With rotation depth crumbling, the San Diego Padres should gamble on a lefty reclamation project for a low-risk, high-reward boost.
The San Diego Padres have one of the most well-rounded rosters in baseball, but there are still some areas that need some adjusting before the 2026 season kicks off if the hope is to improve on last season’s 90 wins.
The infield is a big question mark for San Diego, but the biggest question of all comes in the starting rotation. As it stands, the Padres have a solid four-man rotation, but it falls off considerably when reaching the fifth or sixth man. With Yu Darvish out for the 2026 campaign and Dylan Cease leaving for the Toronto Blue Jays, the Padres are yet to fill in for their absences.
Because of this, it’s no surprise that Bleacher Report’s Kerry Miller selected starting pitching as the biggest area of need for the Padres. To fill this need, Miller tabbed left-handed starting pitcher Jordan Montgomery as the final piece of the starting rotation in San Diego.
Montgomery didn’t pitch in 2025 after undergoing Tommy John surgery, making him one of the most intriguing free agent pitchers available this winter. His last time out on the mound in 2024 wasn’t all that impressive, posting a 6.23 ERA in 117 innings for the Arizona Diamondbacks.
For a few years prior, however, Montgomery was one of the better starters in baseball. In 2022 and 2023, the lefty recorded ERAs of 3.48 and 3.20, respectively. With his bad showing during his last season on the mound and returning from Tommy John surgery, Montgomery won’t exactly have teams ready to throw tons of money at him this winter.
With a market value estimated at around $2.6 million AAV, Montgomery could prove to be a buy-low option for a team like the Padres. San Diego’s rotation will already have one spot occupied with a Tommy John-retuner in Joe Musgrove, but Montgomery could provide some much-needed depth to a very thin starting rotation.
Given the current financial situation the Padres are facing, they may have to resort to low-cost reclamation projects, and Montgomery is just that. Even if Montgomery returns in 2026 as a league-average starter, it’d be a win for the Friars. With the current rotation’s lack of left-handed arms, Montgomery could provide even more value. If the 33-year-old ends up not being able to return to the level he was at a few seasons ago, the Padres could live with the few million it would have to eat.
He might not be the first name you think of when looking at free agency starting pitchers, but Montgomery has low-risk, high-reward written all over him. General manager A.J. Preller has flashed his magic in the past, and taking a chance on Montgomery could be another trick in his vast collection.