Brian Cashman has made a reputation of signing and trading for players in reactionary fashion. Here are three targets to avoid, and their comps.
Stay Away From: Alex Bregman
Recent Comparison: Jacoby Ellsbury
In what was, arguably, the worst free agent signing in Yankees history, back during the 2013-2014 offseason, Brian Cashman brought Jacoby Ellsbury from the Red Sox to the Big Apple. As we tend to remember now, the Ellsbury signing was a reactionary move from Cashman after Robinson Cano left the Yankees for the Seattle Mariners. However, the Yankees signed a contract with their new center fielder 5 days before (on December 7th) their second baseman left to move across the country (on December 12th). The writing must've been on the wall about Cano's soon-to-be-departure, and the Yankees ended up worse for it.
I fear that bringing in Alex Bregman would lead to a similar fate. This isn't to say Alex Bregman is the same type of player that Jacoby Ellsbury was. In fact, they are almost completely different. Ellsbury had already shown a concerning injury history and his game was held up almost entirely in his speed. He also had just one great season before he became a Yankee. Bregman, on the other hand, has stayed mostly healthy in his career and has relied more on hitting for power. He has also been very consistent as a hitter and defender.
My worry isn't that Bregman won't produce or that he'll miss a ton of games. My worry is that Bregman's contract will immediately be an obvious overpay and it will hold the Yankees back financially. It's been rumored that he is looking for at least a $200 Million contract, likely over 6 (a $33.3M AAV) or 7 (a $28.6M AAV) years. That's a lot of money and term for a hitter who's about to be 31 years old, whose best years were 2018 (+7.9 bWAR, 152 OPS+) and 2019 (+8.9 bWAR, 162 OPS+), and who hasn't topped 5 bWAR or a 135 OPS+ in the 5 seasons since then.
I think Bregman will still be a decently productive player, likely for the next 4-5 years. His defense is very good, and his bat will stay in a tier above average. However, just look at how fast that skillset can drop. Nolan Arenado had a +7.7 bWAR season as a glove-first, 31 year-old third baseman. In his age-32 and age-33 seasons, he hasn't topped a +2.5 bWAR. (And Arenado's bat was much better and consistent than Bregman's during his prime.)
Stay Away From: Nolan Arenado
Recent Comparison: Josh Donaldson
Speaking of Nolan Arenado, he's another player who has had rumors aligning him with the New York Yankees. And for him, I see another version of Josh Donaldson.
Josh Donaldson was 36-years-old when he came to the Yankees in a trade with Isiah Kiner-Falefa for Gary Sanchez and Gio Urshela. And, the basic idea of the trade did show promise at the time. Donaldson was coming off seasons with better than a 125 OPS+ in both 2019 and 2021 (and a 132 OPS+ in a shortened 2020), he still had a positive glove for third base, and he had that former MVP pedigree. And the Yankees took a huge gamble by taking on his remaining contract of 2/$50M with a $6M option for a 3rd year.
Nolan Arenado will be 34-years-old next season, and I could very easily see him be traded for a package that includes Jose Trevino. However, Arenado is coming off back-to-back 108 and 101 OPS+ seasons in 2023 and 2024 and he has no MVP pedigree (though he's come close a few times). His glove is his best asset, but Arenado has also said he'd be willing to move to first base, which would tank whatever positive value he'd have left. He also comes with a serious contract of 3/$74M remaining.
Luckily, as I'm writing this piece, Jack Curry has come out in stating that Nolan Arenado is well respected by the Yankees, but he's not seen as a fit. Additionally (in the same video clip from that linked tweet), Curry has also mentioned that members of the Yankees don't believe Alex Bregman's swing fits Yankee Stadium and he doesn't see much interest in his services.
Stay Away From: Pete Alonso
Recent Comparison: Gary Sheffield
I like Pete Alonso. Not as target for the Yankees, but as a ballplayer. From what I see and read, he seems like a good guy and I wish him all the best in his free agency. (And, I ultimately see him re-signing with the New York Mets.)
However, in the wake of Juan Soto skipping town from the Bronx to Flushing, this would be an absolutely embarrassing move for the Yankees to make. It would be a token move to solidify that the New York Yankees are the "little brother" to the New York Mets. It would be a counter-move solely to take a player from the Mets, who doesn't really fit the needs of the Yankees, just to make a statement. And, that statement would not bother the Mets at all.
Take it from me. I'm the younger brother, twice over. When my older brothers would take something from me that I wanted, I'd try and take something from them as revenge. They never cared and it never bothered them, and that only made it worse.
The Yankees, historically, have not lost a lot of big time free agents. However, they did lose out on Vladimir Guerrero, instead opting to sign Gary Sheffield. (Again, this gets mis-remembered by Yankees fans, as Sheffield had signed in December of 2003, while Guerrero didn't sign until January of 2004, but I digress.) And, I don't think it's a stretch to say that Vladimir Guerrero was ultimately the better move.
However, this isn't to say that Pete Alonso could never be on the table for the Yankees. Let's pretend it's late January/early February, Pete Alonso still isn't signed anywhere, and the Yankees have Cody Bellinger, who they could easily move to center field. Then, it's not a bad move to make to take him on a short-term contract. The problem with signing Alonso would be the proximity in time to the Juan Soto signing. Right now? Absolutely not. In a month or so? It could be a smart short-term move.