It wasn't that long ago that the winger was putting up decent offensive numbers in a shutdown role for the Pittsburgh Penguins.

Philip Tomasino was nearing the end of a shift midway through the final game of the 2024-25 regular season when his Pittsburgh Penguins teammate Sidney Crosby hopped on the ice.

As his linemates retreated to the bench to change for the Penguins’ top trio, Tomasino battled away, helped force an offensive-zone turnover and was suddenly on a mini 2-on-1 with the Penguins captain.

Tomasino waited for the Washington Capitals defenceman to make the first move and then threaded a cross-slot pass to Crosby for a beautiful one-timer goal.

The winger would add a goal that night, finishing his first season in Pittsburgh with 23 points (11 goals, 12 assists) in 50 games.

Just a year and five months later, he’s now battling for an NHL roster spot with the Ottawa Senators.

“I remember him a little bit as a player,” Ottawa coach Travis Green said after practice Friday. “I thought he was a good, up-and-coming player in the league. You know, it seems like he got derailed a little bit. He’s looking for opportunity and potentially there is one.”

Indeed, Tomasino hit a major roadblock in 2025-26, unable to build off the success of his previous campaign. After recording one assist in his opening nine games, Pittsburgh waived him and he cleared.

A month later, he was traded to the Philadelphia Flyers but spent the rest of the year in the minors.

What had happened to the former first-round pick?

“I mean, honestly, I don’t know,” Tomasino said. “I don’t know if I necessarily have an answer. I mean, I think I try to look at everything one day at a time. I mean, I’m not too worried about what’s happened in the past. And whatever’s happened, happened.”

The Mississauga native regrouped in the summer, accepting the reality that he would have to prove himself all over again on a two-way contract. On July 1, he signed a one-year, $900,000 US deal with the Senators.

Tomasino switched up his off-season program. He began training with renowned strength and conditioning coach Andy O’Brien, Crosby’s personal trainer for over two decades and now the Toronto Maple Leafs’ head of sport performance.

“Just looking at my game, maybe focusing on some areas in the off-season that maybe led to me not being full-time the last year,” Tomasino said. “Just trying to work on stuff like that, getting stronger. I put on some weight from last year just to kind of change some things up.”

Tomasino was selected 24th overall by the Nashville Predators at the 2019 NHL Draft. In his second professional season, he made the jump to the big club, collecting 32 points (11 goals, 21 assists) in 76 games. He has 95 points in 218 career NHL games.

Tomasino skates well, works hard and has a decent wrister. It’s just practice, but he didn’t look out of place on a line with Tim Stützle and William Eklund on Friday.

“I mean, that was pretty cool,” Tomasino admitted. “Obviously, two really high-end guys, really fast. Listen, it was awesome. Hopefully I get another opportunity to skate along with those guys and make the most of it.”

The organization seems to be giving the 25-year-old a solid shot at cracking the opening night lineup. He played on a line with Shane Pinto and Michael Amadio in a 6-1 loss to the Maple Leafs on Wednesday, recording three shots and a minus-1 rating in 18:50 of ice time.

“I’m not going to sit here and say he’s just jumped off the page for us, but he’s a player that intrigues us,” Green said. “He’s played some (NHL) games before, he’s got some big speed in this game. I think it’s important that a player like that is around our team for us to get a look at them.”

The Senators have 13 NHL contracts up front, but that doesn’t mean there aren’t early spots up for grabs. Ridly Greig will miss the first two games of the regular season due to a suspension.

Warren Foegele has only just resumed practising following an undisclosed injury. There also is pressure on 24-year-old centre Stephen Halliday, who is waivers-exempt for the next few months at least.

“I think my game fits into the style they want to play,” Tomasino said of Green’s system. “I mean, they want to play fast; they want to be on the attack. I think I’m at my best when I’m pushing the pace with the puck, taking pucks to the net, being fast.”

Tomasino will get one more opportunity to show his worth before final cuts. The Senators will wrap up the pre-season with split-squad games against the Montreal Canadiens on Saturday night. A week later, the games start for real.

“My goal heading into this year was just to do whatever the coaches kind of need me to do,” Tomasino said, “whether that’s, like you said, a shutdown role, whether it’s fourth line, first line, whatever it is. 

“I think my mentality is just to do whatever I can to be on this team and help this team win.”