Senators Prospect Kaden Rolling Now Faces A Different Development Path

As the Windsor Spitfires strategize for future gains with a key trade, players Yakushevsky and Walton shine with notable achievements.

The Windsor Spitfires added another pair of future assets to their draft stash on Monday, sending prospect defenceman Kaden Rolling to the Brantford Bulldogs in exchange for two picks in the 2028 OHL Draft.

For general manager Bill Bowler, the move came down to opportunity on both sides.

"It just made sense for us," Spitfires' general manager Bill Bowler said. "You get two picks and a couple more chances to find players and this is an opportunity for Kaden to play in the league now."

Rolling, 17, was a sixth-round selection by Windsor in the 2025 OHL Draft, but the path to ice time with the Spitfires was blocked. Windsor is carrying nine defenceman on the roster, and Anthony Cristoforo and Thanasi Marentette are playing up front, leaving no opening for the six-foot, 198-pound Rolling this season.

"This year, he couldn't get an opportunity," Bowler said. "The plan was for him to maybe play next year, but this gives him an opportunity to play with Brantford this year."

Rolling has been with the Collingwood Blues in junior A, where he has a goal and five points in 11 games. The Bulldogs have indicated he will likely stay in junior A for the rest of this season before moving into their lineup on a full-time basis next season.

The transaction was one piece of a busy stretch of news around the organization. Last week, NHL Central Scouting Bureau tagged Yakushevsky as an A prospect, putting him in position to be a first-round pick in the 2027 NHL Draft.

"I love this hockey organization, it's very good," said Yakushevsky, who had two assists in his first game in November to give him 21 points in 16 games this season with eight multi-point games for the Spitfires.

And there was more recognition for Windsor on the team side as well. Overage defenceman Conor Walton was named the OHL's West Division academic player of the month for October.

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