The first sign of trouble of Stan Bowman’s tenure was with the two offer sheets.

Shortly after joining the Edmonton Oilers, Bowman was faced with a dilemma: allow two young players to walk for a measly second- and third-round draft pick, or match their offers and go well over the cap and deal with that issue before the start of the season. Bowman chose the former, which turned out to be his first mistake as the general manager of the Oilers.

As you know, both players blossomed after joining the St. Louis Blues. Dylan Holloway, the 14th overall selection in 2020, scored a career-high 26 goals and 63 points in 2024-25, then added 22 goals and 51 points in 59 games last season. After scoring five goals and seven points in 25 games during the Oilers’ 2024 postseason run, his contract of a little under $2.3 million annually should have been matched.

Philip Broberg, the Oilers’ eighth overall selection from the draft prior, could never find footing on the Oilers’ backend. Upon joining the Blues, he scored eight goals and 29 points in 68 games, with a goal and two points in seven playoff games. Last season, he scored six goals and 34 points in 81 games, all while becoming a strong two-way defender.

In this trade tree, we’ll look at what the Oilers did with the assets they acquired as compensation for losing Holloway and Broberg.

The Philip Broberg portion of the tree

Broberg signed a two-year deal worth $4,580,917 annually. Any cent more than what he earned would have seen the Oilers receive a first and a third. But since the Blues signed him at that price point, the Oilers essentially got a second for Broberg.

That second wasn’t used by the Oilers, as it was packaged alongside prospects Max Wanner, Shane Lachance, and a 2026 fourth for Trent Frederic with 75 per cent retention, Max Jones, and Petr Hauser.

In turn, the Bruins used that pick to select centre........

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