Wanderers sign midfielder Caden Trestrail to Exceptional Young Talent contract

The Halifax Wanderers made their second addition this transfer window, inking teenage midfielder Caden Trestrail to an Exceptional Young Talent through the 2028 CPL season. The club also has an option for 2029.

Trestrail, 18, hails from Diego Martin, Trinidad and Tobago. He represented Trinidad and Tobago at the U-17 and U-20 levels but has Canadian citizenship through his grandparents.

He recently made several first-team appearances for Defence Force in the Trinidad and Tobago Premier Football League before a mid-season move to San Juan Jabloteh, where he collected two goals and three assists in eight matches.

“There are two things that really impressed me with Caden: his technical proficiency and his understanding of the game at a level above most players his age,” Wanderers head coach and general manager Vanni Sartini said in a press release.

“He is a very young player but someone we’re really excited about as we work to develop him at the CPL level.”

Previously, Trestrail played in the 2025 Concacaf U-17 Championship, scoring once while adding two assists in four matches. He recently made four appearances for the U-20 national team.

“I’m beyond excited to be a part of this group full of quality players and to play in the CPL because it’s a very competitive league with high levels of opposition that I’m excited to compete against,” Trestrail said.

“I think Halifax is a great place for me to take the next step up because of the players and coaches that can help me develop along with the amazing connection between the fans and the team.”

Current Wanderers Andre Rampersad and Ryan Telfer are regular call-ups for the Trinidad and Tobago national team.

Editor's Note: This article is part of our free coverage.

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Cover Photo Credit: Halifax Wanderers FC