Pretty much every Major League Baseball team regrets something it did or did not do at the trade deadline on August 2.

But some of those regrets are bigger than others.

Could the New York Mets and Chicago White Sox have done more to improve their rosters ahead of the deadline? Absolutely. But their crosstown rivals are on this list for two trades that haven't panned out (Yankees) and a non-trade that never made sense to any of us (Cubs).

For the most part, we'll be focused on teams that at least had a postseason pulse when the deadline hit. However, we'll start out with a team that didn't even have a realistic shot at the playoffs on Opening Day.

And we'll wrap things up with my biggest regret from the trade deadline.


Oakland A's: Not Trading Away Elvis Andrus and Sean Murphy

The Elvis Andrus part of it I can understand, as there probably weren't many suitors for a $7 million 33-year-old shortstop with minimal pop and a sub-.300 on-base percentage dating back to the start of 2020. Didn't help matters that his contract included a $15 million player option for 2023 if he reached 550 plate appearances this season, which he was/is roughly on pace to do.

But they surely could have gotten something for him if they were willing to eat the rest of his 2022 salary just to have him play somewhere else—which they were clearly willing to do, because they designated him for assignment two weeks after the trade deadline. The Chicago White Sox scooped him up for basically nothing and he has been thriving in Tim Anderson's stead, batting .308 with six home runs.

The Sean Murphy part is less understandable, because he is clearly a player with a lot of value which the A's could have turned into prospects—which has more or less been their entire goal for the past calendar year of rebuilding.

The 27-year-old catcher is making $725,000 this season and is arbitration-eligible through each of the next three seasons. And he's quite good. He hit 17 home runs and won a Gold Glove last season. This year, he's batting .253 with 18 home runs. He's clearly a player any team actually trying to win baseball games would love to have under its control through the end of 2025.

At any other position, it would make sense for the A's to just hang onto this asset and hope to become competitive again before he hits free agency. But, per's prospect rankings, three of the top five players in Oakland's farm system are catchers. And they even called up the top guy on that list, Shea Langeliers, when they waived Andrus.

Selling Murphy for a platter of prospects was the obvious move here, and it became an even bigger whiff by Oakland when the Cubs ended up not trading Willson Contreras. Murphy would've been the best backstop available and would have been quite valuable on the trade block.