Jordan Montgomery free agency odds seek Yankees reunion

With the Yankees looking to make up for their missed playoff opportunity, New York could re-unite with Jordan Montgomery.

For the first time since 2016, the New York Yankees missed out on the playoffs. While they have Gerrit Cole atop their rotation, the Yankees are still looking to add some firepower to their pitching staff.

New York is the favorite to sign Jordan Montgomery (+200), via betonline.ag. The St. Louis Cardinals (+300) and Boston Red Sox (+500) round out the top tree while the Milwaukee Brewers (+700) and Los Angeles Dodgers (+900) make up the top five.

Montgomery was drafted by the Yankees in the fourth round of the 2014 MLB Draft. He appeared in 98 games over his six years in New York, pitching to a 22-20 record with a 3.94 ERA and a 705/207 K/BB ratio. He was ultimately dealt to the St. Louis Cardinals for Harrison Bader in 2022.

However, that wouldn't be the last time Montgomery was on the move. The Cardinals traded the left-hander to the Texas Rangers midway through the 2023 season. Upon arrival, Montgomery pitched to a 4-2 record with a 2.79 ERA and a 58/13 K/BB ratio over his 11 starts. With Montgomery on their roster, the Rangers took down the Arizona Diamondbacks for their first World Series title.

Between his overall work and Texas and now championship acumen, Jordan Montgomery has now become one of the hottest pitchers on the free agent market. While there has been no word on if New York has initiated contact, Vegas at least believes there's a strong chance Montgomery winds up in pinstripes. The Yankees traded Montgomery away and saw him win a World Series. Their only wish is that when/if he wins another, it comes in New York.