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Why the Jordan Montgomery Trade Was a Risk For the Yankees

New York's decision to part ways with Jordan Montgomery makes sense, but it's also a significant risk for this club's pitching staff leading up to October.
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Jordan Montgomery was always going to pitch during this weekend's series between the Yankees and Cardinals in St. Louis.

It followed his five-day routine in New York's pitching staff after his latest outing on Sunday against the Royals.

Rather than taking the mound in his road grays, the uniform he's worn in ballparks away from the Bronx for his entire career, Montgomery will take the field in Cardinal red on Saturday, making his debut for his new squad.

New York traded Montgomery to St. Louis minutes before the trade deadline on Tuesday, a head-scratching deal that came out of nowhere, sending injured outfielder Harrison Bader back to the Yankees.

While perplexing and shocking on the surface, it's easier to rationalize the Montgomery trade through a lens that's focused on October. 

Odds are, the lanky lefty wouldn't have factored in to New York's postseason rotation. The Yankees are currently poised to hand the ball to Gerrit Cole, Frankie Montas (who was acquired before the deadline from Oakland), Nestor Cortes and a healthy Luis Severino. 

Further, assuming Bader returns from his case of plantar fasciitis before the end of the season, New York is adding an impact player at a position of need. Center field has been the weakest position for the Yankees on defense this season. Bader is one of the best defensive center fielders in the game (plus-38 defensive runs saved in center in his career) and a constant threat to steal on the bases, bringing superior attributes to the table than Aaron Hicks (who has descended into another brutal slump offensively). 

Nonetheless, this deal also comes with trepidation. 

Here are a few reasons why the Montgomery trade was a risk for New York, a move that general manager Brian Cashman may regret over the next few months and beyond. 

Depth in the Starting Rotation

Montgomery wasn't the only starting pitcher the Yankees traded away ahead of this year's deadline.

New York included left-handers JP Sears and Ken Waldichuk in the Montas deal, acquiring reliever Scott Effross from the Cubs in exchange for righty Hayden Wesneski. Each of those three hurlers were in the rotation in Triple-A Scranton/Wilkes-Barre. While Sears had already pitched seven times with the Yankees this year, Waldichuk and Wesneski were top-10 prospects knocking on the door of a promotion, ready to step in if needed.

With Luis Gil out for the year after Tommy John surgery, that leaves Clarke Schmidt and Ryan Weber as the only other pitchers in Triple-A with big-league experience as a starter. 

Weber, 31, has been an emergency reliever in pinstripes a few times this year, posting a 1.17 ERA in three games. Deivi García, who was once New York's No. 2 pitching prospect, is also in the farm system, currently pitching for the Somerset Patriots in Double-A. He's had another tough year in the minors, though, posting a 7.85 ERA this season, recently returning from a two-month stint on the IL.

All of that in mind, the depth of starting pitching in the organization that's capable of making an impact at the big-league level took a significant hit this week. It's possible that Domingo Germán can hold it down in his current place in the starting staff while Montas settles into Montgomery's spot, pitching to his potential. Severino is on the mend and even if he can't return until September on the 60-day injured list, he's still poised to play a role down the stretch. Schmidt is biding his time for a starting opportunity as he builds up in Scranton/Wilkes-Barre, something he's earned over the last few years. 

If any additional adversity happens to hit the core members of New York's rotation—or if certain starters like Jameson Taillon continue to struggle—however, the Yankees will be in trouble.

New York has built enough of a cushion in their division where a dip in their winning ways is an easier pill to swallow. All they need to do is get to October with this current group, transitioning to a part of the year where fewer starters are needed. 

Montgomery wasn't flashy, but he typically gave his team a chance to win every time he toed the slab. Taking that away, when you can never have enough reliable pitching, is a risk.

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Postseason Pitching Staff

Even if Montgomery wasn't going to get a start in the playoffs, he still could've been on the roster as an option out of the bullpen. 

The left-hander hasn't pitched in relief many times in his professional career, even dating back to his days with the South Carolina Gamecocks, but all bets are off in the playoffs. Don't you think New York would've been able to find a spot for him on their postseason roster as insurance if one of their starters gets hurt or doesn't have his best stuff after an inning or two?

When you look at New York's current pitching staff, the only reliever to go more than two innings out of the bullpen this season is southpaw Lucas Luetge, a pitcher that might not factor into the equation in the postseason either. 

Germán could be used in that role, but the right-hander has a 6.39 ERA this season and a 4.60 ERA in his career with the Yankees. The same can be said for Taillon, who has a 5.73 ERA in his last 11 starts (since June 7). Those options don't seem like a first choice for New York entering the playoffs. Schmidt, meanwhile, would be making his postseason debut if called upon in October.

CC Sabathia and J.A. Happ came out of the bullpen for the Yankees during the 2019 postseason. As noted by Eno Sarris of The Athletic in his breakdown of the Montgomery trade, starters like Nathan Eovaldi, Julio Urias, Christian Javier and more also came out of the bullpen for their respective clubs in the postseason over the last few years.

This entire issue is in large part a consequence of Michael King being injured and out for the rest of the year. That loss for New York's bullpen hasn't been talked about as much since the team added arms at the deadline, but it's still a devastating blow, subtracting one of the best multi-inning relievers in baseball for the most important time of the year.

Manager Aaron Boone has options. Newly-acquired arms Effross and Lou Trivino (also from the Athletics) have fit in nicely so far while the likes of Aroldis Chapman and Jonathan Loáisiga are in the process of recapturing their old form. Zack Britton is working to return before the end of the regular season as well, a veteran to complement other pieces like Wandy Peralta, Ron Marinaccio and closer Clay Holmes. 

If New York wants to win a championship, however, their depth will be tested along that lengthy path to the World Series.

Harrison Bader's Health

Bader appears to be a tremendous fit for this club, set to contribute with elite defense and speed. He's got some sneaky pop at the plate as well.

Whether he's used as a starter playing over Hicks or as a reserve off the bench—a better fourth outfielder than Tim Locastro—Bader will absolutely have an impact and bring a spark to October.

But Bader is currently in a walking boot. He's confident he'll be back before the end of the regular season from his plantar fasciitis, but he's at least a month away from his first in-game action with the Yankees, possibly more.

Cashman shared in that same optimism, assuring that New York did a deep dive on Bader's medicals before pulling the trigger on this trade. A foot injury for a player that excels while tracking down balls in the gap or stealing bases is certainly a cause for concern, though. 

What if Bader has a setback? Will he be able to assimilate with his new club and get enough playing time before the postseason begins in order to be at his best? As we've seen in the past with players like Luke Voit, plantar fasciitis can have a lasting impact on assets between the lines. 

Before going on the injured list, Bader was having the worst defensive season of his career in terms of defensive runs saved (minus-two, per FanGraphs after producing plus-15 in each of his two previous full seasons). 

There's no denying Bader is a quality fit and can help this club (in 2023 as well), playing for the team he grew up rooting for. That doesn't erase the risk attached to his status for the playoffs. 

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