality
Make financial protections opt-out rather than opt-in; the 401 (k) used to be opt-in, and barely anyone enrolled. Now it's opt-out with a 2-to-1 match, and 99% of players are in
"If we just got really good at saving, it would do us so much more than if we ever got good at investing."
5 Tactical Takeaways
1. The number that gets announced is not the number you take home. A $100 million contract in a high-tax state with standard fees attached is closer to $40 million. The psychology of spending to the headline number is how players end up broke. Know your actual number.
2. Grow the pie before you fight over the slices. Justin's take on the 18th game debate: the right question isn't whether to play more games; it's whether more games grow total revenue enough to raise the salary cap. If it does, players win even if they trade one more game.
Current NFL revenue: $20-25 billion annually
Every international game packaged for streaming adds potential billions to the next media rights deal
More revenue = higher salary cap = more money for every player
3. Protect players from themselves with systems, not advice. Justin wants an AI-powered filter that automatically rejects bad investment pitches before they even reach a player's advisor. Not a "no guy" on the payroll, a no system baked into the process.
4. Build the infrastructure before the NFL arrives. Justin isn't trying to compete with the NFL in Europe. He's laying the tracks so that when the NFL wants Italy, there's already something there to absorb. His model:
Build youth academies in Italy starting at age 14
Pipeline Italian players to US colleges for NIL money and development
Create a pro league for players who want to come home
5. Steal great ideas from people ahead of you. Justin's blueprint for building his post-career portfolio came directly from watching veterans in the locker room:
Justin Tuck: got internships and mentorships on Tuesdays during the season
Larry Fitzgerald: spent every offseason in boardrooms with venture capitalists
Kelvin Beacham: started a fund while still playing
"I stole great ideas from players in the locker room that were doing things the right way."
Why It Matters
The thing that stood out most to me about Justin is that he understood something most players don't until it's too late: the game is rigged against you financially before you even cash your first check. The headlines, the taxes, the fees, the short career spans, none of it is designed to help you keep money. And by the time most guys figure that out, they're already out of the league.
What Justin did differently was simple. He paid attention to the guys who were doing it right while he was still in the building. That's it. He watched, he copied, he showed up.
The Italy thing is fascinating to me for a different reason. He could be building something that the NFL eventually absorbs into something much larger. He called it laying the tracks. I think about that a lot in the context of what the UFL is doing here in America, building the infrastructure and hoping the right entity eventually comes along and says, "We'll take it from here.”
If that happens for Justin in Italy, it becomes a very different story than commissioner of a small domestic league.
📩 And don’t forget: Bottom of the Ninth is back this Friday with the top three stories in sports and business from the week.
See you then,
Tyler & Jake