Buying out Benoit Pouliot, one of the team's best penalty killers, when we had more than enough cap space to fit in his 4 million=loss
Signing Draisaitl to 8.5 million, even though almost every single one of his similarly performing peers were signed for 1-2 million less=loss. It doesn't matter that Draisaitl is playing amazing. The issue is that basically any GM except Peter Chiarelli would have signed Draisaitl for less. But instead we are saddled with the worst GM at negotiating in the NHL.
Re-signing Eric Gryba for 2 years=loss. He's a coke machine who shouldn't dress in NHL games, and could probably have been retained with a PTO while he begged us to take him back since no other NHL team wants him. But no, the worst GM at negotiating in the NHL handed him a 2 year contract to reward him for blowing chunks last season. For his encore this season, continued to make use of his patented "Gryba fails to clear the puck out of the zone" move.
Kris Russell for 4 yearsx4 million=loss. There is just no justification for this contract whatsoever. But instead of doing his due diligence and trying to find the best possible fit for the Oilers, Peter "I'm so lazy I didn't bother to see what other dmen I could've gotten for Hall since I tunnel visioned for one player" Chiarelli decided that Kris Russell was the only fit for the Oilers and overpaid him to an extent that UFA was deemed unnecessary. No team was beating that offer for Kris Russell and everyone involved in the process, including Russell and Chiarelli probably, knew it.
Jordan Eberle for Ryan Strome isn't just a loss. It's a mega-loss. Not only does Chiarelli put the bowtie on one of the worst trades in NHL history by delivering Matt Barzal's ideal linemate to Garth Snow on a silver platter, the whole point of the trade was to make cap space, and he completely wasted that. If he'd used the 3.5 million saved from Eberle->Strome on good hockey moves, then I wouldn't be as pissed. Instead we hand Kris Russell a millstone contract, buy out Benoit Pouliot for no reason whatsoever, sign Draisaitl for more than every other one of his similarly producing peers, and worst of all, don't even make full use of that extra cap space. I mean we have 8 million cap space unused for Christ's sake, even if we account for McDavid, Pulju, Nurse etc's ELC bonuses, we still likely would have about 3.5 million left over. Perfect for just keeping our 30 goal scorer instead of trading him for a 30 point scorer.
Jussi Jokinen being a loss isn't the end of the world. Dude was a special kind of suck, but at least he does so for 1 year at 1 million. The problem is that Chiarelli brought him and Strome in and basically said to himself "I need no more work on the forwards" even though there were many clear holes that were yet to be addressed.
Matt Benning is not a win. Dude's been an inconsistent mess this year.
Auvitu is also not a win. Yeah he can contribute some offense and is not as frustratingly awful to watch as Eric Gryba. But his offense is not good enough to make up for the complete mess that his his defensive game and basically anyone can accomplish the latter.
Does Brandon Davidson really count as a win? He's been good for us. But keep in mind Peter Chiarelli traded him for the useless bum that was David Desharnais. The only reason we got the good Davy back was because Bergevin is even more incompetent than Chia as a talent evaluator, and Chia's own incompetence got us very high up the waiver priority ladder.