What happens when a basketball legend’s big dreams for a franchise hit an unexpected roadblock? Case in point: Isiah Thomas‘ resignation from the Toronto Raptors in 1997. When Thomas joined the Raptors, he wasn’t just another name associated with the organization’s roster—he was ‘THE’ name.

A 12-time All-Star and two-time NBA champion with the Detroit Pistons, Thomas brought instant credibility to a fledgling franchise. As both an executive and part-owner, he had big plans for Toronto, with the ultimate dream of delivering an NBA championship to the city. But that dream came to an abrupt halt.

A closer look at Isiah Thomas’ departure from the Raptors

In November 1997, Zeke shocked the basketball world by resigning as the Raptors’ General Manager. His departure came after a failed attempt to buy out majority owner Allan Slaight. A setback that forever changed his relationship with the team. According to an LA Times report from that year, Thomas decided to sell his 9 percent ownership stake shortly after resigning, cutting ties with the franchise he had hoped to build into something special.

“When I got here, I came here to do a job,” Thomas told reporters on November 21, 1997, just one day after sending in his resignation—via fax, no less, according to the Toronto Star. “I was excited about being a partner … I was excited about building a franchise.” 

If you’re sensing a hint of heartbreak in his words, you’re not alone. Isiah Thomas had poured everything into this organization. “I’ve given you my heart and soul,” he said at the time of his resignation. Thus leaving no doubt about how much the failed buyout and fractured relationship with Slaight stung.

So, what went wrong? Reports from that time suggest the fallout from Thomas’ failed buyout bid was the tipping point. His partnership with Slaight became strained, making it difficult for the two to coexist. An ending that hardly anyone had envisioned.

Slaight acknowledged the legacy Thomas left behind. “The city will miss him,” Slaight said back then. “He [Zeke] does leave behind, on and off the court, a group of bright, talented, committed people.” And without a doubt, the impact of Isiah Thomas leaving the Raptors was huge. So much so that it cost the team their 1996 Rookie of the Year.

Yep, shortly after Zeke’s resignation, Damon Stoudamire also demanded a mid-season trade to the Portland Trail Blazers.

“To see someone every day, to have a dialogue with them, and then boom all of a sudden they’re not there anymore,” Damon said of Zeke’s departure in a Sportsnet documentary. “That messed me up, not gonna lie. I didn’t really know where I stood even though I knew where I stood. I just wanted my way. It was immaturity as well.”

Isiah Thomas’ last piece of advice for the Raptors

When Zeke walked away from the Toronto Raptors, he left the organization with a sharp piece of advice: fix your relationship with the Maple Leafs or face the risk of long-term struggles. Thomas, the Hall of Fame player turned executive, didn’t mince words when he criticized the decision to build the Air Canada Centre without the Leafs as partners.

The 2x NBA champ called it a mistake that hampered the team’s financial footing and would inevitably affect its future. “We should have paid the $20 million or $25 million to the NBA (for delaying the building), played in the SkyDome, and put the money (saved by building a joint arena) into players,” he said, as per Toronto Star.

According to him, the independent arena project drained resources that could have bolstered the roster, making it harder for the Raptors to compete. However, not everyone agreed with Isiah Thomas’ perspective.

Raptors Majority Owner Allan Slaight dismissed his concerns, assuring fans that the Air Canada Centre was on solid financial ground. “There will certainly be money available to go out and get players,” Slaight said confidently. He, however, could not resist taking a jab at Thomas, calling him “an interesting piece of work.”

Zeke too did not shy away from reflecting on his own missteps, admitting he should have done more homework before teaming up with the Raptors. “The picture that was painted to me was very rosy… But I didn’t do the proper due diligence,” he admitted.

All in all, Isiah Thomas’ departure from the Raptors was more than just a farewell. It was a cautionary tale. His insights into the business side of basketball serve as a reminder of how critical sound partnerships and financial planning are in building a lasting franchise.