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Will The Yankees Regret Trading Away Jordan Montgomery?

Jordan Montgomery
Will the Yankees regret trading away Jordan Montgomery? Montgomery oddly enough makes his first start for the Cardinals against New York. (Joe Puetz | Getty Images)

Will The Yankees Regret Trading Away Jordan Montgomery?

Aggressive wins but Brian Cashman is certainly playing with fire. Finding capable starting pitching is hard. Giving that away for medium upside gambles is playing a very dangerous game. In a vacuum, trading away Jordan Montgomery for Harrison Bader left a lot of Yankee fans scratching their heads. In reality, I’m about as torn on this trade as it gets.

The Chinese farmer always says maybe and if you gave Cashman a little bit of truth serum, he’s likely sweating bullets. Montgomery is set to make his first start with the Cardinals today against his former club in what will likely be an awkward moment for the left-handed starter. If that’s not a sign of things to come, then I’m not seeing the board and we all know that’s not true.

“It’s awkward,’’ Montgomery said in St. Louis before the Yankees’ 4-3 series-opening loss to the Cardinals on Friday. “It’s strange timing, but it’s a business and I’ll treat it like any other game. … I didn’t want to face them the first time I’m pitching for a new organization, but I’m a competitor and will shake off the nerves.” 

“I used to think I’d be a Yankee for life,” Montgomery said. 

“If [Cashman] thinks that, I don’t care,’’ Montgomery said. “I’m excited to be wanted. I’m a Cardinal now. I’ll give it my best.” 

Did you hear that? Did that send a shiver down every Yankee fan’s spine? Words are just words but this sounds like a guy ready to prove his former boss wrong. Nobody is saying Jordan Montgomery is the savior for the Cardinals but he can pitch. Make no mistake about it.

Montgomery, 29, has a unique skill set but he’s someone you have no quarrels with being your 4th or 5th starter on a really good team. The fastball sits at about 92-93 MPH. It’s a four-pitch mix that includes a changeup, curveball, and cutter. Montgomery controls the strike zone and his 6-foot-6 frame helps make his pitches have that little extra life on them to throw hitters off.

More importantly, this guy gets through innings. In 2022, Montgomery currently sports a 3.69 ERA in 21 starts. The pure stuff isn’t elite but he knows his spots and makes hitters expand the zone. The new Cardinals starter ranks in the 90th percentile in chase rate and 77th percentile in whiff rate. The way he’s able to work the cutter often makes the fastball play differently.

Montgomery also doesn’t beat himself. He ranks in the 92nd percentile in walk rate. Left-handed starters that can eat innings, make hitters chase outside of the zone, and that can control the strike zone are incredibly valuable. That’s exactly what Montgomery is.

As I sit here today, I also see the other side of it. Montgomery’s stock is high right now. With just one more year of team control to go, maybe New York felt it was either do this now or be faced with knowing they won’t match his next contract elsewhere at the end of 2023 when he will start to age into his 30s. To move Montgomery for a player like Harrison Bader that has his defensive acumen in centerfield has some credence to it.

Let’s not get it twisted, Bader is an upgrade over Aaron Hicks. New York also didn’t have another centerfield option in the farm system. Estevan Florial isn’t that guy. Furthermore, New York knows they can’t rely on Aaron Judge to save them forever. The less wear and tear on his body the better. It just makes way more sense to have Judge in right field.

The only problem is Bader isn’t healthy. Oh, I meant like ever. He’s never healthy. Bader is currently in a walking boot and we really have no idea if he’s even going to play this year. Bader has missed a significant portion of each of the last three years. Is that really the type of gamble that’s worth giving away Montgomery for?

It feels like the Yankees never have enough pitching. Montgomery was at least reliable to take the ball every 5th day and put together a respectable start. There is something to be said for that. There is a rollercoaster element that remains intact with virtually every starter in the Yankees rotation. In a postseason series where you need quality starts, how many of these guys do you actually trust?

As I said, I don’t hate the gamble for Bader. He’s a former gold glover for a reason. Defense matters and this guy is going to save a lot of potential hits. The bat sort of plays but doesn’t come with much power or on-base ability. You can easily see the pathway of him becoming the younger version of Aaron Hicks that Yankee fans wish still existed. Bader is also cheaper than Montgomery with the same amount of team control. He will cost less via arbitration next year too.

Nevertheless, it’s still a wacky deal. There was no reason to trade Montgomery. Especially given the Yankees’ path towards postseason play. It makes even less sense to trade a guy who is reliable for someone that isn’t. This trade could have the ultimate butterfly effect. Something that could have made or broke New York’s chances this year. All I know is somewhere in the Yankees front office, Cashman has to be nervous regardless of how this one plays out.

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