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Why the Maple Leafs may not have overpaid for Darren Raddysh

Darren Raddysh's eight-year deal looks like an overpay for the Toronto Maple Leafs now, but that could change down the line.
Apr 7, 2026; Ottawa, Ontario, CAN;  Tampa Bay Lightning defenseman Darren Raddysh (43) is seen in a game agains the Ottawa Senators during the first period at Canadian Tire Centre. Mandatory Credit: Keito Newman-Imagn Images
Apr 7, 2026; Ottawa, Ontario, CAN; Tampa Bay Lightning defenseman Darren Raddysh (43) is seen in a game agains the Ottawa Senators during the first period at Canadian Tire Centre. Mandatory Credit: Keito Newman-Imagn Images | Keito Newman-Imagn Images

The idea of the Toronto Maple Leafs paying $8.5 million for Darren Raddysh over the next eight seasons is something that screams of an overpay. Toronto is banking that Raddysh’s career year this past season is not an outlier, while also hoping that he can replicate his production, at least for the next few seasons.

Likely, the organization agreed to go the full eight years to keep his AAV down. Had the Maple Leafs, or any other team, wanted to sign him to a shorter-term deal, the AAV would have been much higher. That’s why this deal resembles Chris Tanev’s contract significantly.

But that’s not the reason why Raddysh’s contract might not look like an overpay down the line. In particular, it’s the rising salary cap that could make the deal look better.

No, the dollars won’t magically decrease over the years. What will decrease, however, is the proportion of cap allocation that the cap hit will consume.

As it stands, the 30-year-old’s $8.5 million cap hit will account for 8.2% of the Maple Leafs’ cap allocation this upcoming season. That’s working off the $104 million cap ceiling. In 2027-28, the ceiling will jump to $113.5 million. With Raddysh’s cap hit remaining the same, the cap allocation will drop to 7.5%.

Suddenly, the deal doesn’t look all that bad.

By 2028-29, the cap ceiling will spike to $123 million. That should water Raddysh’s cap hit further, down to 6.9%. The overall proportion of cap allocation should make the deal look better as the cap increases.

But there’s another reason why Raddysh’s contract might not be as bloated today as it could be down the line.

Cale Makar and Quinn Hughes’ contracts should become nuclear blasts

Darren Raddysh was the best defenseman available on the market. Unfortunately, that’s the sad state of this year’s free-agent market.

But there are two other defensemen in line for new contracts. Those would be Cale Makar and Quinn Hughes. Now, I’m not comparing Raddysh to Makar and Hughes. But when the former Norris Trophy winners get paid, they’ll make Raddysh’s cap hit look like chump change.

Both Makar and Hughes could fetch well over $16 million per season. That’s roughly double Raddysh’s AAV. And it would make his contract look like a deal.

And it would also make sense. If an elite, Norris Trophy-winner like Makar gets, say, $15 million, it would seem commensurate that Raddysh, not quite an elite blueliner, gets $8.5 million.

Other elite defensemen should get paid well in the coming years. For instance, if Matthew Schaefer continues the path he’s on, how much could he get when his entry-level deal is up?

In the end, time is on the Maple Leafs’ side. If Raddysh can live up to his deal, at least during the first half of it, John Chayka could look like a genius.

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