New York Yankees to Re-Enter Jordan Montgomery Talks? Pitching Search Continues Amidst Blake Snell Buzz

It isn’t every year when the free agent market is filled with stars, even after the start of Spring Training. However, if one knows anything about Scott Boras, it isn’t surprising that he has extended his clients’ free agency to such an extent. Interestingly, two of his top clients, Blake Snell and Jordan Montgomery, have been linked with the New York Yankees at different points this season. Now, with things expected to pick up their pace soon, is there a chance that the Pinstripes will end up with either of them?

The situations cannot be much different than what they are right now. On one hand, Blake Snell has already expressed his interest in the Bronx Bombers. But on the other hand, Montgomery has a deep history with the team. In most cases, history could lead to a reunion, but something has stopped this connection. 

New York Yankees, the favorites for Scott Boras’ golden clients

Ever since the offseason began, the world has watched Blake Snell and Jordan Montgomery with baited eyes. Both stars were coming off their career high points – second Cy Young for Snell and World Series for Montgomery. One common thread in their free agencies was the apparent links with the Yankees. However, the memories of Monty’s trade are still fresh.

While it is true that Montgomery has been a Yankee for the majority of his career. More importantly, he was one of the most beloved parts of the roster. But his abrupt exit from the Pinstripes left a sour taste in many mouths. The Bombers traded him when they were on a high. At that time, Monty was expendable, but things have changed since then.

Instead of growing, the Yankees declined in 2023. Simultaneously, Monty’s career blossomed, and he went on to play a crucial role in the Texas Rangers’ maiden World Series win. While the pitcher has declined to have any ill will for the Bombers, one couldn’t ignore the speculations.

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Still, as Andy Martino of SNY said, “As long as Snell and Montgomery remain on the open market, they can’t be totally ruled out for the Yankees.” But one thing can affect this connection – it’s not history but the future. 

The cost of Jordan Montgomery and the limits of the Bombers 

Multiple reports had emerged recently that the Philadelphia Phillies were interested in Montgomery, but they preferred a short-term deal. Monty didn’t agree with this demand, especially after he’s had his career-best season. This could be an important lesson for the Yankees as well.

With a payroll that has crossed $300 million, the Bronx squad doesn’t have a lot of wiggle room. More importantly, their expected pursuit of Juan Soto next year makes being a little frugal this season an obvious choice. It’s one of the reasons why, despite a clear interest, they’ve not gone all out for Snell.

So as of now, it’s just a giant wait-and-watch situation.

Read more: 12 Top Free Agents Still on the Market – Does Rob Manfred’s Deadline Proposal Hold Water?