There's a lot of chatter around town regarding Theo's short-term future at the top of the Cubs and from my understanding it's all wasted breath. All indications point to him finishing up the last year of his deal and remaining president through the 2021 season. So on that front I wouldn't be worried that he runs out the back door this winter with so many decisions left to be made. That said, I'd expect a fairly transparent transition period once we get going into 2021 but that's a different blog for a different day. For now, I want to just be clear that Theo will be working on our problems this offseason. That's good news.
The first and arguably most impactful decision will be what to do with Jon Lester and his $25M club option against a $10M buyout. We've talked about this before but generally in the realm of it being a slam dunk decision to bring Lester back. The argument became less believable as 2020 progressed but there were still some really bright spots, like the fact that 5 of Lester's 10 best games since 2019 came in 2020 while only making 12 of the 43 total starts. His ability to shutdown a lineup this year was on par with any of his past Cubs' seasons.
But when he was bad, he was downright awful. A quarter of the time he couldn't get out of the 4th inning while velocity casually lived in the upper 80's. His swing and miss rate was a career low while Home Runs per 9 registered a career high. Every sabermetric in the universe tells you he's a liability and that's before I remind you a twenty five million dollar liability.
Even so I feel like the Cubs need to bring him back and cut the check. It's $10M to let him walk into free agency. Some of you have said to pay the buyout then "just bring him back on a friendly deal" like we're not talking about one of the most competitive athletes in Chicago's rich history. Like he would be Totally Cool with having his option declined in favor of a smaller salary because what? After his entire career Jon Lester is going to start being a bitch NOW? I don't think so. He didn't take Boston's discount and I can assure you he won't sign on as a player/coach to help the Cubs make their $220M payroll next year.
Instead I think the Cubs will see this as a $15M marketing campaign if Lester wants to retire after 2021. If this is his last season then the Cubs can definitely make some money off his image and likeness. Maybe get creative and let him start a farewell YouTube show with Dempster. Maybe give him a key to Sluggers in a real nice presentation in June so he can enjoy it the rest of the season. Like really blow the doors off on his way out and throw a party. Unless of course he doesn't want to retire after 2021 which in that case kinda fucks everything.
Or we could just rip the bandaid off and start rebuilding a new core and let's just say I'm not ready to keep writing this paragraph. My brain is still coming together from the Marlins. Your space is appreciated.