Bad moves:
Opted to let Freeman walk only to trade valuable assets to Oakland for another 1b and pay him the same contract Freeman wanted. Freeman and Olson have been worth roughly equal value, but Shea turned into a 3-4 WAR Catcher. This move wasn't completely terrible, but it was a bad decision nonetheless, especially with hindsight.
Let Swanson walk after 2022 and hasn't found a suitable replacement in 3 years.
Letting Fried walk last year and not finding ANY sort of replacement
Murphy trade was bad at the time and awful now. Then failed to trade him away last deadline when he would brought back a haul.
JK trade was awful and hindered our ability to improve the club later
Signed Eddie Rosario multiple times over the last 4 years
Traded for Soler and his bad contract in 2024.
Guaranteed the final year of the Lopez contract after his 2024 season, instead of letting it be an option year.
DFA'ing Griffin Canning and Ramon Laureano last off-season when our needs going into the season were (checks notes) pitching depth and a solid hitting LFer.
Signing Profar when we already had a DH
Bummer contract (nitpicking here, but 9.5 million for 2026 is a little ridiculous for a mediocre middle reliever)
And obviously the not doing anything is a bad move when you have obvious holes
VS the good moves he has made:
Sale (granted, this was an amazingly good move)
Iggy
Jansen
Holmes
Laureano (before DFAing him)
Lopez (before the final year guarantee)
Pierce Johnson
I might give him partial credit on the good side for Olson since he has been pretty great.
Most of his good moves have been relievers.