Maple Leafs Could Complete Family Reunion This Summer
Toronto acquired defenseman Darren Raddysh from the Tampa Bay Lightning in a sign-and-trade back in June, signing him to an eight-year, $68 million contract as part of the deal. Now the Maple Leafs are being connected to his younger brother, Taylor, a winger currently on the New York Rangers.
A Wish Their Father Never Got To See
Darren and Taylor grew up in Caledon, Ontario, roughly 40 miles from Scotiabank Arena, playing mini-sticks in the family basement while wearing Maple Leafs jerseys as kids.
Their father, Dwayne, always hoped to see at least one of his sons play for the team he raised them to love, but he died on March 3 following a battle with pancreatic cancer, just months before Darren's trade to Toronto.
"It means the world," Darren told NHL.com after the deal. "My brother and I grew up being Leafs fans. We go with our dad to watch the games."
Toronto Sun columnist Steve Simmons first floated the idea the same day Darren's trade was announced. Taylor is entering the final year of his contract at a modest $1.5 million cap hit, and with the Rangers in the middle of a retool, moving a pending free agent for a return makes sense for New York.
Toronto still lacks a cheap bottom-six winger with a real scoring touch, something Taylor could provide after posting a career-high 20 goals and 37 points with Chicago back in 2022-23.
He added a 20-assist season with Washington in 2024-25. Recent additions like Nick Paul, Brandon Duhaime, Teddy Blueger, and Colton Sissons have mostly been brought in to fortify Toronto's defensive depth, not add offense, leaving a gap Taylor could fill.
What It Would Cost
NHLTradeRumor.com's Rob Ellis published a proprietary trade-value model this week estimating a fair starting offer at a 2027 fifth-round pick, or a sixth-round pick paired with a secondary prospect.
Given the low term and modest cap hit, it's a low-risk swing Toronto could make without disrupting its other offseason plans.
To be clear, nothing suggests Taylor has requested a trade or that Toronto has made a formal offer.
But with the family connection already in place, a pretty logical roster need on Toronto's side, an expiring, affordable contract on New York's side, and some big names out there independently floating the idea from multiple angles, the pieces are there for John Chayka to make it happen if he wants to.
