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The Kiefer Sherwood extension is the reason Bobby McMann is no longer a Maple Leaf


PUBLICATION
Charlie McAfee
March 12, 2026  (7:27)
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Toronto Maple Leafs forward Bobby McMann (74) reacts to a goal by forward John Tavares (91) against the Carolina Hurricanes during the first period at Scotiabank Arena.
Photo credit: John E. Sokolowski-Imagn Images

While Maple Leafs fans should rightly be upset at management for losing Bobby McMann, some blame needs to be placed on Kiefer Sherwood thanks to his massive pay raise that shut Toronto out of a reasonable extension.

Sherwood signed a five-year, $5.75-million extension with the San Jose Sharks, and while he has certainly earned the pay raise, it also set a huge precedent.
Until the last couple of seasons, Sherwood wasn't seen as much from an offensive standpoint, but broke out over the past two seasons which added a whole new dimension to his game - so his price shot up.

What Kiefer Sherwood's extension meant for Bobby McMann's asking price

That means late-bloomers or players who added another facet to their game late in their careers are going to become expensive with less of a guarantee they'll keep up consistently.
McMann is nearly 30, and he's looking to cash in on the last two years of play before he potentially phases out of the league as he gets older. You also can't blame him for looking at Sherwood; a near-identical player, and not think you're worth that much at least.
The asking price for McMann at even $4-million is a bit high, but still a lot more reasonable than nearly $6-million. If Toronto approached him earlier in the season with an offer like that, he may have taken it.
Instead, the team waited to see if they were playoff contenders and built up McMann's price even more considering he was a bright spot in a dark stretch.

The Maple Leafs were never going to pay $5-million for a 29-year old support piece

But from a business standpoint, you can certainly see why investing in a near 30-year old for long-term could backfire.
McMann's best asset as a player is his speed, he's one of the fastest in the entire league. What's the first thing to go as you get older? Quickness.
Ask John Tavares, Chris Tanev, Morgan Rielly and even former players like Max Pacioretty about how age slows you down and you quickly see why Toronto might be hesitant.
Say McMann plays another two seasons with top-tier play, but struggles to stay consistent into his mid-30s. Will Toronto be able to afford that decline, while also paying him quite a considerable amount for a middle-six forward? Unlikely.

McMann joins a growing list of Maple Leafs priced out by their own cap decisions

That question though isn't new. Toronto historically has lacked a killer instinct in paying their players. We saw Zach Hyman leave town because the Maple Leafs were a little hesitant to invest long-term.
117 goals in his first three seasons with the Oilers was the end result, and Toronto could have reaped those benefits had they not been so reckless elsewhere.
They had 50% of their cap dedicated to four forwards, with a need to improve in other area. Hyman was a perfect complement to Auston Matthews, and right now Matthews is missing that x-factor to help elevate him again.
Even before then, Toronto decided to let James van Riemsdyk go after a 36-goal, 54-point season when he was only 29. He's still playing currently at 36 and is putting up solid numbers (27 points in 56 games).
Sound familiar?
Those aren't the only names, as you can include Connor Brown and Tyler Bertuzzi in there as well. You start to see a pattern where Toronto is happy to develop players but never reward them - and who wants that?
Bobby McMann was priced out from the start thanks to the Sherwood deal, but it's not as if this is a one-time mistake for the Maple Leafs, but another misfire from management.
POLL
MARS 12|849 ANSWERS
The Kiefer Sherwood extension is the reason Bobby McMann is no longer a Maple Leaf

Who is most to blame for the Maple Leafs losing Bobby McMann?

Sherwood's extension475.5 %
Management51460.5 %
McMann for his asking price16119 %
Core Four contracts12715 %
List of polls

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