December 16, 2025 by Eric Friesen

There’s always plenty of interest whenever the Edmonton Oilers and Pittsburgh Penguins have clashed over the past decade, because of the rare opportunity to see generational talents Connor McDavid and Sidney Crosby share the same sheet of ice.

In head-to-head 15 contests, McDavid has nine goals and 30 points and the Oilers hold an 8-4-3 record, while Crosby has four goals and 10 points and the Penguins own a 7-7-1 record. That will undoubtedly still be the focus of many hockey fans as the Penguins prepare to host the Oilers at PPG Paints Arena on Tuesday.

However, for the first time in the McDavid era, it won’t be the biggest headline-maker in a game featuring the two soon-to-be Canadian Olympic teammates. After weeks of trade speculation between the clubs, the Oilers acquired goalie Tristan Jarry and forward prospect Samuel Poulin from the Penguins in exchange for Stuart Skinner, Brett Kulak and a second-round pick in the 2029 NHL Draft on Friday.

Jarry stopped 25 of 28 shots to secure a 6-3 victory over the Toronto Maple Leafs in his Oilers debut on Saturday, while Skinner and Kulak are set to make their first appearances with the Penguins against their hometown team that just traded them four days ago. Facing your old team for the first time is bound to bring on a mix of emotions, excitement and pressure to perform well, but for it to happen in your first game with a new team could only amplify everything for the players involved.

The Skinner-for-Jarry trade is eerily similar to when the Oilers dealt Esa Tikkanen to the New York Rangers for Doug Weight on March 17, 1993. Weight quickly packed up his gear and sticks and moved down the hallway to the visitors’ dressing room at Madison Square Garden, as the Oilers were in Manhattan to play the Rangers that night.

Jarry, who spent his entire WHL career with the Edmonton Oil Kings and the better part of a decade with one team in the NHL, expressed the strange feelings that come with being trade for the first time.

“It’s obviously been crazy,” Jarry told Oilers TV on Monday. “I’ve never been a part of anything like that, so it’s obviously all new. Going from one team to the next and then playing the next day, it’s obviously a lot of emotions. Putting on a different jersey for the first time was a little weird, but I’m obviously very excited [to be an Oiler].”

Though he only appeared in one game with the Penguins when he broke into the league in 2016-17, the organization still gave Jarry a Stanley Cup ring for his contributions that season. Jarry went to become the No. 1 netminder in Pittsburgh, but he’s only started eight playoff games during his 10-year NHL career. The 30-year-old goalie is now tasked with backstopping the two-time defending Western Conference champion Oilers to their ultimate goal of hoisting the Cup in June.

“It’s obviously fun [to be joining a Stanley Cup contender], said Jarry. “There’s a huge following for the team, and I think with everything that comes with the team is a different challenge.”

While the team and the player were both clearly in need of a change, Skinner leaves Edmonton as one of the most accomplished goalies in franchise history. Skinner ranks fifth in wins (109), tied for fourth in shutouts (9), tied for seventh in goals against average (2.74), tied for 10th in save percentage (.904), sixth in games played among goalies (197), second in playoff wins (26), second in playoff shutouts (4), sixth in playoff goals against average (2.88) and second in playoff games played among goalies (50).

The Edmonton native was named to the 2022-23 NHL All-Rookie Team, he played in the 2023 NHL All-Star Game, and most notably helped the Oilers make consecutive Stanley Cup Final appearances in 2024 and 2025.

“There’s been a lot of noise, obviously. There’s a lot of noise around goalies,” Skinner said in his media availability on Tuesday. It’s a trade that needed to be done, and I think it’s good for both teams.

“For me, I’m very proud of what I was able to do [in Edmonton]. Could I have made an extra save or two? Absolutely. I’ll probably say that [in Pittsburgh], but that’s kind of part of being a goalie and being a person. But I always did my best, and I will never stop doing my best.”

While most of the discussion has been surrounding the goalie swap, Kulak also played an important role on the back end for the Oilers’ two Cup runs. The 31-year-old played in every regular season and playoff game during his time with the orange and blue, and routinely stepped up his game at the most important time of the year. Despite how different this game will be for everyone involved, Kulak insists it feel like any other game.

“Right now it feels just like a normal game day,” said Kulak after the Penguins’ morning skate on Tuesday. “But I guess I’ll have to see how I feel once we get on for warmup and I look across the ice and see my old teammates.”

In addition to all of the extra attention on Jarry and Skinner opposing each other between the pipes, Leon Draisaitl and Crosby are both on the verge of making history. Draisaitl needs just one point to become the fifth player in Oilers history and the fifth-fastest European-born player in NHL history to reach the 1,000-point plateau. The German superstar is also two goals away passing Glenn Anderson for the third-most in franchise history (418).

Meanwhile, Crosby is just three points away from passing Mario Lemieux for eighth on the NHL all-time points list (1,723) as well as becoming the Penguins’ all-time points leader. The 38-year-old future Hall of Famer surpassed Joe Sakic for ninth when he last faced the Oilers (and Stuart Skinner) in Pittsburgh just under a year ago.