3 Yankees trade regrets that will sting even more in 2023

The 2022 New York Yankees looked a gift horse in the mouth at the MLB trade deadline, then traded that gift horse for a solid starting pitcher with terrible road splits.

If it felt like Brian Cashman’s bizarre sales spree, which featured most of the franchise’s upper-level pitching being cleared out and replaced by injured outfielders, took an ice pick to the season, that feeling was likely justified! According to Andy Martino, some players in the locker room sensed the Yankees taking the foot off the gas pedal on purpose after missing out on Luis Castillo. Fun for us!

That top-level pitching clear out means one thing: this deadline non-spree could look even worse in 2023.

After all, say what you will about the Yankees, but they’re still in a division race and playoff contention. Most of the arms they traded away (well, minus one) are currently getting their sea legs on non-contenders, well out of the spotlight. They’re taking advantage of the opportunities presented to them while looking electric, something they’d be doing in Scranton if they were still Yankee property.

But next year? The training wheels will be off, and the Yankees will be looking to replace Jameson Taillon and, OK, let’s be honest with ourselves, Luis Severino in the rotation. Could they pay Carlos Rodón and change the narrative again? Sure! Alongside Aaron Judge? Welp!

These three trade regrets will linger into 2023 in a major way — and honorable mention to the Gio Urshela trade. There’s another year of Josh Donaldson on the horizon?! Could’ve just DFA’d Gary Sánchez and gotten it over with.

3 Yankees trade regrets that will sink 2023 season

3. Jordan Montgomery

Alrighty, well … the Jordan Montgomery St. Louis bounce back doesn’t look like much of a fluke anymore, now does it?

Montgomery might not be this good into 2023 and beyond (1.45 ERAs are hard to come by), but the left-hander has made tangible changes after being fluffed up by St. Louis coaches, and now feels confident enough in his fastball to let it lead him into attack mode. Stuff doesn’t change in two weeks. This is all about being coached up, making it clear that Matt Blake might’ve … missed something?

Either way, it sure looks like Montgomery’s going to be part of a postseason rotation now, huh? So much for that trade justification!

The Yankees probably would’ve preferred this plussed-up version of Montgomery making starts over Clarke Schmidt these past few weeks as their division lead dwindled, and if they could add a free agent starter to the 2023 rotation right now, a theoretical Monty addition would rank just below the Verlander-deGrom-Rodón triumvirate.

All in all, a pretty big oopsie, considering the left-hander has made an obvious adjustment that the Yankees couldn’t facilitate to unlock his total package.

2. Ken Waldichuk (and Maybe JP Sears?)

Hey, at least they’re not on a real contender! That sure would be embarrassing!

What’s that? Oakland reloads and rebuilds on a shoestring budget every two years or so? They probably will be soon? Got it. Ah, well.

So far, so good for Ken Waldichuk in two starts at the big-league level. He looks like an intriguing variation of a back-end starter. Throughout his minor-league tenure, Waldichuk has typically gassed it up and created a lot of traffic on the bases, but pumped his way out of danger with a funky combination of high-velocity fastballs and bizarre breakers.

During his two MLB starts in Oakland, the left-hander has exerted himself for 4.2 high-stress innings against Washington and 5.1 three-run innings against the Braves, but has only allowed four total earned runs, striking out eight. You might not be able to pencil in Waldichuk to a playoff rotation in 2023, but he’d be an electric innings-eater for at least 100 frames with the Yankees (and perhaps even a good piggyback option for Nestor Cortes if he need some scaling back).

JP Sears, also dealt to Oakland, is the less volatile option (in theory; he’s coming off a six-run blowup against the Chicago White Sox). It’s difficult to say the Yankees are really going to miss Sears tremendously in 2023, considering the championship version of this Yankee team would not include the left-hander in a playoff rotation. But innings must be eaten, and he’s done almost nothing but succeed since getting the big-league call in the Bronx.

Frankie Montas, you’d better be as good as two people next year!