Ewww I hope not. If the team can't make his salary work straight up in 2019 then just let him go. It's already worrisome that the 2020 Cubs are locked into Lester, Darvish, and Chatwood for a combined $60 million (includes Lester's 2021 buyout). I don't want to add 36 year old Cole Hamels at ~$15m to that. Eh, if it can save them ~$5 mil on AAV for LT purposes it might be worth it to do like 2/26 on Hamels (assuming the hit is $20 and not $14 like some think, if it is $14 then just exercise the horsefeathering option). If Chatwood is pitching on this team in 2020 it’s because he figured it out, IMO, he’s only making ~$12 mil and if he’s not producing he won’t have a spot. I still have highish hopes for Darvish over the next ~3 years and think he’ll be plenty valuable this year and next ~2. Lester might be awful but we all knew that was likely the case come 2020 on that deal. Hopefully Adbert or someone else internally/through trade is ready to step in by 2020 if needed. If things are so tight they need to extend him just to save $5m, then just let him walk and save the full $20m. I like Hamels for 2019, but he's a luxury. If Theo needs to be captain efficiency this winter to make Bryce work (totally fair, IMO), then the rotation is best addressed via trades and depth and not via money. The problem with the rotation isn't the specific guys, it's being locked into yet another player with significant guaranteed money. We all were drooling about this rotation at this time last year, and now they look...pretty good, I guess? What is this same group of guys going to look like next year? Because they're pitchers, smart money says the answer is almost certainly "worse." Worse probably doesn't mean bad, but it does leave something to be desired. Fulfilling those desires will be that much harder with Cole locked into a rotation slot and PTR's wallet being $15m lighter.