Erik Karlsson’s time with the Sharks — a sometimes electrifying but all-too-often disappointing five-year period in which the team made only one playoff appearance — came to an end Sunday as the three-time Norris Trophy winner was traded to the Pittsburgh Penguins.

Completing one of the biggest trades of his brief tenure as Sharks general manager, Mike Grier sent Karlsson, forward Dillon Hamaliuk, and San Jose’s 2026 third-round NHL draft pick to the Penguins for Pittsburgh’s 2024 first-round NHL draft pick, forward Mikael Granlund, forward Mike Hoffman, and defenseman Jan Rutta.

San Jose will also retain $1.5 million on Karlsson’s contract for the next four seasons, approximately 13.04 percent of the defenseman’s $11.5 million annual salary cap hit. If Pittsburgh’s draft pick in 2024 is in the top 10, Pittsburgh can elect to transfer that first-rounder to 2025.A third team, Montreal, was involved, as Hoffman went from the Canadiens to the Sharks. In the deal, the Canadiens acquired Pittsburgh’s 2025 second-round draft pick, defenseman Jeff Petry, goaltender Casey DeSmith and forward Nathan Legare. The Penguins are retaining 25 percent of Petry’s $6.25 million annual salary cap hit.

The trade ends months of speculation as to where Karlsson, the first defenseman to be traded after winning the Norris Trophy since Doug Harvey in 1961, might play next season.

Grier said he and Penguins GM Kyle Dubas talked multiple times over the last several weeks to try and hammer out an agreement.

“It’s been kind of a long grind throughout not only the regular season but the summer to get this done,” Grier said Sunday. “We’ve been going at it for a while trying to get this done with a few teams. Kyle’s been pretty up front and aggressive for the last couple of months, but it’s been a little bit of a grind.”

Granlund, 31, had 41 points in 79 games last season as he played with both Nashville and Pittsburgh. He has two years remaining on a four-year, $20 million deal he signed with Nashville in 2021.

Hoffman, 33, had 34 points in 67 games with the Canadiens last season and is entering the final year of a three-year, $13.5 million deal.

This is actually the second time Hoffman has been on the Sharks’ roster. In June 2018, the Sharks acquired the forward from Ottawa in a multi-player trade, then, shortly afterward, sent him to Florida for draft picks.

Rutta, 32, had nine points in 56 games for Pittsburgh last season. He has two years left on a deal that carries a cap hit of $2.75 million per season.

The Sharks, per CapFriendly, now have just under $4 million in cap space for next season. But the true benefit to the Sharks was freeing up an additional $10 million in cap space for the following three seasons, giving Grier more flexibility to reshape the roster.

“There were teams asking us to retain a lot of salary, and it was something we really didn’t want to do,” Grier of Karlsson’s contract. “We wanted to be able to have some cap flexibility and financial flexibility to add players down the road that fit what we wanted to do.”

Since coming to the Sharks close to five years ago, Karlsson had 243 points in 293 regular-season games. But after missing the playoffs each of the last four seasons with the Sharks, which included a dismal 22-44-16 record this past year, Karlsson, 33, sought to play for a Stanley Cup contender once again.

Karlsson’s contract contained a full no-movement clause, giving him some control in terms of where he would play next. He confirmed last month that he had been in talks with Dubas and the Penguins.

“I could go through 82 games a year and be good,” Karlsson said on June 25, the day before he won his third Norris Trophy, “but I want to play when it matters.”

Grier wanted to accommodate Karlsson’s trade request but also needed a return somewhat commensurate with the player’s value. Since Karlsson entered the NHL in 2009, no defenseman has scored more points (761) and only three more have averaged more ice time per game (25:29).

This past season, Karlsson had 25 goals and 76 assists as he became the first NHL defenseman in 31 years to score more than 100 points.

Still, trading Karlsson and his cap hit for each of the next four seasons figured to be difficult.

The NHL’s salary cap is increasing by only $1 million to $83.5 million for the upcoming season, and Grier made it clear last month that the Sharks were only willing to retain so much of Karlsson’s contract — certainly less than the 50% maximum allowed by the collective bargaining agreement. But even at a reduced cap hit, only a handful of contending teams had the space needed to absorb Karlsson’s contract.

Grier said team owner Hasso Plattner remained involved throughout the process.

“We went through this whole thing together and we decided that the best path forward was to maintain that financial flexibility down the road,” Grier said.

The Sharks now turn the page on the Karlsson era — one that began with hopes that the dynamic defenseman could help bring the team their first championship.

In a Cup-or-bust blockbuster trade made on Sept. 13, 2018, Karlsson was acquired from Ottawa for four players and three draft picks.

At his best in San Jose, Karlsson was a one-man breakout machine with playmaking skills possessed by few other NHL defensemen. His Sharks teammates often just had to get open before Karlsson, using his elite vision and passing ability, would slide the puck right on their sticks.

“You can’t replace Erik Karlsson. He’s one of a kind, in my opinion,” Sharks captain Logan Couture said in April.

Karlsson had 45 points in 52 regular-season games for the Sharks in 2018-19 but injured his groin in January and missed 27 of the team’s final 33 regular-season games. Karlsson then played 19 of 20 playoff games as the Sharks lost in the Western Conference finals to the eventual Cup champion St. Louis Blues.

Karlsson had groin surgery on his 29th birthday on May 31, 2019, and less than three weeks later, was signed by the Sharks to an eight-year, $92 million contract, making him the NHL’s highest-paid defenseman.

The Sharks’ overall fortunes then went downhill. Fast.

Karlsson’s injury woes continued as various ailments forced him to miss 50 of the next 208 regular-season games between 2019-2020 and 2021-2022. A lack of depth, caused in part by Karlsson’s contract, and those awarded to Couture, Brent Burns, Marc-Edouard Vlasic, Evander Kane, and Martin Jones, and a mostly flat salary cap, started a tailspin in which the Sharks won just 82 of those 208 games.