After a trade with the Flyers earlier in the week, new Toronto Maple Leafs general manager John Chayka was busy again on Friday, acquiring Darren Raddysh from the Tampa Bay Lightning for a 2026 fifth-round pick. Raddysh also agreed to terms on an eight-year contract with an $8.5 million AAV with the Leafs. Mike Clifford wrote more about the trade in the Fantasy Take.

The emergence of Raddysh was a complete surprise in 2025-26. So much so to me that I identified him as one of two players that completely caught me off guard (Matthew Schaefer was the other). Make no mistake: Raddysh is a sizeable gamble for the Leafs. He is 30 years old and has only one standout season in which he jumped from six goals and 37 points to 22 goals and 70 points. Raddysh shot at a 10.4% rate in 2025-26, which was below the 4-6% that he averaged in previous seasons. For the term and cap hit being invested in him, Raddysh doesn't exactly have a proven track record of success.

However, this signing has the potential to pay off in a big way for the Leafs. Raddysh and his booming right shot from the point could pay dividends on a power play that also includes Auston Matthews, William Nylander, and perhaps even Gavin McKenna. To compare, Morgan Rielly has seven power-play goals over the last six seasons. Raddysh had 10 power-play goals last season alone. If Raddysh was no fluke last season, then that's an upgrade for everyone on the Leafs' top power play.

With a bit of luck (the draft lottery) and some quick changes, the Leafs are pushing for a minor retool to win now instead of a total rebuild. They're probably not done either. The trades this week signal that Morgan Rielly is even more likely to be on his way out of town. At age 32 and averaging just under 40 points for the past two seasons, Rielly might be better suited to be a supporting power-play piece as opposed to a PP1 quarterback. Rielly was held to just 6 power-play points last season while shifting on and off the top power play (leaning toward off later in the season). Rielly had the same number of power-play points as rookie Easton Cowan and fewer power-play points than Matias Maccelli or Max Domi.

As for Tampa Bay, I doubt they're done either. Charle-Edouard D'Astous could be a name to watch, as Cliffy mentioned in the Fantasy Take. John Carlson should pop up on their radar, as he is not expected to re-sign with the Ducks. Alex MacLean expects Carlson to command nearly $8 million per season in his salary projections, and that number could go even higher with Raddysh now off the market. However, Carlson is coming off a 60-point season, is a right shot like Raddysh, and was an active contributor on Anaheim's power play. The fact that he is 36 might be viewed as a problem, but Tampa is trying to keep its window open, so Carlson could make sense on a short-term deal. Carlson should have plenty of interest in the free agent market.

–

Jonathan Toews officially announced his retirement from the NHL on Friday. Toews returned for the 2025-26 season with his hometown Winnipeg Jets after his career was paused for two seasons. Prior to that, Toews spent 15 seasons with the Chicago Blackhawks, where he won three Stanley Cups, a Conn Smythe Trophy, a Selke Trophy, and numerous All-Star Game appearances. Toews was also named one of the 100 Greatest NHL Players in 2017 as an active player. Adding in his contributions to Canada in the World Juniors and the Olympics, Toews will likely be nominated to the Hockey Hall of Fame once he becomes eligible.

With such a storied career, Toews often seemed like a better real-life player than fantasy league option. His career highs of 35 goals and 81 points were set in 2018-19, after he won his three Stanley Cups. Toews only exceeded 70 points twice in his career, which never made him an elite option at the deep center position. In his prime, Toews would have been universally rostered. Any fantasy league discussion should not take away from his accomplishments captaining a Chicago team that won three cups in the span of six seasons. However, the distinction between "real life" and "fantasy" is important for fantasy leaguers, especially for beginners. Understanding a league's scoring system is key.

How quickly time passes. I was in attendance for the 2006 NHL draft when Toews was drafted third overall by the Blackhawks (the only NHL draft that I have ever attended in person.) The player that was picked second overall in that draft has also been in the news recently: Jordan Staal. That draft was a memorable one for me because it featured a very solid top 5: Erik Johnson, Staal, Toews, Nicklas Backstrom, and Phil Kessel. That draft happened 20 years ago, when the Stanley Cup champion was… the Carolina Hurricanes.

–

In case you missed it, Troy Terry is expected to miss the start of the 2026-27 season, as he underwent hip surgery to address an impingement and labral tear. With a recovery time of 5-6 months, Terry would likely return sometime in November or early December. Terry managed to gut it out during the playoffs with 11 points in 12 games and even five hits – three more than he had during the entire regular season!

In terms of players who could see an increase in icetime, fellow right winger Beckett Sennecke could be one player to target in drafts. Sennecke will have an early opportunity to build on his 60-point rookie season. Icetime and power-play time are divided up fairly evenly in Anaheim, but the Terry injury should at least prevent Sennecke from falling down what is becoming a deep Ducks lineup.

–

Congratulations to the Toronto Marlies, the winner of this year's Calder Cup! The Marlies downed the Chicago Wolves 4-3 and win the final 4 games to 1. The Stanley Cup hasn't been won by a Canadian-based team in over 30 years, but the Calder Cup will remain in Canada for the second year in a row (the Abbotsford Canucks won last season). Between the Raddysh acquisition and the Marlies Calder Cup win, Friday was a nice day to be a Leafs fan.

Goalie Artur Akhtyamov has been named the Calder Cup playoff MVP. Akhtyamov has a 2.22 GAA and .923 SV% during the playoffs (I don't think that includes Friday's game). Akhtyamov has an outside chance to be the Leafs' backup goalie next season, but he'll need to compete with Samuel Ersson and Dennis Hildeby for that spot. For more on Akhtyamov, see his Dobber Prospects profile. You can also purchase the Prospects Guide at the Dobber Sports store to view information such as his upside, 3-year probable, expected NHL arrival, draft advice, and more.

📢 advertisement: