Why the Phillies should pursue Jordan Montgomery on a short-term deal

If you’re looking for the Phillies to make one last big splash in free agency, the chances of that happening increased over the weekend.

Cody Bellinger reportedly agreed to re-sign with the Chicago Cubs on a three-year, $80 million deal early Sunday morning. The deals pays Bellinger $30 million in each of the first two years and $20 million in the last and includes opt outs after the first two years.

Is it a bad deal for Bellinger? Maybe. The 29-year-old has two years to parlay another good year into another big contract. Handing over $150 to $200 million for a player who was non-tendered after 2022 was always going to be a tough sell. He’s going to need another year to prove to teams that he’s still a top position player in the sport.

This is all relevant to the Phillies because the Bellinger deal could be the beginning of the end of a months-long stare down between Boras and teams interested in his top clients.

Three years, $80 million is not the deal Boras wanted for Bellinger. It’s unclear how much Boras was actually seeking, but Bob Nightengale of USA Today put out a number as high as $250 million back in December.

If Bellinger’s deal is indicative of what’s to come for Matt Chapman, Blake Snell and Jordan Montgomery, Boras’ best remaining clients available on the market, this offseason will not be remembered as one of Boras’ finest.

And that could lead to an opening for the Phillies, who have shown interest in Montgomery on a short-term deal, according to MLB.com’s Todd Zolecki.

The Phillies already have one of the best rotations in baseball, with Zack Wheeler, Aaron Nola, Ranger Suárez, Taijuan Walker and Cristopher Sánchez locked in for this year. They also handed out major league deals to starters Kolby Allard and Spencer Turnbull. Turnbull could start the year in the bullpen as a long man, but both function as depth in the event a starter goes down. Nick Nelson, Dylan Covey and non-roster invitee David Buchanan are also being stretched out.

The Phillies technically do not need to add to the rotation, but there is room for Montgomery.

The team wants to win its first NL East title since 2011, but in all likelihood, the Phillies are going to have to get through another tricky three-game playoff series to get a chance to upset the Braves or Dodgers in the NLDS. The Phillies have taken care of business each of the last two years with Wheeler and Nola on the mound against St. Louis and Miami, but what if an injury pops up and the Phillies’ winning formula is compromised? Suárez can step up, but what happens if there is a Game 3?

Montgomery would be a heck of an insurance policy and then some. He’s not as talented as Wheeler, but the two have followed a remarkably similar path. Both began their careers in New York, came back strong after Tommy John surgery and saw their careers take off after leaving town. Wheeler cashed in and then became one of the five best starters in baseball with the Phillies. Montgomery is still looking for his big payday.

Montgomery has made at least 30 starts in each of the last three years and has a 3.48 ERA over that time frame. The Yankees didn’t think he was good enough to start a postseason game, so they traded him to the Cardinals for Harrison Bader at the 2022 trade deadline. St. Louis used Montgomery out of the bullpen against the Phillies in Game 2 of the 2022 NL Wild Card Series.

Montgomery’s stock rose dramatically when he was traded from the Cardinals to the Rangers at the deadline in 2023. He made 11 starts for Texas in the regular season and posted a 2.90 ERA. He began his first postseason run as a starter with seven shutout innings against the Rays in Game 1 of the Wild Card Series. After a clunker against the Orioles in the ALDS, Montgomery pitched 6 1/3 scoreless innings against the Astros in the ALCS and recorded seven outs out of the bullpen in the Game 7 clincher against Houston.

Montgomery was rumored to go back to the Rangers all offseason, but that hasn’t happened yet because of Texas’ television revenue situation. It’s been resolved for this year, but there’s uncertainty surrounding future years. The Rangers are the most likely team to jump in and re-sign Montgomery on a short-term deal, but in the event that doesn’t happen, the Phillies could swoop in.

The Red Sox are another rumored landing spot. Manager Alex Cora confirmed to reporters that the team met with Montgomery via Zoom two weeks ago. That usually doesn’t mean anything. Mark Feinsand of MLB.com thinks the Los Angeles Angels will likely end up with one of Montgomery or Snell.

All of the teams listed above are more desperate for starting pitching, but the Phillies are the most desperate out of the bunch to win a World Series this year.

Signing Montgomery would almost certainly push the Phillies’ payroll past the $277 million third luxury tax and lead to the Phillies’ first-round draft pick next year moving back ten spots. Considering the team’s final bid for Yoshinobu Yamamato reportedly exceeded $300 million, it’s safe to assume that the Phillies are comfortable taking their payroll to unprecedented heights for the right move.

With Wheeler, Nola, Bryce Harper, Trea Turner and others all under contract and in their prime, the team’s best chance to win the final game of the season is within the next two or three years.

Harper said it best last week in Clearwater.

“We gotta win more games and understand that this is a window that we’ve got to win in,” Harper said. “Ownership deserves that. [Dave] Dombrowski deserves that. Our fans deserve that as well, and we do too.”

Not many teams have four playoff-caliber starters in the rotation and a team like the Phillies should be opportunistic. It doesn’t cost anything to make an offer and that’s at the very least what the Phillies should do with Montgomery.

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