5 best free agents available after Shohei Ohtani deal and where they’ll sign

4. Jordan Montgomery will sign with the New York Yankees

The New York Yankees are still aggressive on the free agent front despite spending considerable assets to acquire Juan Soto via trade. The expectation is that New York will look to address pitching concerns, acquiring another high-level arm to pair with 2023 Cy Young winner Gerritt Cole.

Jordan Montgomery spent the first five years (and change) of his MLB career with the Yankees, before he was dealt to the St. Louis Cardinals in 2022 and subsequently dealt to the Texas Rangers last season. All signs point to Montgomery wanting to re-sign in Texas, where he experienced great success en route to a World Series victory.

That said, it would appear the Rangers are lacking on the financial front due to uncertainty about their local TV rights deal. If Texas gets priced out of the Montgomery sweepstakes, the Yankees are equipped with deep pockets and the ability to out-spend anybody. Montgomery could feel a certain way about New York's decision to trade him a couple of years ago, but the idea of winning in pinstripes on a major long-term contract tends to hold mass appeal across the MLB landscape.

Montgomery is the perfect No. 2 ace to slot behind Cole in the rotation. He got off to a rocky start with the Cardinals in 2023, largely for reasons outside his control. Once Montgomery arrived in Texas, however, he was electric. In six postseason appearances (five starts), Montgomery posted a 3-1 record with a 2.90 ERA and 3.90 FIP, allowing 37 hits and registering 17 strikeouts in 31.0 innings.