Montgomery's $25m salary then won't really be an "albatross".
This is where we will have to disagree. The list of highest contracts ever given out to pitchers is littered with albatrosses. There are probably more horrible contracts on this list than players who lived up to them. And of the top 3 on the list, none will be able to start the season. Only 2 out of the top 8 were available for the playoffs last year. And I'm not sure Jordan Montgomery has ever had a season on par with the best of these other players. Just because he may be among the top 30 pitchers currently doesn't mean he is going to be worth ace money. Very few of the the top 30 pitchers ever really are.
Starting pitchers
The highest-paid starting pitchers, by average annual value:
1. Shohei Ohtani, $46,081,476 (2024-33) (reduced for deferrals)
2. Max Scherzer, $43,333,333 (2022-24)
… Justin Verlander, $43,333,333 (2023-24)
4. Zack Wheeler, $42,000,000 (2025-27)
5. Jacob deGrom, $37,000,000 (2023-27)
6. Gerrit Cole, $36,000,000 (2020-28)
7. Stephen Strasburg, $35,000,000 (2020-26)
8. Trevor Bauer, $34,000,000 (2021-23)
9. Justin Verlander, $33,000,000 (2020-21)
10. Zack Greinke, $32,500,000 (2016-21) (reduced for deferrals)
11. David Price, $31,000,000 (2016-22)
… Clayton Kershaw, $31,000,000 (2019-21)
13. Clayton Kershaw, $30,714,286 (2014-20)
14. Max Scherzer, $30,000,000 (2015-21)
15. Shohei Ohtani, $30,000,000 (2023)
16. Jacob deGrom, $27,500,000 (2019-23)
17. Tyler Glasnow, $27,312,500 (2024-28)
18. Yoshinobu Yamamoto, $27,083,333 (2024-35)
19. Carlos Rodón, $27,000,000 (2023-28)
20. Jon Lester, $25,833,333 (2015-20)
21. Justin Verlander, $25,714,286 (2013-19)
22. Chris Sale, $25,600,000 (2020-24)
23. Felix Hernandez, $25,000,000 (2013-19)
… Stephen Strasburg, $25,000,000 (2017-23)
… Jake Arrieta, $25,000,000 (2018-20)
… Justin Verlander, $25,000,000 (2022-23)
… Sonny Gray, $25,000,000 (2024-26)
28. Aaron Nola, $24,571,429 (2024-30)
29. Zack Greinke, $24,500,000 (2013-18)
30. CC Sabathia, $24,400,000 (2012-16)