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The New York Yankees rarely miss what they covet, but Yoshinobu Yamamoto was a surprising failure. The Japanese ace all of MLB was going after in a rare instance of madness ended up signing a record-breaking deal with the Los Angeles Dodgers. The teams he spurned were left high and dry, forced to fall back on a Plan B. But the Bronx is caught in an interesting dilemma between Jordan Montgomery and Shota Imanaga.

The Yankees’ biggest problem in 2023 was offense, but while Cy Young winner Gerrit Cole led the charge for the bullpen, it was starkly lacking in star power. With much of the team’s pitching depth now having gone to the Padres for Juan Soto, the Yankees must regroup. Even if the club has the confounding ability to bring up talented relievers out of thin air, the starting rotation could use some help. Will they use an MLB veteran or a relative rookie?

The Throwing Philosopher vs. Gumby – New York Yankees In a Deep Fix

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Amidst accusations of not being committed enough to offer Yoshinobu Yamamoto a deal that could surpass Gerrit Cole’s, the New York Yankees must face the music now. Some insiders suggested that even if the Japanese ace had come to the Bronx, the club would not have stopped with him in the bullpen. Perhaps Jordan Montgomery and Shota Imanaga had always been in their sights. But whether or not to go after the Japanese or the former Pinstriper is the question.

Per Sports Illustrated, Imanaga, though not quite the same as Yamamoto, “struck out nearly 30 percent of the hitters he faced. He walked just 3.8 percent of the hitters he faced, too.” Not to mention his relatively low market value – analysts predict a $100 million contract for five years at most. A dream signing?

Could be, if the Yankees ignore his inexperience in MLB. The Japanese league is rated somewhere between MLB’s Triple-A and majors level, so signing ‘The Throwing Philosopher’ poses concerns. Jordan Montgomery, on the other hand, is a seasoned veteran of the game with a World Series title to boast now. But while New York may be waiting with open hands to welcome him back, will Gumby even accept them?

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WATCH THIS STORY – Mets Gear Up For Yamamoto Showdown: Going All In Amidst Intense Yankees Pursuit

The Yankees Will Have to Go Above and Beyond for Jordan Montgomery

When the Yankees traded away Jordan Montgomery to St. Louis last year, no party involved would have thought the pitcher would be boasting a World Series title that he rightfully won in 2023. With the Texas Rangers no less, a team that hadn’t won a trophy in years of their existence. But it happened, and now Monty is a free agent, ready to bestow his talents elsewhere.

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While Ken Rosenthal of The Athletic reports there are internal conversations about bringing him back to the Bronx, some believe it would take much more than the Yankees may be willing to give Montgomery. With increased value, and the 2022 trade to hold against them, will Jordan Montgomery choose to wear Pinstripes again?

READ MORE – Despite Yankees’ Imanaga and Montgomery Connections, Corbin Burnes May Emerge in Talks After Missing Yoshinobu Yamamoto