A modest proposal for the Orioles to sign free agent lefty Jordan Montgomery

With teams that slow played the free agent market this offseason swooping in to sign the remaining big names off the market on shorter term deals, like Cody Bellinger to the Chicago Cubs, and Matt Chapman and Blake Snell to the San Francisco Giants, one postseason hero remains unsigned.

With news that the Texas Rangers have signed starter Michael Lorenzen, it sounds as through they’ve pivoted away from re-signing postseason hero Jordan Montgomery, who went 3-1 with a 2.90 ERA in six appearances, including five starts, over 31 innings in the playoffs last fall.

With Jon Heyman of the New York Post reporting that the New York Yankees are “back in contact” with Montgomery’s agent, Scott Boras, following the Gerrit Cole sore elbow news, we may be getting closer to him signing with a team ahead of Opening Day next week.

Note Heyman adds there is still a gap between the 31-year-old southpaw’s asking price and New York’s comfort level in reacquiring him, as we’ve already seen with the Yankees pulling their six-year, $150 million offer for Blake Snell before he signed a two-year, $62 million deal with the Giants.

MLB Trade Rumors had predicted a six-year, $150 million free agent contract for Montgomery last November, and yet here we are, with him still available this close to the start of the 2024 season. At an AAV of $25 million, Montgomery’s effective cost on a Yankee deal would be $52.5 million for 2024, including the additional luxury tax penalty they would incur as a 110%, fourth-tier tax payor above the highest $297 million competitive balance tax (CBT) threshold. The Yankees have a current projected luxury tax payroll near $308 million.

Could the Orioles sweep in and nab Jordan Montgomery?

If Baltimore were to structure a similar higher value, two-year deal with an opt out for Montgomery at an AAV of $25-30 million, they wouldn’t incur any luxury tax penalty at a current projected luxury tax payroll of just over $122 million. With the Kyle Bradish injury, the Dylan Cease trade to San Diego, and the likelihood that ace Corbin Burnes plans to test free agency after the upcoming season, could Montgomery be a short term bridge for a few seasons at Camden Yards?

Would he be willing to accept a short-term pact like the rest of his Boras brethren, after holding out for long-term security all winter long? And as Darragh McDonald of MLBTR writes, “Perhaps it would be wise for him to look for the best short-term deal he can find but wait until after Opening Day to actually sign it.”

Baseball’s collective bargaining agreement states the qualifying offer (QO) applies to players like Montgomery who haven’t received a QO before, and who become free agents “after having been continuously under reserve (without interruption) to the same Club (either at the Major or Minor League level) since Opening Day of the recently completed championship season," which could be relevant if he has a great season and opts out after 2024. He’d certainly be betting on himself on a short-term deal.

While there’s always the risk that a short-term deal with an opt-out clause like the Snell contract means Montgomery walks after the season in search of a longer term contract, he would certainly provide a boost to a rotation missing its breakout star in Bradish from last season. He could also allow the team to trade John Means, who, like Burnes, is in his final year of arbitration and could become a free agent after the season.

Given his postseason track record, which also includes four innings of one-run pitching against the Rays in his lone start for the Yankees in the 2020 American League Division Series, surely Montgomery would also improve the O’s 50.8% odds of making the postseason, per FanGraphs. He also holds an impressive 16-8 record against AL East opponents in the regular-season and playoffs for his career, with a 3.58 ERA over 306.1 innings.

With a wealthy, new ownership group committed to bringing back a World Series to the City of Baltimore, let's hope general manager Mike Elias has been given the green light to go out and sign Montgomery to improve the starting rotation on a young team, with lots of arbitration and pre-arbitration eligible stars, and a distinct lack of longer-term contracts.

Even with an abbreviated spring training to get him ramped up, Jordan Montgomery would surely improve this roster in 2024, and provide valuable postseason and World Series experience both in the clubhouse and on the field.