SIMMONS: Bobrovsky, Kawhi are gambles worth taking for Leafs, Raptors

What a mind-boggling, hugely optimistic two sporting days this has been in Toronto

Published Jul 01, 2026  •  Last updated 16 minutes ago  •  5 minute read

Keith Pelley, President and CEO of Maple Leaf Sports and Entertainment, addresses media at Scotiabank Arena in Toronto on March 31, 2026, following the firing of Toronto Maple Leafs GM Brad Treliving. Photo by Ernest Doroszuk /Toronto Sun

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Kawhi Leonard holds the NBA Finals MVP trophy during the Toronto Raptors victory parade in 2019. Getty Images

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But on Tuesday, after a few days of rumours, the fairytale of Kawhi and the Raptors began all over again. The master stroke in all of this was that Webster could bring in the 35-year-old Kawhi and at the same time rid himself of the $40-million per season contract given to Brandon Ingram.

Pat Gillick, the best general manager Toronto has ever known, used to say that the best GMs in the business were the ones who fix their mistakes quickly after making them. Webster signed Ingram for $120 million over three seasons and then watched him disappear at playoff time.

Now he’s gone and there is Raptor hope, perhaps even greater than there was when Kawhi joined the team against his best wishes back in the summer of 2018.

Sergei Bobrovsky of the Florida Panthers looks back into the net following a by Matthew Schaefer of the New York Islanders. Getty Images

Bobrovsky, the goaltending wizard, is three years older than Kawhi, and unlike the power forward, he is not coming off an excellent season. Bobrovsky was all but terrible in goal for a rather helpless Florida Panthers team this past season.

If there’s a reason to doubt him, other than the obvious statistical drubbing of this past season, it’s that Bill Zito, the master decision-maker in the NHL, didn’t want to commit to him in Florida anymore. Zito was willing to go long-term with Brad Marchand last season, who is one year older than Bobrovsky.

Zito chose to not sign Bobrovsky, who had been central to the two straight Stanley Cup wins by the Panthers. Zito went to Jacob Markstrom instead. For a savings of about $1 million a year. If Zito is giving up on Bob knowing that he thinks Florida can take another run at the Stanley Cup, then there is reason to wonder about this signing.

But if you know Bobrovsky at all, doubt him at your peril. He is unlike so many who have played goal in the NHL. He is a workaholic. He is a conditioning freak. He is steadfast about how he does his job and how he expects others around him to perform.

Were his numbers last season the result of bad play or being on an incomplete team after three straight years playing for the Stanley Cup? Years ago, the Leafs signed Ed Belfour after his worst season in Dallas. The move was highly criticized. Belfour was brought in to replace Curtis Joseph.

All he did at the ages of 38 and 39, was play goal better than any Leaf had played since Bernie Parent and Jacques Plante shared the duties in 1974.

This is a gamble for Chayka, who was told to compete immediately with the Leafs and is proceeding as well as could be expected with those directions. The top three free agents available a month ago were Bobrovsky, defencemen Darren Raddysh, and winger Alex Tuch.

Chayka got two of them.

He traded Joseph Woll to Philadelphia and Brandon Carlo to St. Louis and the $7 million saved on the deals was the same amount he used to sign Bobrovsky. That’s sound asset management.

The other signings that followed on Canada Day were not really gambles. Just more old bodies making too much money.

The Leafs paid $4 million to Colton Sissons, who had 11 points for Vegas last season. They paid $4 million for Auston Matthews’ old friend, Jack Roslovic, who seems to be a quintessential Leaf. He has one playoff goal in his last 15 Stanley Cup games. The bottom of the roster is older and thicker and experienced — the pickup of Nick Paul for the Leafs’ third goalie, Dennis Hildeby, might have been the most impactful roster move after adding Raddysh last month and then signing Bobrovsky on Wednesday.

The Leafs are now three deep in goal, better on defence with Raddysh in and Carlo out, still in need of more help in the back end, and deep up front with too many third-liners and fourth-liners making what used to be second-line money.

Will the Leafs be Stanley Cup contenders if Bobrovsky returns to form? It’s impossible to know right now. Because we don’t know enough about Jim Hiller as a head coach. Because we don’t know which Auston Matthews will be at training camp in September. Because we don’t know if Chris Tanev can play 65 games, which is about the number the Raptors will expect from Kawhi.

Keith Pelley is smiling somewhere right now because everything is going his way. His teams are rolling the dice, playing backgammon and hoping for double sixes at the end. The Raptors are betting on the 35-year-old Leonard. The Leafs are betting on a 38-year-old goalie coming off his worst season.

These are gambles no doubt, gambles worth taking a shot at it for franchises who have been too conservative and proper for far too long.

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