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Penguins re-sign Drew O’Connor, start clock on last best chance to acquire Erik Karlsson

The Pens sign their last restricted free agent, but the story behind the story looms larger at this moment

NHL: Montreal Canadiens at Pittsburgh Penguins Charles LeClaire-USA TODAY Sports

The Penguins announced today that they have re-signed Drew O’Connor to a two-year contract.

From the team:

The Pittsburgh Penguins have re-signed forward Drew O’Connor to a two-year contract, it was announced today by President of Hockey Operations Kyle Dubas.

The deal runs through the 2024-25 campaign and carries an average annual value of $925,000.

O’Connor, 25, split the 2022-23 season between Pittsburgh and the Wilkes-Barre/Scranton Penguins of the American Hockey League. With Pittsburgh, O’Connor had his best NHL season to date, setting career highs in games played (46), goals (5), assists (6), points (11) and hits (63). With WBS, the 6-foot-3, 200-pound forward recorded 22 points (8G-14A) in 20 games and was a plus-9.

The Chatham, New Jersey native represented his native country for the first time at the 2023 IIHF World Championship. With Team USA, O’Connor notched three goals, five assists and eight points in 10 games. His three goals and eight points each ranked fourth on the team.

O’Connor has played parts of three seasons in the NHL, all with Pittsburgh. In 78 career regular-season games, he has recorded eight goals, nine assists and 17 points. O’Connor has also spent parts of three seasons with WBS recording 27 goals, 46 assists and 73 points in 73 career AHL games.

O’Connor is a nice piece of the puzzle who has worked his way up the organization from an undrafted free agent to what should be becoming a piece of the NHL puzzle for the next two seasons with that contract.

But the bigger story is what this signing means. O’Connor getting wrapped up after filing for arbitration means that the Pens get an extra buyout window, with some conditions attached.

This buyout window that begins on Saturday morning in 72 hours from now, offers the last best chance to clear up salary cap space that would be necessary to open room to acquire Erik Karlsson.

Dubas has indicated a strong preference to want to avoid usage of any buyouts, which will tack on extra penalty years to the team’s cap situation. The buyout penalties for Jack Johnson, for instance, who was cut back in 2020 are only halfway over and linger with a penalty to the Pens through 2025-26, for one example of how long those things can last.

On the other hand, Dubas hasn’t been able to make any magic by parsing big salaries via trade — for the obvious enough reason that few teams even have the space to absorb a big cap hit like Mikael Granlund or Jeff Petry. Buying out players like that (especially with Petry’s no trade clause) could be the only way to ensure dumping them.

Of course, this action to re-sign O’Connor ahead of his weekend arbitration case could also be the throwing in of the towel and admission that the money and trade ask of San Jose just isn’t going to be workable for the Penguins at this time. As such, if the buyout window comes and goes this weekend without any further action, is Pittsburgh out of the Erik Karlsson derby? Perhaps not 100%, but if answers and movement isn’t coming soon, the lack of answers/movement could well be an answer in and of itself.