Yankees’ trade woes, on-field struggles are in the making for many years


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Out of all the 30 MLB teams, the Yankees were the last ones to make a trade at this deadline. It seems like they did it partly to avoid the embarrassment of being the only team that didn’t make a trade. Their “big” move was to get a middle-of-the-road relief pitcher named Keynan Middleton from the White Sox. They also got the contract of Spencer Howard, who was once a promising pitching prospect, from the Rangers but intended for Triple-A only. However, Howard has had a tough time in his four seasons, with a high ERA of 7.20.

The problems they’re facing in the AL East and their struggle to make important decisions like buying or selling players, or making moves that could help this year’s team or future Yankees teams succeed, are the result of a mix of strategies that didn’t work and the way they acquired players over many years. This wasn’t just about the trade deadline in 2023.

Middleton is having his best year with a much higher rate of strikeouts at 30.1%. However, he’s not particularly good against left-handed or right-handed batters, and he’s more likely to give up home runs. When he comes back from the injured list, he will be ranked lower than Clay Holmes, Michael King, Wandy Peralta, Tommy Kahnle, Ian Hamilton, and Jonathan Loaisiga in the Yankees’ bullpen order.

Therefore, the Yankees got a relief pitcher who would be ranked seventh in importance. Depending on how you view Nick Ramirez and the recently moved-down Ron Marinaccio, he might even be ranked eighth or ninth. This is something the Yankees are typically good at currently – making the most of bullpen pitchers. They might be able to do the same with Middleton and Howard.

Yankees ignored the glaring disorder

However, they are at the bottom of the AL East when it comes to problems in other areas, especially in their batting order. They had a lot of trouble in left field and at third base last year. They didn’t try to fix these issues during the offseason, and they still haven’t. Unless they can use some magical solution like Bugs Bunny, where Aaron Judge can be in every batting position, from leading off to hitting second and third, it’s hard to see how things will get better. And this isn’t just about this year.

Yankees first baseman Anthony Rizzo is arguing with umpire during the game against the Orioles at Camden Yards.

DJ LeMahieu, Anthony Rizzo, and Giancarlo Stanton, who now seem more suited for a place like Jurassic Park than Yankee Stadium, are all part of the team next year. Only the Yankees may be hoping these players will get better, especially since they were slow to realize that Josh Donaldson’s drop in performance in 2022 wasn’t just a one-time thing.

But the management’s attitude and trade behavior indicate that the Yankees were stuck. They were in a position where they didn’t want to give up on reaching the wild-card spot in 2023. However, the actual outcomes of their games made it clear that investing in their top young players to improve the team wasn’t the best idea. This was especially true since they didn’t have a surplus of highly promising young players to spare.

They were trying to do something tricky: trade away a player like Harrison Bader, whose contract ends soon, to get something valuable for the future. At the same time, they wanted to use young players to fix the issue in left field, both now and in the future. However, in the end, they ended up getting two more relief pitchers instead.

Problems galore for the Yankees

This problem wasn’t just about August 1, 2023. It was about dealing with ongoing problems that were becoming more difficult to handle, even though the Yankees kept making it to the playoffs. It’s possible that they might make it to the playoffs again this year, but the owner, Hal Steinbrenner, General Manager Brian Cashman, and the baseball operations team should realize that their current direction is leading to a troublesome situation – and it might even be there already.

Explaining thoroughly why the team with the second-highest salaries was only hitting .230, ranked 21st in runs per game, and had Jake Bauers, a player who hasn’t been very famous, as one of their most important hitters after Aaron Judge, would require a long explanation, almost like reading a book.

Yankees GM is explaining his trade inaction while fan Jon holds a banner reading "FIRE CASHMAN" outside Yankee Stadium on Aug 1, 2023.
Twitter/ @JonFromMaspeth

However, there have been draft picks that didn’t even lead to players who performed at an average level. The international market also hasn’t brought in players like Juan Soto, Ronald Acuna Jr., or Wander Franco. Additionally, players like Greg Bird, Gary Sanchez, Miguel Andujar, and Clint Frazier had their performances drop significantly, yet the team held onto them for too long even after they weren’t performing well anymore.

The team stubbornly stuck with a strategy of having more right-handed players and didn’t pay enough attention to reducing strikeouts. This approach failed repeatedly in the playoffs, and it also made the team lack different types of players and the ability to move swiftly, which is crucial, especially now.

They made several bad trades where they used up their promising young players on players like Joey Gallo and Frankie Montas. Even though they were in first place before the last deadline, they made bold moves to bring in five players, but it didn’t make a big difference. The outcome was similar to what they’ve experienced before – they easily won against a weaker AL Central team in the early playoffs but got eliminated by a team that’s just better overall at playing baseball, usually the Astros. After that, they still believed that their team was very close to winning everything.

Last year, the Yankees spent more during the trade deadline because four players were part of the team until 2024. However, things haven’t gone well. Harrison Bader has been on the injured list two times, and Montas, Scott Effross, and Lou Trivino haven’t played at all. This is a big failure, similar to thinking Isiah Kiner-Falefa could be a good shortstop and agreeing to pay $50 million for Donaldson, but it didn’t work out as planned.

It is not possible to keep having so many failures in different areas and think that the money, especially the good investments in players like Judge and Gerrit Cole, will hide all of the problems. All these issues led to a trade deadline where the Yankees pretty much stayed where they were. Maybe not making many moves is actually a good thing – it would have been better last year too.

However, they didn’t want to stay inactive. They were forced into this inactivity because of everything that happened leading up to August 1, 2023. They couldn’t make the 2023 team better, and they also couldn’t plan well for the future. Instead, they brought in a reliever who is not considered very important and a player who used to be promising but hasn’t lived up to it.

This was a day that had been getting worse over the course of many years.

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