Joe Pompliano

A professional sports gambler used analytics to turn a $700,000 loan into more than $300 million. This is the wild story 👇👇👇

@jasonrmcintyre The flip side is that 70-80% of the athletes never have to pay back the money. It’s the VC model. The home runs pay for the rest (and then some).

@JoePompliano I kind of hate this Predatory money advance and then demand a king’s ransom when they make it? That’s dirty Wonder if all those guys read their contracts (I’m assume they were teenagers from impoverished backgrounds)

Fernando Tatis Jr. has lost his lawsuit against Big League Advance. Tatis was paid $2 million as a minor leaguer in exchange for 10% of his future earnings. This was not a loan. If Tatis didn't make it to the big leagues, he didn't have to repay the $2 million. But Tatis did make it to the big leagues and later signed a 14-year, $340 million contract. That meant Tatis owed Big League Advance $34 million. Tatis had publicly praised Big League Advance, saying the $2 million allowed him to hire a personal trainer, upgrade his apartment, and eat better food. But after realizing he owed $34 million in exchange for $2 million, Tatis sued the company, alleging that they used predatory tactics to lure him into an investment deal that was really an illegal loan. The judge disagreed. The agreement was upheld this week and Tatis was even ordered to pay Big League Advance’s legal fees. This is a big deal because Big League Advance has signed deals with 700+ athletes, including Elly De La Cruz (MLB) and Nolan Smith (NFL), across MLB, NFL, and college sports (think: NIL). And now that the courts have ordered Fernando Tatis Jr. to follow through on the agreement, other potential legal challenges will likely go the same way.

P.S. if you enjoy learning about the business and money behind sports, join 135,000 others who read my 3x weekly newsletter. Link: huddleup.substack.com

Indianapolis Motor Speedway is so big that it could fit: • Churchill Downs • Yankee Stadium • Rose Bowl • Taj Mahal • The White House • Liberty Island • Roman Colosseum • Vatican City And at 300,000+ people, the Indy 500 is the world's biggest single-day sporting event.

@LeDuffsCadillac They don't remove the ice in season. The basketball court is built on top of it.

@JoePompliano Dude. Pistons and Red Wings play in the same building a couple days apart last week. Hardwood to ice back to hardwood in 4 days

Now I want to see how they bring the ice back when the season begins

The Enhanced Games have arrived. Athletes are allowed to use steroids, HGH, and other performance-enhancing drugs, and if they break a world record, they get $1 million. It's a crazy concept (and the business model behind it is fascinating). READ MORE: huddleup.substack.com/p/the-enhanced…

@stacker_sports Looks like there were a lot of decals in the video above

@JoePompliano They flood it, freeze it and then paint the lines. Pretty straightforward.

This is a crazy experiment. Wild times.

The Enhanced Games recently released substance usage data from its clinical trial: • 91% of athletes used testosterone • 79% used HGH • 62% used stimulants (Adderall) • 50% used metabolic modulators • 41% used EPO • 29% used anabolic steroids READ: huddleup.substack.com/p/the-enhanced…

The balls at this year's World Cup need to be charged before each match and feature special sensors that collect spatial positioning data in real-time.

Apple TV just announced that (for the first time ever) this weekend's LA Galaxy vs. Houston Dynamo match will be shot entirely on an iPhone 17 Pro. Here's what the setup looked like last year when they began testing it during MLB games.

@ruairiSpain @GolfDigest He says later in the video that his caddie gets base pay and then 7-8% of prize money (10% for wins).

@JoePompliano @GolfDigest I thought caddies get 10% of winnings The numbers don't add up. All his expenses add uo to 10% Someone help me with the math!

Ben Griffin says he spent about $50,000 per week last year on travel, housing, coaches, trainers, etc. If you multiply that by the 30 events he played in 2025, that's $1.5 million in expenses against roughly $15 million in on-course earnings. (h/t @GolfDigest)

I recently wrote a 3,000-word piece breaking down Kroenke's sports strategy. The TLDR is that Kroenke buys land in high-growth areas → Uses a sports team as the "anchor tenant" → Builds commercial development around it → Monetizes the entire ecosystem (rents, naming rights, adjacent real estate). You can read more here: huddleup.substack.com/p/silent-stan-…

Stan Kroenke is on a generational run right now. In the last five years, his teams have won the... • Super Bowl (LA Rams) • NBA Finals (Denver Nuggets) • Stanley Cup (Colorado Avalanche) • Premier League (Arsenal) He also owns SoFi Stadium, which has hosted the Super Bowl, the CFP National Championship Game, upcoming World Cup matches, and the 2028 Olympics opening/closing ceremony. Not to mention, Kroenke also recently became the largest private landowner in the United States, with 2.7 million acres. That's roughly the combined size of Chicago, Houston, Phoenix, Philadelphia, and San Antonio.

I’ve seen a lot of bad takes about the Audemars Piguet x Swatch collab so I wrote about why AP is actually doing it. The strategy has nothing to do with making a quick buck or its trademark losses in the U.S./Japan. Read: huddleup.substack.com/p/did-audemars…

People have lost their minds

Rory is showing Brooks his Omega De Ville Tourbillon that he bought after winning the 2019 FedEx Cup. Omega only produces about 20 of these watches every year and they retail for around $250,000. (h/t @garystriewski)