Jordan Montgomery Free Agency Update: Yankees not 'confident' of reunion with World Series winner after missing out on Blake Snell

One would imagine the likeliness of the New York Yankees pivoting towards Jordan Montgomery as a likely target after missing out on Blake Snell. But according to MLB analyst Jon Heyman, the Yankees organization feels that the World Series champion might not be looking to make a comeback in the Bronx before Opening Day:

"The Yankees will continue to pursue starting pitching but their options are limited, particularly since they are even less confident Jordan Montgomery, the top remaining free agent, is interested in returning to The Bronx." - Jon Heyman via New York Post

Blake Snell completed a sensational move to the San Francisco Giants on Monday, and now that just leaves Jordan Montgomery as the No. 1 starting pitcher in free agency. Rumors have it that the Texas Rangers are trying to lure their star southpaw back to Globe Life Field while the Boston Red Sox and Chicago Cubs too remain in the fray.

Heyman had earlier reported that Montgomery is aspiring for a seven-year deal, which not many ballclubs are favoring to offer at this point, now just days away from the new season. The Yankees might be willing to offer the same, but they are very close to going overboard with their luxury tax in 2024.

The Red Sox have been mainly apprehensive because of Montgomery wanting a long-term deal, while the Cubs – having signed Shota Imanga previously – are in no hurry to extend any offers to Montgomery at the moment. Notably, both ballclubs are looking for more pitching depth in their bullpen.

Blake Snell was in a similar situation, demanding a hefty deal in free agency, and his NL Cy Young Award was making a case for it, but due to a lack of contractual discussions and the rescinding interests of the ballclubs, he had to settle for a two-year, $62 million deal with the Giants, which involves an opt-out clause after the first year.

Should Jordan Montgomery follow in the footsteps of Blake Snell and sign a shorter deal?

Baseball analysts will likely agree that Jordan Montgomery should look to sign a shorter deal, along the lines of what Blake Snell did with the Giants. The catch is that both of these ace strike throwers are 31 years old and still have some gas left in their tanks.

Like Snell, Montgomery would benefit from a deal that gives him a decent amount of salary over those years while stipulating an opt-out clause to always find better suitors in the market later on among the various MLB giants.

Blake Snell would be 33 years old by the time his contract ends with San Francisco, which would give him a lot more options to exercise later in his career, and Montgomery can look to do the same in the coming days before the start of the 2024 MLB season.