Montgomery helped a team win the World Series, which means that his market will be quite steadfast. No team can ever have enough starting pitching, especially a good left-handed starter like Montgomery. The question is, where should he go?

A few teams stand out as possible options for Jordan Montgomery in free agency.

Baltimore Orioles

The Baltimore Orioles may not need starting pitching help in the worst way, but adding an additional arm to bolster their starting rotation would be quite prudent. Their starting pitching got lit up by the Texas Rangers in the postseason, and that followed a trend that began back in the regular season. The Orioles did fair well in team pitching statistics during the regular season; they ranked seventh in the league in ERA (3.89), 13th in strikeouts (1,431), 12th in opponents’ batting average (.242), and eighth in WHIP (1.24). The Orioles may have fared well in these metrics, but dig a little deeper and those numbers are skewed a bit by Baltimore’s robust bullpen.

The Orioles had only a single starting pitcher to make at least seven starts and pitch at least 30 innings to post an ERA below 3.60: that would be Kyle Bradish, who ended the 2023 season with a sparkling 2.83 ERA. Tyler Wells was the only other Orioles starting pitcher that hit those thresholds and posted an ERA below four in 2023.

Baltimore is ready to contend. They won the second most games in the league in 2023; only the Atlanta Braves won more games in the regular season. Their offense scored the seventh-most runs in 2023 behind only the Braves, Los Angeles Dodgers, Texas Rangers, Tampa Bay Rays, Houston Astros, and Chicago Cubs, the only team of this bunch who did not make the playoffs in 2023. Their payroll was the lowest in the sport in 2023, meaning they have money to spend if they’re willing to do so. They should be willing because this team is good now and needs help with their starting rotation badly. Jordan Montgomery would help them out immensely.

Arizona Diamondbacks

From one team that the Texas Rangers beat in their run to the World Series to another. The Arizona Diamondbacks began the 2023 season on fire but did slow down in the second half, clawing their way into the playoffs. But, the Diamondbacks got hot at the exact perfect time and took down the Milwaukee Brewers, Los Angeles Dodgers, and Philadelphia Phillies en route to the Fall Classic.

That World Series appearance came in spite of their pitching. In the regular season, the Diamondbacks ranked 20th in the league in ERA (4.48), tied for 23rd, ironically with the Texas Rangers, in strikeouts (1,351), 20th in opponents’ batting average (.251), and 19th in WHIP.

The Diamondbacks weren’t great on a team level and also didn’t get many great performances on an individual level. In the regular season, only two starting pitchers for the Diamondbacks posted an ERA below four in the regular season: Zac Gallen (3.47) and Merrill Kelly (3.29). In the postseason, it was only Kelly and Brandon Pfaadt who hit that mark.