
Jay Rosehill spoke highly about his time playing with Phil Kessel on the Toronto Maple Leafs. Rosehill praised Kessel’s talent and personality for being a bright spot when the team struggled.
Kessel dealt with high expectations during his time with the Maple Leafs. He was acquired in a blockbuster trade with the Boston Bruins and was relied upon to help get Toronto into the playoffs. While Toronto experienced their fair share of ups and downs, Kessel consistently led the Leafs in goals and points.
In recent years, many of Kessel’s former teammates have shared their fond memories of playing with him. The majority of stories involve imitations of the American winger’s voice, highlighting his sense of humor.
Kessel was not known for being an active presence in the media and rarely gave interviews. However, in the Leafs dressing room, the American was well-liked and respected by his teammates.
Jay Rosehill Opens Up on Playing with Phil Kessel

GettyTORONTO – DECEMBER 14: Phil Kessel #81 of the Toronto Maple Leafs celebrates goal against the Ottawa Senators during action December 14, 2009 at the Air Canada Centre in Toronto, Ontario, Canada. (Photo by Abelimages/Getty Images)
Jay Rosehill opened up about playing with Phil Kessel and what he was like as a teammate.
Rosehill was a member of the organization from 2008 to 2012, splitting time between the Leafs and Marlies. He echoed many of his former teammates’ sentiments about playing with Kessel.
The Leafs Morning Take co-host described Kessel as a unique individual and proof that people should not judge a book by its cover. Rosehill noted that while he did not look like a physically fit professional athlete, the American was incredibly talented.
Rosehill said Kessel knew what he was capable of, which often surprised his teammates.
“[Kessel is] such a funny, unique individual, man. I just don’t know how the speed and the talent comes out of his body. He kind of doesn’t look like an athlete. His voice, he likes to whine and drag his feet and he’s always in sweatpants and flip flops,” Rosehill told The Game Plan. “He’s not what you think of when you think of a premier athlete. But for whatever reason, he knew how to get it down and had tons of success.”
Rosehill Enjoyed Being Kessel’s Teammate
Rosehill also revealed that he enjoyed being Kessel’s teammate. He noted that the American winger was a joy to be around and created several memorable moments.
“It was fun playing on his team,” Rosehill told The Game Plan. “[He was] super talented. But there’s no shortage of stories out there for Phill ‘The Thrill.’ He’s quite the character, no doubt about it.”
Fans did not see that side of Kessel until the HBO 24/7 series documented the team ahead of the 2014 Winter Classic. His interaction with then-head coach Randy Carlye went viral due to his ‘Good one, Randy’ line.
It was clear that the three-time Stanley Cup winner was quite the character in the locker room. After his exit from the Leafs, Kessel remained a beloved teammate. His teammates from the Pittsburgh Penguins and Vegas Golden Knights‘ Stanley Cup-winning teams have also shared fond memories of him.
Jay Rosehill Opens Up About What It Was Really Like Playing With Phil Kessel