There are terrible free agent signings, and then there is Jordan Montgomery's signing. Montgomery was a very late 2023 signee by Arizona after his hopes never materialized. The disrupted schedule helped contribute to an absolutely disastrous 2024. He did, however, pitch enough to get a $22.5M vested option for 2025, but he came down with elbow soreness which eventually required his Tommy John Surgery in April. Montgomery is now a free agent in the midst of his TJS recovery meaning no lucrative contract is coming his way this winter. It is very likely Montgomery gets one of those popular two-year backloaded deals where a new team is paying him to mostly rehab in year one so he can fully contribute in year two. This has been an unfortunately career arc for Montgomery after a three-year stretch from 2021-2023 where he bounced back from his first TJS in 2018. The best hope here is Montgomery has a 2027 similar to his 2021, but unless you are in a deep keeper league and want to stash him for $1, scratch him off your 2026 draft plans. Read Past Outlooks