Kawhi Leonard gave the Toronto Raptors some financial breathing room, settling for $11 million less than the maximum he could have received. However, that does not necessarily mean Toronto got a bargain. His two-year, $115 million extension gets Toronto its proven championship winner back, but it carries a financial commitment that leaves little room for error. 

And despite Leonard waiving his 7.45 million trade kicker, ESPN insider Tim MacMahon sees a much bigger concern hiding behind the apparent savings.

“I get it. Getting Kawhi Leonard raises the ceiling to championship possibilities for Toronto,” MacMahon said, appearing on ESPN’s NBA Today. “I get it. Let’s not act like this is not a massive risk, okay?”

While MacMahon acknowledged Leonard’s championship-winning CV, the former Clippers star’s durability issues, including the persistent knee and ankle trouble over the last few seasons, didn’t make this $115 million deal justified in his eyes.

“This is a guy who’s played 60-plus games three times. Three times in the last nine years. Now one of those, 60 on the nose, was in Toronto, and he led them to a title. But $115 million for a player with those durability issues, right? In his mid-30s. That is a massive contract. That’s not a discount deal. A discount deal is Kevin Durant: a two-year, $90 million extension. This is $25 million more than that,” added MacMahon.

Leonard was in the last year of a three-year, $149.5 million deal he signed with the Clippers in January 2024. On his new deal, Leonard will get an average of $57.5 million annually compared to Durant’s $45 million.

That distinction matters because Toronto committed an enormous amount of money to a player entering his mid-30s, while knowing that his recent career has been defined as much by managing his body as by his production.

The championship history is also why this gamble is difficult to dismiss.

Kawhi Leonard has already shown Toronto what can happen when its medical staff successfully manages his workload and has him ready for the postseason. Seven years later, the Raptors are essentially betting on another version of that formula.

There are still compelling reasons to make that bet. 

Last season, Leonard averaged a career-high 27.9 ppg and scored a personal-best 55 points in one game. It showed that his offensive ability remains elite. His mid-range scoring, decision-making, and experience can still change the equation for a team with championship ambitions.

The problem is keeping that version of Kawhi Leonard on the floor. 

He operated under strict load management last season, including limitations on playing back-to-backs. Even with that careful approach, his knee issues resurfaced late in the season, adding another layer to Toronto’s calculations.

Kawhi Leonard waiving his trade kicker helped the Raptors navigate their immediate cap situation. But those savings don’t eliminate the consequences if injuries prevent him from consistently taking the floor. 

For the Raptors, that is the trade-off.

The team gave up Brandon Ingram, Gradey Dick, two first-round picks, a first-round pick swap, and two second-round picks to the Clippers to acquire Leonard this summer. The trade was reportedly agreed to on June 30, but put on hold while the NBA investigated the Clippers for salary cap circumvention involving under-the-table deals for Leonard.

That saga ended with Clippers owner Steve Ballmer getting suspended without pay for a year, the organization being fined $30 million, and Leonard being fined $700,000. The 2019 NBA champion’s contract, however, was not voided.

The next two seasons will determine whether the apparent savings around Leonard’s extension actually matter. If Toronto can keep him healthy enough to make another postseason run, $115 million becomes the cost of chasing another ring. If availability again becomes the defining issue, MacMahon’s distinction between a discount and a massive financial gamble will become increasingly difficult to dismiss.