If Phillies make another big free agent pitching splash, Jordan Montgomery is the best fit
The Phillies are not expected to make another big splash in free agency. Three talented lefties, starters Blake Snell, Jordan Montgomery and reliever Josh Hader, are the biggest prizes left on the pitching market. Multiple insiders have connected the Phillies to all three pitchers, but those connections are likely rooted in the team’s prior interest in signing Yoshinobu Yamamoto.
At the same time, nothing can be ruled out. During the 2021-22 offseason, the Phillies were expected to sign one of the top free agent outfielders on the market. They were connected to Kyle Schwarber prior to the lockout and signed him to a four-year, $79 million contract shortly after the end of the work stoppage. When Nick Castellanos’ market did not develop as anticipated, Dave Dombrowski went to ownership and was given the green light to take the team over the luxury tax and sign Castellanos to a $100 million deal.
If the Phillies want to make another splash, Montgomery would be the best fit out of the three big lefties available.
Montgomery, 31, is in line for a big payday following an excellent 2023 season with the St. Louis Cardinals and Texas Rangers. He pitched to a 3.20 ERA across 188 2/3 innings during the regular season. He was traded from the Cardinals to the Rangers at the deadline, where he thrived down the stretch. Montgomery posted a 2.79 ERA in 11 regular season starts with Texas. He threw at least 6 1/3 scoreless innings in two of his first three playoff starts and threw 2 1/3 scoreless innings out of the bullpen in a Game 7 win in the ALCS against the Astros.
He got hit hard in his ALDS start against the Orioles and in Game 2 of the World Series against the D-Backs, but he proved he has what it takes to pitch in October.
He’ll parlay that stretch with the Rangers into a big contract. Montgomery, who is a Scott Boras client, will almost certainly land a deal worth over $100 million. It’s just a matter of who will sign him and how close does he get to Aaron Nola’s $172 million guarantee.
One thing Montgomery has working for him is, unlike Snell and Hader, he does not have a qualifying offer attached to him. If the Phillies wanted to sign either Snell or Hader, that would require the team to give up their second- and fifth-highest selections in next year’s draft along with one million in international bonus pool money. Losing picks impacts an entire draft as teams also lose the bonus money allocated to those picks. For a team like the Phillies, who want to build up their farm system, it’s a price they should not pay. Montgomery was not eligible to receive the qualifying offer because he was traded during the season.
Without the presence of the qualifying offer, Hader seems like the perfect fit on the surface level. Now that Craig Kimbrel is gone, the Phillies could use a top closer. Some have argued that the Phillies would have won the NLCS if they had Hader instead of Kimbrel, but that line of thinking ignores a few things. Hader would have pitched the ninth inning of Game 3, but the Phillies still would have had to score in extras to win and survive with Seranthony Domínguez and Matt Strahm being the two viable bullpen options remaining. The lineup scored only one run in Game 3 on a wild pitch.
It’s also possible Hader would have entered Game 4 in the eighth in Kimbrel’s spot and pitched a clean inning, but the Phillies would have had to navigate the top of the D-Backs order with a tired José Alvarado or Michael Lorenzen in the ninth because Hader is almost exclusively a three-out pitcher. He wasn’t going to come back out for the ninth inning in a contract year and with the state of the Phillies bullpen at the time, there was no guarantee that they were going to get through the bottom of the ninth inning with the lead.
Signing Hader, regardless of the acquisition cost, could be tempting. But over the past few seasons, the Phillies have had a decent track record of unearthing under-the-radar arms and turning them into really good back end relievers, with Alvarado and Jeff Hoffman being the best examples. And if they are high on Orion Kerkering, it might not be wise to spend that much money on one reliever.
The Phillies have depth concerns in the rotation. The top five of Nola, Zack Wheeler, Ranger Suárez, Taijuan Walker and Cristopher Sanchez is one of the best in baseball, but the depth behind them is bleak. Signing another big starter like Snell or Montgomery gives the Phillies four playoff-tested starters and shifts Sánchez to a swingman role.
But Montgomery, not Snell, is the better fit for Philadelphia because the Phillies like having dependable starters at the top. Outside of his two Cy Young Award seasons in 2018 and 2023, Snell has not thrown more than 130 innings in a season. Handing over $200 million to someone who cannot be relied on for 180-200 innings doesn’t seem like something the Phillies would do.
Montgomery might not have as high of a ceiling as Snell, but he brings a mix of dependability in the regular season and postseason success that could intrigue the Phillies.
The Phillies have been lucky to have Wheeler, Nola and Suárez healthy for both playoff runs. There’s no guarantee that all three will remain healthy come October for a third year in a row, so it might be smart to mimic Texas’ strategy of stocking up on big name starting pitchers.
The Rangers, however, seem like the likeliest landing spot for Montgomery. Bob Nightengale of USA Today reported on Sunday that Montgomery prefers to go back to Texas. The only thing that can prevent the Rangers from re-signing Montgomery is the uncertainty surrounding the team’s television deal with Diamond Sports Group for 2024 and beyond. A lack of a timely resolution could lead to Montgomery signing elsewhere.
For the Phillies, a second pricey free agent pitching acquisition seems unlikely, but there is no harm in continuing to monitor the market.
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