Omri Casspi made $18 million playing basketball and now decides where $800 million goes. Russell Westbrook retired last month and took a co-founder title at a league that hands players equity. Von Miller wanted a jersey number and paid for it with a piece of his chicken company. Welcome back to The Closeout. Let's get into it.

Omri Casspi closed a $250 million third fund last week, taking Swish Ventures to roughly $800 million in assets under management. Sequoia Capital is in it, along with Israeli institutional investors, American university endowments and US institutions. He is the firm's sole managing partner.

Let’s go back to the start. Casspi went 23rd overall to Sacramento in 2009 as the first Israeli drafted into the NBA, played 10 seasons for seven teams, finished with Memphis in 2019, then played two more years at Maccabi Tel Aviv before retiring at 33. Career earnings: $18 million. Real money, and nowhere near the number that gets a retired player taken seriously as a fund manager.

He raised anyway. Sheva, his first fund, closed at $36 million in 2022. The first check went into Upwind Security at a $65 million valuation. Upwind raised $300 million this year at $3.8 billion.

The rest of the book looks like that. Swish has backed 21 companies and 9 are unicorns. Wonderful raised $550 million last week at $5 billion. Cognition, which he got into at $150 million in early 2024, is now raising at $47 billion. He told Calcalist his portfolio is worth close to $100 billion in aggregate.

The new fund will make about 12 investments at roughly $20 million each, in cybersecurity, infrastructure, physical AI, defense and government tech.

One thing to keep straight. The $800 million is money he manages for other people, and it counts paper gains on companies that haven't sold. If two of the big names correct, so does the number.

Issue #13 had DeAndre Hopkins taking finance classes at Clemson after handing money to businesses he didn't understand. Issue #16 had Harrison Barnes finishing a year of banking school before buying a bank. Casspi is the version of that story with a decade of results attached.

Sequoia wrote a check into a fund run by a guy who averaged 7.6 points a game.

Lando Norris co-founded LN4 Fusion, a junior racing team that bought AIX Racing's Formula 3 entry and is applying for an F2 spot. It runs Italian F4, Formula Regional European and F3 from next season, with René Rosin as team principal after 40 titles at Prema. Norris is separately paying out of pocket to fund young drivers who can't afford the junior ladder.

Chris Paul launched an athlete-led media company with Genius Sports and Connor Schell's Words + Pictures, contributing his own Ohh Dip!!! Entertainment. Schell produced The Last Dance and ESPN's 30 for 30 and will lead production. Genius Sports handles commercialization exclusively. First slate arrives in Q4 2026 with Paul hosting. No equity split disclosed.

Von Miller wanted the No. 40 jersey from Cowboys fullback Hunter Luepke and opened with an offer of free chicken for life. Luepke countered asking for 2% of Greener Pastures Chicken, which Miller said runs into the high hundreds of thousands. They settled at an undisclosed number. Luepke wears 30 now and owns part of a poultry company.

Russell Westbrook announced his retirement in August after 18 seasons, an MVP, two scoring titles, nine All-Star selections and 209 triple-doubles, more than anyone who has played the game. Four weeks later he had a new title.

He joined Project B as co-founder and chief strategy officer, with an ownership stake and a seat on the board. The league launches in January 2027 and will barnstorm cities across Europe, Asia and the Americas. It was started by Skype co-founder Geoff Prentice and former Facebook executive Grady Burnett, with former Hawks GM Landry Fields running men's basketball and former WNBA star Alana Beard as chief basketball officer. Steve Young, Candace Parker, Lauren Jackson, Cheryl Miller, Novak Djokovic and Sloane Stephens are all investors. Westbrook's stake was not disclosed.

Readers have seen both halves of this before. Issue #7 covered Westbrook as one of the athletes behind Oklahoma City's new soccer club and downtown stadium district, and the same issue's Deal Sheet had Azzi Fudd signing with Project B for equity rather than a paycheck. Issue #15 had Nneka Ogwumike leaving the WNBA for the same league, calling herself a partner and owner. Issue #16 had Unrivaled priced at $650 million with the players holding roughly 30%.

Fudd, Ogwumike, Alyssa Thomas, Jonquel Jones and Jewell Loyd have all committed, and the league says its women's salaries will beat what the WNBA pays. 

Westbrook's line about it was that “everyone should have a seat at the table.” He now gets to pull up his chair.

Travis Scott x Nike, Cactus Court. The Air Force 1 Low "Ice Blue" is his first AF1 in about three years, $120, style code JF7727-400, with ostrich-textured leather across the upper. Nike shock-dropped it August 31 at the Cactus Jack pop-up at 47 Chrystie Street in Chinatown, then released it wider on September 4 through cactusjack.com alongside the Zoom Vapor 12 HC at $170.

The collection was built around the US Open, and Carlos Alcaraz is credited as a collaborator on it. He wore the Vapor 12 in matches during the tournament and the AF1 away from the court, and Scott narrated the Nike campaign around his return from a four-month layoff.

A rapper put a tennis shoe on the defending champion and got his name on the design.

Complex ranked Fieg first on its 2026 Streetwear Power Ranking and ran a long conversation alongside it. The scale is the argument: more than 20 flagships, restaurants on two continents, a members-only padel and wellness club in the West Village, and a creative director title with the Knicks. He walks through how the campaigns get built, from Seinfeld to Scorsese to Messi, and spends real time on &Kin, the quieter sub-brand he started around Italian and Japanese fabrics. He also rejects the word streetwear outright.

The music business spent 50 years learning what a bad contract costs. Those same clauses are showing up in NIL deals right now, and I found someone who reads both. More on this soon. See you next Wednesday.