Brian Cashman's Greatest Hits

Despite this disaster of a season in which the Yankees have gotten progressively worse by the month, are in last place, and need a good September to avoid finishing with a losing record for the first time in 30 years, it looks like Brian Cashman will be back as GM in 2024.  Even though Cashman is the one responsible for putting together this team, and the fact that this season really has been years in the making thanks to some of the questionable/disastrous personnel decisions he's made, that's evidently not enough for Hal Steinbrenner to make a change.

He's been the Yankees' GM for 25 years.  That alone should be enough to make you think a change could/should be in order.  Never mind the fact that this will be the 14th consecutive season without a pennant for a team that fancies itself a World Series contender every season.  Never mind the fact that he's obsessed with analytics for some reason, even though that approach has yielded zero results and Houston and Tampa Bay, the teams they're trying to emulate, aren't just better at it, they're better teams overall.

Anyway, Hal Steinbrenner has proven he's certainly not his father.  If George was still around and running things, Cashman would've been gone a long time ago.  There's been a lot of highs during his tenure.  No one's denying that.  But Cashman's misses have seemed to be piling up more and more in recent seasons.  And that's really why the team is in its current situation.

I don't even consider guys like A.J. Burnett or Giancarlo Stanton to be "bad" pickups.  Burnett was great in 2009, when he helped the team win a World Series, and Stanton has been exceptional when healthy.  He did almost single-handedly win the Division Series against the Rays in 2020.  I can't say the same about some other acquisitions, though.  Let's call them "Brian Cashman's Greatest Hits."

1. Josh Donaldson: Donaldson's Yankee career came to an unceremonious end when he was released on Tuesday.  They got him from the Twins along with Ben Rortvedt and Isiah Kiner-Falefa basically as a way of getting rid of Gary Sanchez, with Gio Urshela thrown in.  Needless to say, this trade did not work out well.  Donaldson wasn't good last year and was even worse this year.  IKF became a utility guy.  And Rortvedt got hurt in Spring Training, paving the way for Jose Trevino.

2. Aaron Hicks: Another guy Cashman got from the Twins, another guy who didn't work out.  Hicks was actually good when he first came over in 2016, but he needed Tommy John surgery right after signing a seven-year extension in 2019 and it's been downhill ever since.  Making matters worse, he knew he needed a left fielder, he knew Hicks sucked and he needed to unload him, and he did nothing about it.  Hicks started the season in New York and continued to be just as bad.  Cashman finally bit the bullet and released him in May.  The irony of the whole thing is that Hicks'll be the one who ends up in the postseason.

3. Frankie Montas & Lou Trivino: This may go down as his worst trade deadline acquisition.  Montas was awful as a Yankee.  Well, as it turns out, he was injured at the time of the trade and Oakland knew it.  How come Cashman didn't?  Montas hasn't pitched this season, no one has missed him, he'll leave as a free agent this winter, and no one will care.  Trivino, meanwhile, pitched in just a handful of games last season before needing Tommy John surgery.  It was a 2-for-1 deal.  One trade, two injured pitchers.

4. Clint Frazier: "Clint," "Jackson," whatever he wants to be called, "Red Thunder" was another swing and a miss.  He was supposed to be one of the big prizes of the 2016 sell-off that also landed Gleyber Torres (one of Cashman's few good trades in recent years).  Frazier came over from Cleveland for Andrew Miller, made his Major League debut in 2017, and spent most of the next four years on the injured list before he was finally designated for assignment in 2021.  Since then, he's played for three different organizations, bouncing between the Majors and Minors with the Cubs, Rangers and White Sox. 

5. Joey Gallo: Blaming this one entirely on Cashman isn't completely fair, since Yankee fans really wanted Gallo, too.  It went south almost immediately.  Gallo hit .160 with 88 strikeouts (in 188 at bats) in 58 games with the Yankees in 2021.  He was still re-signed for $10.275 million for 2022, yet somehow was even worse!  Gallo was hitting .159 and it was clearly getting to him when he was finally put out of his misery and sent to the Dodgers at the 2022 deadline.

6. Sonny Gray: For some reason, Cashman continues to make trades for Oakland pitchers even though they never work out well.  Before Montas and Trivino, there was Sonny Gray.  Gray made 11 starts after the trade in 2017 and went 4-7.  Then in 2018, he was so bad that he was demoted to the bullpen.  His Yankee Stadium ERA during his time in pinstripes?  7.71!  It was clearly just New York, seeing as Gray has made the All*Star team for both Cincinnati and Minnesota since he was traded to the Reds.

7. Carl Pavano: Getting Pavano for four years and $40 million actually seemed like a great deal at the time.  He was coming off an 18-8 season for the Marlins.  His Yankee tenure actually began pretty well, too.  Then Pavano got hurt.  And he spent pretty much the final three-and-a-half years of that contract on the injured list.  After missing the rest of 2005 and all of 2006, Pavano made a grand total of nine starts in 2007 and 2008 combined.

8. Michael Pineda: Pineda was traded to Yankees the winter after making the All*Star team as a Mariners rookie in 2011.  He didn't make his Yankees debut until 2012.  Two years of injuries before ever throwing a pitch for the team.  Pineda was actually solid in 2015, then went 6-12 with a 4.82 ERA and 27 home runs allowed in 2016.  Then in 2017, it was season-ending Tommy John surgery in July.

9. Stephen Drew: Remember when the Yankees and Red Sox randomly decided to make a trade with each other at the 2014 deadline?  I think they were both just trying to pull a fast one on the other by giving them someone they didn't want.  Kelly Johnson for Stephen Drew.  Drew hit just .150 with three home runs and 15 RBIs in 46 games for the Yankees after the trade, then played a full season with them in 2015 and hit a whopping .201!

10. Nick Johnson: Johnson's first tenure with the Yankees was oh-so-spectacular that Cashman just had to bring him back when he got the opportunity in 2010.  Despite the fact that he was a left-handed first baseman and they already had Mark Teixeira.  Not that it mattered.  Johnson started a grand total of 21 games (20 of them at DH) before hurting his wrist in May and, you guessed it, missing the rest of the season.

Not every trade or free agent signing is gonna work out.  Just like how sometimes you miss on a "can't miss" prospect.  This is an inexact science.  Everyone understands that.  But these doozies particularly stand out because of how spectacularly wrong they went.  And those failures have only been magnified by the team's coming up short of its annual World Series goal now 14 years in a row.

Can it all be blamed on Cashman?  Of course not.  He didn't acquire these guys knowing they were gonna suck.  He legitimately thought they'd make the team better.  But the bottom line is they didn't work out.  And these deals have helped put the Yankees on a path that has led to where they are now.  So, even if he doesn't deserve all the blame, he's ultimately the one responsible.