Trading Timothy Liljegren is a missed opportunity for him and the Maple Leafs

Timothy Liljegren has packed his bags and will board a flight to Northern California early Thursday morning to leave the only NHL franchise he has known for seven and a half years.

On Saturday night he will make his home debut as a San Jose Shark, perhaps even as a top pairing partner with Mario Ferraro when they take on the Vancouver Canucks.

How Toronto Maple Leafs fans should feel about this really depends on your perspective.

Yes, Liljegren was a first-round pick in 2017 when he went 17th overall after falling to the overjoyed Leafs. They chose him over other potential stars, players like Josh Norris, Robert Thomas, Jake Oettinger and Filip Chytil, who are doing more damage elsewhere in the NHL these days. They didn’t pick up healthy scratches or sit at the end of the bench at crucial moments.

Liljegren fought his way up the organization for years, starting at age 18 with the Marlies. He won an AHL championship there as a kid and then took on an important role with the Leafs starting in 2021-22.

It was never a steady increase. Whenever there seemed to be progress, there was a setback or hurdle.

And now he’s gone in exchange for two mediocre draft picks (a third-rounder and a sixth-rounder) and a strong defenseman (Matt Benning) who may not stay in Toronto much longer.

“He was kind of always on alert; He always had to prove himself (to the Leafs),” said Peter Wallen, Liljegren’s longtime agent, shortly after the deal was announced Wednesday night. “We always had the feeling that they didn’t really like him. They liked him. But they didn’t love him. I don’t know.

“It was hard. But that’s why I don’t understand it, because he really tried hard (tried to get better). I don’t understand why they didn’t want to continue with him.”

Wallen and Leafs general manager Brad Treliving led tough negotiations over the summer over a new contract for Liljegren. The Leafs had studied their trade options extensively and were disappointed in June, so they changed their commitment and gave Liljegren a surprise two-year deal for $3 million per season.

However, the contract was heavily frontloaded, with $2.4 million immediately paid out as a signing bonus. Liljegren was happy, but it was also a structure that would make the trade easier for him if it came to it.

It was another sign that the Leafs might not be committed to their longtime former first-rounder, who was selected a few regimes ago.

Liljegren viewed the deal as a vote of confidence and prepared for the season with a positive attitude. But then he played sparingly in preseason and ended up running with strange partners and groupings in training camp. Veteran Jake McCabe was also moved to right defense, blocking a potential role in the lineup, the opportunity Liljegren had been hoping for.

It was clear at the time that Craig Berube, the Leafs’ new coach, didn’t have him in his plans – unless there was a serious injury or something else unexpected. So Liljegren and his agent started thinking about other goals, and rebuilding the Sharks was high on their wish list, considering how many opportunities there would be for him to make big plays in all situations and perhaps take another step forward make.

That would obviously never happen in Toronto.

Liljegren leaves with mixed feelings. I don’t want to speak for him, but it must feel like unfinished business after pushing for so long to make the Leafs and secure a major role. But it’s also a chance to prove the Leafs wrong.

And simply getting out of a dysfunctional relationship.

“The way it went, he’s good (in the trade),” Wallen said. “Of course you’re always shocked when you get a call like that. (Before that) you’re mad and you want to get out (of Toronto) because you’re not playing. You wait, wait, wait, and then this call comes and you’re a little confused. There’s nothing strange about that.”

The big question in all of this for Toronto is: What is this player? What can Timothy Liljegren be?

He’s obviously one of the Sharks’ top four defensemen, but will he play there for a contender? Was there more that the Leafs didn’t realize after more than seven years of development, frustration and, yes, some progress? Were they wrong about him?

What was significant about all of this was that only a few teams called for Liljegren. How difficult the trade was. Utah, for example, lost two key right-backs for months earlier this season and still wasn’t particularly interested, opting for Olli Määttä instead.

Ultimately, at the end of October, only the Sharks remained as real applicants. What Treliving was able to get wasn’t much, but it felt like a victory considering he was moving a player who was still on the field, making $3 million and still had time left on the deal. A player who hadn’t established himself as an effective defender, who wasn’t trusted in the playoffs in Toronto and who made mistakes in crucial moments.

Liljegren’s underlying numbers always suggested there was potential for more, as the Leafs played an incredibly good game with him on the ice. He could move the puck, and when he was at his best, he could make anything look effortless. These moments and the analysis always earned him praise in some areas of this market.

If the hints of more pan out, if he finds his way and can play those big minutes on a good team, then maybe in two or three years we’ll be sitting here lamenting that the Leafs let a good player get away.

But the organization does not fear this outcome. It doesn’t expect it. This spring, the team is aiming for a push toward the championship, and the Leafs are fully committed to making that happen.

Six-foot-two Baltic miner Jani Hakanpää and his bad knee are poised to return to the lineup, likely this weekend, and he fits the mold that Treliving and Berube want these Leafs to have. That would never be Liljegren. He couldn’t do it.

The reality is also that the trade frees up valuable salary cap space for Toronto, backed by injured reserve and on the verge of clearing out the infirmary. Liljegren won’t be the only player to be released in the coming weeks. Some players have to give up, others are selected rather mediocre.

Benning adds another name to the mix, providing Toronto with nine defensemen on a temporary basis. A 30-year veteran who has battled injuries and moved around the league, he was a throw-in to the deal at the Sharks’ request, someone who could help make the money work.

At $1.25 million this season and next, Benning’s contract can be almost entirely buried in the AHL if he clears waivers. Or maybe the Leafs can get another deep pick in the next 48 hours from a team hungry for blue line help.

This is what the Leafs cap will now look like once everyone is healthy. They have three NHL players too many and will be over the cap by at least $1.7 million, so something else has to give other than finding a new home for Benning.

Maybe Philippe Myers will be waived, and maybe Benning too, jeopardizing some of the insurance they have behind Hakanpää, their wild card. At some point, once Calle Järnkrok is able to play again, they will also have to subtract a forward to meet the requirements, as no NHL team has 15 forwards for long periods of time.

Given this stalemate, it’s hard to argue that they’ll miss Liljegren at $3 million, with a coach who didn’t believe in him, especially given that he was a player who kept playing better, with confidence and a lot Time on the ice.

Wallen saw time and time again in Toronto how difficult it was, not just for his client, but for everyone. Losing in big games. The grind. The pressure on every play, especially as someone in the bubble fighting for a greater share of playing time when every mistake counted.

That’s one of the reasons they’re willing to give it up.

“It’s a tough market,” Wallen said. “It’s a very tough market for everyone. Coaches, GMs, players. It’s a challenging market… (It’s hard to play if you can’t build confidence) because you get a little hesitant. The league is so good today that you have to play with 110 percent confidence. It’s so fast. The pace is so intense today. You need to.”

Liljegren didn’t have that often enough in Toronto. Maybe it’ll come to San Jose?

But in hindsight, he was the wrong choice for the Leafs in 2017. They were also the wrong team for him.

And it feels like it’s always been that way.

(Photo: Paul Sancya / Associated Press)