🏀 Millions Left on the Table: NBA’s Costliest Endorsement Mistakes

Welcome to Buckets and Riches — where NBA stars don’t just shoot threes, they stack Gs. From tunnel fits worth mortgages to endorsement empires and crypto hiccups, we break down how basketball’s elite earn it, flex it, and sometimes… brick it. 🏀💸

The latest edition of our newsletter covers:

• Kyrie’s Painful Nike Breakup to Anta Rise

• Agent Zero’s $40M Flameout

• Haywood’s $10B What-If

💸Dropped and Rebuilt

Kyrie Irving’s Nike Deal Went Up in Flames After 9 Signature Shoes

Kyrie Irving’s line of signature shoes was perhaps Nike’s most popular, especially among younger hoopers. Launched in 2014, they weren’t priced in the $200 range like the LeBrons, Jordans, or even Kobes. They never even reached $150 like the KDs. Hovering around $110-130, Kyries became one of the most dominant brands in sneaker culture.

In September 2022, it was reported that WNBA players wore Kyries more than any other basketball shoes. Over 160 different players had worn them in the NBA before things went south.

Things went awry ahead of the release of the Kyrie Infinity, which was originally known as the Kyrie 8. In early December 2022, Nike and Kyrie parted ways, scrapping the release.

This came a month after the NBA and Nike suspended Kyrie after he shared a film on Twitter (now X) that contained antisemitic rhetoric. He initially refused to apologize for it.

Kyrie did eventually give in and said, “I initially reacted out of emotion to being unjustly labelled antisemitic, instead of focusing on the healing process of my Jewish brothers and sisters that were hurt from the hateful remarks made in the documentary.”

Nike, as a brand, usually distances itself from controversial figures. It took merely a month for the company to end ties with the 2016 champion.

Nike co-founder Phil Knight made it clear that he did not approve of anything Irving said at the time. “Kyrie stepped over the line. It’s that simple. He made a statement we can’t abide by.”

Nike had already finished their design for the Kyrie 8 and planned to release it. Kai didn’t appreciate how the company treated him. “I have nothing to do with the design or marketing of the upcoming Kyrie 8, IMO these are trash! I have absolutely nothing to do with them,” he said at the time. 

It didn’t take long for Irving to find a new home. Anta made him the Chief Creative Officer for their basketball division. Their KAI 1 sold out instantaneously. One launch at a Dallas store left 2,000 fans without a pair. StockX claimed that for every four KAI 1 pairs, three are sold.

“I've woven the essence of my heritage and my heart for basketball into the design of ANTA KAI 1. This is more than a shoe; it embodies our ancestors' strength and the future we're building,” said Kyrie at the time. Clearly, Irving has found peace when it comes to this sneaker debacle.

💸 Moneyball Moments

In 1996, Stephon Marbury signed a massive deal with AND1, but left to launch his own Starbury sneakers for just $15 a pair. The line had a strong cult following but collapsed when retailer Steve & Barry’s went bankrupt in 2009, leaving millions in lost potential earnings on the table.

💰Bag Fumbled

Gilbert Arenas Fumbled a $40 Million Deal With Adidas

Gilbert Arenas was a face of the Eastern Conference in the mid-2000s, averaging 25+ PPG in three consecutive seasons, and earning 3x All-Star and 3x All-NBA nods between 2004 and 2007. It was during this period that he became a top athlete for Adidas, changing their shoe game forever.

Set for negotiations over a deal with the brand, Arenas did the best he could to ramp up his popularity. He manufactured a grassroots movement and became the face of the Eastern Conference All-Star team. It paid off, with Adidas agreeing to a reported eight-year $40 million deal.

But in December 2009, things went horribly wrong. Arenas and Javaris Crittenton pulled guns on each other after a card game turned sour. Arenas admitted that while both he and Crittenton were losing money, he started "talking my good old s***." This riled up his teammate, and a war of words turned into the controversial locker room incident.

Arenas accepted a felony charge to avoid jail time, but it resulted in him losing the show deal he worked so hard to earn. Adidas cancelled the remainder of his $40 million contract in January 2010. Additionally, they removed all of Arenas' shoes and other merchandise from stores, cutting all ties with him.

Arenas was sentenced to two years' probation, 400 hours of community service, and a $5,000 fine. He was also suspended for the remainder of the 2009-2010 NBA season. After he returned, Arenas was never the same as a basketball player, with injuries taking a toll as well.

Arenas, however, has turned things around. He has become an immensely popular figure in the sports media world with his Gil's Arena podcast. He has also cleaned up his image.

Agent Zero managed to salvage his relationship with Adidas, which started retro-releasing his shoes in 2022. The original 'Gil Zero' shoe was rebranded as 'Agent Zero' and released in June 2022, starting a new chapter in Arenas' relationship with Adidas.

🏀 Gamble That Paid Dividends

Spencer Haywood’s Agent Destroyed His Billionaire Dreams

Spencer Haywood's career was expected to hit greatness given the way it began. He won Rookie of the Year and MVP awards in his first season (1969-70) for the Denver Rockets while they were in the ABA. Even after moving to the NBA in 1970 to play for Seattle, Haywood stayed a superstar in the making. 

Haywood also had an endorsement deal with a brand called Blue Ribbon Sports. In 1971, it changed its name to Nike. The power forward was at the peak of his prowess in the early 1970s, and the young brand sought Haywood to promote its products, including basketball shoes that were supposed to compete with Converse’s Chuck Taylors. 

Phil Knight sat down with the youngster and offered him two options: Either promote Nike for $100,000 or take 10% of the stake.

Haywood took the 10% stake in the company, but his agent wasn't happy. The agent ended up selling the stake for $100,000 and walked away with his $10,000. Haywood got only $90,000 from the deal. 

Today, Nike is valued at over $104 billion. If Haywood had kept his stake in the company, by today, he would have been worth an incredible $10.4 billion. The richest athlete on the planet by a mile and then some. 

Even if he had chosen to sell the stake in 2000, 25 years after getting it, he would have still made more than $2 billion and would have become the first billionaire athlete on the planet. Unfortunately for Haywood, his agent's desire to get his 10% cut cost him an unimaginable amount of money.

🏀 Shot Clock Back: NBA Stat of the Year

In 1994, the Denver Nuggets became the first No. 8 seed in NBA history to upset a No. 1 seed, beating the 63-win Seattle SuperSonics in the first round. Led by Dikembe Mutombo’s defense, Denver pulled off the 3–2 series win, punctuated by Mutombo’s iconic image lying on the floor clutching the ball.

📚Also Worth Reading

• Reports of Kawhi Leonard Forcing Raptors Owner for $15M Endorsements Surface After $28M Fraudulent Deal With Steve Ballmer

• “ICY HOT, Man Up”: Shaquille O’Neal Hyping Up His Endorsement While Reacting to Steph Curry’s Injury Has Fans in Splits

• Kawhi Leonard's $28M Endorsement Deal With Fraudulent Company Allegedly Linked to Steve Ballmer Circumventing Salary Cap