On Monday, the Toronto Maple Leafs officially announced John Chayka as their new general manager.

Chayka, now a 36-year-old executive, was formerly the general manager of the Arizona Coyotes. He was the youngest general manager in NHL history upon landing in the desert in May of 2016.

After nearly half a decade away from the league, he’s now back and working in a much, much bigger market. The early days are not going over well in Toronto. Local media has lambasted the organization for hiring him, his introductory press conference was filled with uncomfortable questions, and the fan base is, at absolute best, highly skeptical.

It’s not without merit. Though Chayka’s checkered résumé includes a questionable trade and draft record, a decent amount of the dislike surrounding his hire comes from the way his tenure in Arizona.

Months after he abruptly left the Coyotes right before the start of the 2020 Stanley Cup Playoffs, he was suspended from the league for “conduct detrimental to the league” after he was in discussions with the New Jerset Devils about a job. After his departure, the Coyotes were also fined draft picks for illegally hosting a private scouting combine for prospects, forbidden by the NHL.

Whether this is ultimately a good hire is for time to decide, and for how the folks in Toronto feel, I’ll direct you north of the border to find that out.

But since Chayka is back in the spotlight, I figured it would be fun to take a look at one of the big trades Chayka made with the Pittsburgh Penguins back when he was in charge in Arizona.

The Trade

A week after the 2019 NHL Draft, Penguins general manager Jim Rutherford undid one of the biggest moves he made to assemble a back-to-back Stanley Cup-winning roster.

On June 29th, the Penguins traded winger Phil Kessel, along with 23-year-old minor league defenseman Dane Birks and a 2021 fourth round pick to Chayka’s Coyotes in exchange for forward Alex Galchenyuk and 19-year-old prospect defenseman Pierre-Olivier Joseph.

The trade left the Penguins with a little more than $3 million in cap space, exchanging Kessel’s $8 million cap hit for Galchenyuk’s $4.9 million, amidst other assets.

Kessel and Rutherford publicly clashed as to the reason his time with the Penguins came to an end, and the player had reportedly nixed a trade to Minnesota, voicing his desire to play for former Penguins assistant head coach Rick Tocchet in Arizona.

But this was a massive trade for the Penguins at the time. Kessel had recorded 110 goals and 303 points in 328 regular season games (four straight 82-game campaigns), and another 20 goals and 56 points in 65 postseason games.

The trade also cast both teams in unusual roles. Rutherford’s Penguins almost never “sold” a player, and Chayka’s Coyotes had rarely landed the headline player in the deal (at least up until then).

Ultimately, however, despite some of the big names involved in this trade, it underwhelmed for both sides.

The Pittsburgh Side

The NHL-ready piece arriving in Pittsburgh from the Chayka system was Alex Galchenyuk, a forward who despite being just 25 years old had seven seasons of experience in the league.

Galchenyuk was the third overall pick by the Montreal Canadiens back in 2012, a draft held in Pittsburgh. He made the team that following season, and after six years in Montreal, was acquired by Arizona in a one-for-one with Max Domi.

Galchenyuk’s one year in Arizona saw him saw him record 41 points in 72 games. That’s not a bad figure, but it was his lowest point total since his sophomore year.

“We like Alex,” Rutherford said at the time. “We know he can score when he’s on the top of his game. He’d already done it. He’s had a 30-goal season.”

But despite Rutherford’s public praise for the forward, there was concern about how he would fit into the lineup for the Penguins. A natural center during his stops in Montreal and Arizona, Galchenyuk was shifted to wing to set him up with a top-six spot.

But his style of play clashed with that of Sidney Crosby and Evgeni Malkin, a problem Tocchet reportedly had warned Penguins head coach Mike Sullivan about after the deal.

The Coyotes head coach was right; Galchenyuk could never find a fit in Pittsburgh. He took 15 games to score his first goal in 2019-20, and although Galchenyuk was half a point-per-game through his first 20 with the Penguins, extended cold streaks left him with just five goals and 12 assists (17 points) in 45 games.

Weeks before the trade deadline, he was moved to Minnesota along with prospect defenseman Calen Addison and a first-round pick in 2020 for Jason Zucker, the winger Rutherford originally wanted for Kessel.

Galchenyuk, who was in the final year of a three-year deal, did not stay in Minnesota. He bounced around the NHL over the next three seasons, including a reunion with the Coyotes in 2021-22. He has not played in the NHL since the 2022-23 season.

The Penguins also made the rare move of acquiring a prospect in the Kessel trade. P.O. Joseph, as he would come to be known in Pittsburgh, was just two years removed from being the 23rd overall pick in the 2017 draft by the Coyotes.

At the time of the trade, Joseph had wrapped up his final season of junior hockey in the QMJHL. The left-shot defenseman was a captain of the Charlottetown Islanders for a year and a half and was ready to make the jump to pro for the 2019-20 season.

Joseph took a few seasons to fully hit his stride in the NHL, not uncommon for a developing defenseman. He played 16 games for the Penguins in his second pro year, taking advantage of a depleted blue line in that wacky 2020-21 Covid year.

His best season with the organization was the 2022-23 season, when he finally snagged a full-time job in the NHL and appeared in a career-high 75 games with 21 points and a +8 rating.

Though he stuck around in the organization far longer than Galchenyuk did, Joseph was primarily a depth defenseman for the Penguins. Pittsburgh opted not to qualify the restricted free agent in 2024. They did have a reunion with him that fall, but he once again was allowed to walk last offseason.

In total, the Penguins got 216 games of service and 57 points out of Kessel’s direct acquisition. Yes, they pawned Galchenyuk into a more productive winger in Zucker, but it was a deal that most would say fell flat for Rutherford.

The Arizona Side

Chayka was thrilled to acquire a forward with Phil Kessel‘s pedigree, and his relationship with Tocchet.

“Toch knows him extremely well and coached him and he knows exactly what he’s getting with Phil, and Phil knows exactly what he’s getting with Toch,” Chayka said at the time. “All this gives us comfort we’re not only getting a Stanley Cup winner and an elite scorer, but a guy who should fit in well and come in motivated.”

The Coyotes were not only looking for a veteran forward to help round out their lineup, but someone who could help bring along some of the forwards Chayka wanted to develop.

“We felt we needed a lead horse up front, a guy who’s produced offensively consistently,” he said. “We were looking for a veteran player who has a history of doing it. We have a lot of players who have a lot of upside and potential, but we needed a player who could be a 20 or hopefully 30-goal scorer.”

The Coyotes were coming off their best season since the 2013-14 campaign. In 2018-19, Arizona had also made a ten-win, 14-point improvement over the season before. Despite those steps towards a more competitive club, the Coyotes lacked some serious offensive power. Kessel’s 82 points in 2018-19 would have almost doubled team leader Clayton Keller’s 47 points.

But upon arriving in Arizona, Kessel struggled to make the impact Chayka hoped for. He got off to a hot start with ten points in 15 games, but ultimately underwhelmed with 14 goals and 24 assists (38 points) in 70 games.

Despite the lack of offense in Arizona yet again, the Coyotes were still a competitive club. Chayka, feeling bold after the Kessel trade, made another big swing near the trade deadline to acquire Taylor Hall, who was less than two years removed from a Hart Trophy win as league MVP.

Hall and Kessel became the de facto leaders up front for a Coyotes team that were in fifth place in the Pacific Division at the time of the Covid pause. When the league resumed in August, Arizona secured an invite to the 24-team tournament happening in the bubbles in Canada.

Chayka left the team before those playoffs started. The abandoned Coyotes knocked off Nashville 3-1 in the qualifying round before falling in five games to Colorado. Kessel had four points in nine games.

Kessel did rebound somewhat in his next two years with the Coyotes, rallying for 20 goals and 23 assists (43 points) in 56 games during the 2020-21 season. The following year, Kessel put up his only single-digit goal total in the NHL, but racked up 44 assists for a 52-point campaign.

Upon his contract expiring, new management in Arizona let him walk. He signed for one year in Vegas, putting up a 34-point, 82-game campaign in his final year in the NHL.

Kessel was the only player of NHL impact the Coyotes received in the deal. Dane Birks, the defensive prospect they received, spent the 2019-20 season in the ECHL with Arizona’s affiliate, the Rapid City Rush. He returned to Pittsburgh’s ECHL affiliate in Wheeling the following year, his last in hockey.

That fourth round pick Arizona acquired was used by Chayka’s successor in Bill Armstrong to draft Rasmus Korhonen, a Finnish goaltender at 122nd overall. Korhonen played five games for the AHL’s Tucson Roadrunners in the 2021-22 season, but has otherwise exclusively played in the Finnish and Swedish leagues.