It's a rarity in the NHL when a player signs an offer sheet, let alone an offer sheet that isn't matched by another team. To think that the St. Louis Blues agreed to offer sheets with Dylan Holloway and Philip Broberg, both of whom were current Edmonton Oilers players, is unheard of. 

When the offer sheets were signed, many fans assumed that Broberg's contract wasn't likely to be matched, but Holloway's relatively low cap hit would. Shocking everyone, the Oilers elected to let the duo leave, receiving draft picks as compensation. 

The move paid off for GM Doug Armstrong and the Blues, as Broberg and Holloway had breakout seasons, playing critical roles in their playoff berth.

Unfortunately for the Blues, Holloway suffered an injury prior to the playoffs and didn't appear in their first-round matchup against the Winnipeg Jets. Recently, he was on the Cam and Strick Podcast and discussed the severity of the oblique injury he suffered.

He also talked about the situation between him and his former team, and how the Oilers' treatment towards him during the contract negotiations rubbed him the wrong way. 

"It rubbed me the wrong way how little Edmonton thought of me in our contract negotiations… I’m an Alberta boy; I wanted to go back to a team we went so far with, but as soon as Edmonton didn’t reciprocate that feeling, I was all in on St. Louis," Holloway said.

Although the Oilers ultimately had a better season than the Blues, losing in the Stanley Cup finals to the Florida Panthers for the second consecutive season, the absence of Broberg, and especially Holloway, could have cost the Oilers a Stanley Cup.

They lacked scoring options outside of Connor McDavid and Leon Draisaitl, and when Zach Hyman went down with an injury, they were desperate for another player to step into a top-six role. Holloway's breakout campaign shows just how valuable he could have been for that Oilers squad.

With that being said, Holloway is in a new city, with a different environment, one that he has already thrived in. The expectation is that Holloway takes another step forward in the 2025-26 season.