Maple Leafs' Darren Raddysh deal will soon become impossible under the NHL's new CBA

During the offseason, the Toronto Maple Leafs completed a sign-and-trade with the Tampa Bay Lightning, which brought defenseman Darren Raddysh to the franchise.

Raddysh signed an eight-year deal worth $68 million, which means he will get paid an AAV of $8.5 million. In many ways, it was a similar sign-and-trade to the one the Leafs completed in 2025 with Mitch Marner going to the Las Vegas Golden Knights. In order to get that eighth year, the sign-and-trade was necessary.

Under the current CBA rules, you can only sign an eight-year deal with your current team. However, Raddysh's contract is one of the last of its kind. The CBA is about to change, and Raddysh has the potential to serve as a test case for the NHL's new direction.

Toronto used the outgoing CBA to give Raddysh an eighth year it could not offer next month

As of September 16, the new NHL CBA comes into effect. Under the new CBA rules, players can no longer sign eight-year deals. The max term you can sign with your current team is seven years. Outside free agents are being capped at six years.

Moving forward, contracts like Raddysh's can no longer be signed. This makes him a fascinating player going forward. The Leafs did a sign-and-trade because they wanted that eighth year. It's an interesting move, especially when you consider that Raddysh will be 38 at the end of the contract.

General Manager John Chayka made this decision intentionally. By making this move, he has an extra year of control with Raddysh's contract. It also gives the Maple Leafs a larger window to make things happen. Toronto is betting that Raddysh's 70-point breakout was sustainable enough to justify committing through his age-38 season. The timing was perfect, as this would be the last time Chayka could acquire a 70-point right-handed defenseman for eight years.

Raddysh may become the final test of whether an eighth contract year was actually worth the risk

According to NHL.com, the Toronto Maple Leafs sign-and-trade for Raddysh was described as “aggressive.” In the eyes of some analysts, there is a lot of risk with the move due to the fact that Raddysh will be 38 when the deal is over. Furthermore, the contract was awarded after just one big season.

However, with the new CBA, Chayka seemingly saw a risk-vs.-reward ratio that he could get behind. With this contract, Raddysh stands to make a total of $68 million. That is a hefty total of $8.5 million per season. The eighth year gave Toronto more term certainty, but it also added another season of age-related risk. Under the new CBA, future teams making a similar bet on an outside free agent will have fewer years available to spread that commitment across.

In the past, teams loved giving players eight-year deals. It brought lower AAVs, more guaranteed money for players, and stronger recruiting leverage. On the other hand, the league opted to get rid of it because they felt like teams were exploiting the system by frontloading deals.

Raddysh therefore becomes one of the clearest final examples of the outgoing system. If he remains a top-pair, power-play defenceman deep into the contract, Toronto will have extracted value from an eighth year that future teams can no longer offer. If his decline arrives early, the deal will show exactly why that extra season carried so much risk.

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