Tyler Toffoli has been on a long road leading up to his return to California to play with the San Jose Sharks. It's a bold move for a player who has only been on contending teams in his career, but we have some predictions about Toffoli's Sharks tenure. Toffoli began his career with the Los Angeles Kings, winning a Stanley Cup in his rookie season in 2013-14. He had just 12 goals and 17 assists in 62 regular season games, but stepped up in the postseason with seven goals and seven assists. Toffoli stayed with the team until 2020 when the Kings traded him to the Vancouver Canucks at the trade deadline.

The trade to Vancouver started a journey across Canada for Toffoli, who signed a four-year contract with the Montreal Canadiens after the season ended. Toffoli's first season with the Canadiens ended in an improbable run to the Stanley Cup Finals, where they upset the Toronto Maple Leafs, Winnipeg Jets, and Vegas Golden Knights before falling to the Tampa Bay Lightning. The Canadiens regressed the following year, so they sent Toffoli to the Calgary Flames at the trade deadline. Toffoli's career-best season came in 2022-23 when he had 73 points in 82 games.

The Flames traded Toffoli to the New Jersey Devils to start the 2023-24 season, but they had a poor season and began selling players at the deadline. It led him to play with his fourth Canadian team in five seasons when they traded him to the Winnipeg Jets. Toffoli had a good run with the Jets but needed some security in his career. The rebuilding San Jose Sharks offered him a four-year, $24 million contract, which he signed to join young stars Macklin Celebrini and Will Smith.

Tyler Toffoli gets traded before contract ends

New Jersey Devils right wing Tyler Toffoli (73) looks up as the puck deflects off the crossbar behind San Jose Sharks goaltender Kaapo Kahkonen (36) during the second period at Prudential Center.
© Vincent Carchietta-USA TODAY Sports

Toffoli is no stranger to getting traded at the deadline. He has been part of these trades three times in his career, and it feels like a fourth coming in this contract. Toffoli's contract has a no-move clause, so it's in his hands whether he moves. Toffoli will be 36 when his contract ends, and it seems like he's content with finishing his career in California. He married Cat Belanger, a California native, so he and his family want to live at home.

The thing is that Toffoli is a competitor first and foremost. He may think that the Sharks are a good fit for him right now, but if they still aren't contenders in four seasons, Toffoli may want to make one more run at a Stanley Cup. It feels like Toffoli could waive his clause at the trade deadline of his fourth year if the Sharks aren't a playoff team.

Will the Sharks be a contender in 2027-28? They have the young pieces to contend, but Celebrini and Smith may not be able to do it alone. The Sharks have some holes in their lineup on defense and in net, but the drafting of Sam Dickinson in the first round of the 2024 NHL Draft could help solve that problem. They prioritized defense this offseason by drafting Leo Sahlin Wallenius in the second round and trading for Jake Walman. The one thing standing in the Sharks' way of being a contender is goaltending, as Magnus Chrona looks like the best choice.

Sharks don't make playoffs during tenure

Chrona being the Sharks starting goaltender of the future doesn't look like the best choice for their playoff chances. Chrona had a .859 save percentage and a 4.71 goals-against average in nine games this past season. It was only his first professional season, but he will need a lot of improvement to be a starting goalie on a contender in four seasons. Banking on Chrona as the reason the Sharks won't make the playoffs isn't the most reliable opinion since they could easily acquire a goaltender.

The Sharks could acquire a serviceable goaltender for not many assets. The 2023 Vezina Trophy winner Linus Ullmark went to the Ottawa Senators for a 25th overall pick and a couple of depth pieces. Jacob Markstom went to the New Jersey Devils for a first-round pick and Kevin Bahl. If Celebrini and Smith are stars, and Dickinson soon debuts and looks like a franchise defenseman, the Sharks will move to acquire a starting goaltender.

It'll be hard for the Sharks to dig themselves out of their hole before Toffoli's contract ends. They will likely draft in the top half of a good class in 2025, but they'd need that selection to contribute within three years. These two bold predictions go hand in hand, as they could both be wrong if Tyler Toffoli sticks with the Sharks and re-signs, as they should be playoff contenders in a hypothetical second contract.