In terms of unforced errors, the debacle that has been Trent Frederic's career with the Edmonton Oilers has few comparables. An overpayment at the trade deadline, for an injured player, led to a single playoff goal. The Boston Bruins were offloading talent, and when all was said and done, the hero of the Stanley Cup Finals, Brad Marchand, went to the Florida Panthers for virtually the same price as the Oilers paid for Frederic.
Rather than accepting sunk cost and moving on, Oilers general manager Stan Bowman remained so certain he'd won that trade, that he signed Frederic to an eight year, $30.8 million contract. Elementary children will be graduating high school when Frederic's contract is up. And if the Oilers were to contemplate a buyout, most of the current roster will be retired when the payments end (in 2040!).
Look at who isn't buying players out
The two clubs battling it out in the Western Conference Final, the Colorado Avalanche and Vegas Golden Knights, have zero dollars in dead money on their rosters. The two-time Stanley Cup Champion Florida Panthers also have no buyouts counting against their cap. The Carolina Hurricanes have a paltry $883k, and perennial favorites, the Tampa Bay Lightning, also haven't bought anyone out.
It would be a stretch to say that these clubs haven't made any poor signings or trades. But it seems clear that their management teams see the arms race at the top of the league, and recognize that every available dollar counts when it comes to adding key pieces for a postseason run.
Oilers haven't had a full cap available
Somebody has been paid not to play for Edmonton in virtually every year of Connor McDavid's career. That means that a gallery of GMs haven't had the same available dollars as their opponents, and yet each successive manager has chosen to continue the trend. From Lucic/Neal, to Andrej Sekera, to Jack Campbell, there has always been a poorly considered deal limiting cap flexibility.
We can look at the dual offer sheets given to Philip Broberg and forward Dylan Holloway as an example of how previous mistakes affect the present. The Oilers were up against the salary cap, owing performance bonuses to a number of players, and they had Campbell's buyout on their cap. Those combined factors meant the St. Louis Blues saw an opportunity to snipe two talented young players off Edmonton's roster, and the resulting gap in depth surely played a role in the team's decline since those offers were signed.
Other top teams find creative solutions to these problems. On the extreme end, the Lightning and Golden Knights actually found ways to significantly exceed the salary cap in recent years, and while the NHL might be closing existing loopholes, the best management teams are always looking for new ways to bend the rules in their favour. We haven't seen much to suggest that the Oilers have one of the league's "best" management teams in any recent season, and each successive GM's lack of originality merely passes problems on to the next guy. Hopefully Stan Bowman sees the math.
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