A ‘dream come true’ for one could be a ‘heartbreak for another’. More importantly, it’s interesting how two stories can make parallels, leading to different ends. Luis Gil and Jordan Montgomery are similar in two ways – they debuted with the New York Yankees and are beloved by the fans. As a result, Monty’s return is not only anticipated but encouraged. But in a cruel twist of fate, it could be that other Yankees’ homeboy whose return prevents Monty’s re-entry to The Bronx.

Ever since Gerrit Cole’s unfortunate injury, the Pinstripes have been scrambling for a No.5. Certainly, Montgomery could’ve been a great option if they could move past the wounds of his 2022 trade. And the talks did suggest the two sides were ready to pursue a common avenue. But then the news broke – Luis Gil is now the no.5 starter of the Yankees, with that burst the balloon on the Monty connection. But is it really the end?

Luis Gil’s dream job disappoints the Jordan Montgomery reunion stans

Luis Gil’s appointment isn’t that surprising. After all, the firebreathing pitcher has been on a roll since the start of this Spring Training. In 15 ⅔ innings pitched, he has a 2.87 ERA and has given just 5 runs. Impressively, Gil has struck out a team-leading 23 hitters. That strike-out number is key because the Yankees have always favored that over flyballs. However, that has led to questions getting raised over Montgomery’s links. 

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Famous insider Jim Bowden reported on Sunday that Montgomery’s market had arrived. He highlighted that the World Series pitcher has two long-term contract offers with him. Fans quickly named the Yankees and the Boston Red Sox as possible suitors. After all, they were the only ones left whose lineups weren’t looking impressive.

But then that 110% tax issue of the Bombers was always a big hindrance on this deal. Even a salary of $20 million would’ve cost the Yankees over $40 million. And now the appointment of Gil has just made those doubts far more audible. On top of that Aaron Boone said (via MLB.com) that based on past performances the 25-year-old has “certainly earned” a starting position.

With the season opener just two days away and with Montgomery’s links with the New York Yankees weakening, what is the pitcher waiting for? Could the speculation regarding a qualifying offer be true?

Is an urge to avoid a qualifying offer delaying Monty’s signing?

The biggest advantage that Montgomery had was the fact that he was free of any qualifying offers. However, if the star signs a short-term deal (like other Scott Boras clients) he’d risk getting one next season. But if the World Series winner enters the season without any deal he’d be disqualified from getting a qualifying offer next season. Could this delay be a way for Monty to avoid that offer?

Rejecting a qualifying offer puts penalties on any team signing you. With draft picks becoming increasingly important for teams those penalties aren’t desirable. With the clock ticking rapidly, the speculations are becoming more credible. Just when will Montgomery’s nightmarish free agency end? Soon enough we’ll find out.

How Does the Yankees Rotation Look with Luis Gil?