Of course he does, as long as it makes sense to do so.
Maintaining some level of financial flexibility is important. Injuries happen - Jays sign Bauer and he needs TJS, salary is still on the books. Vladdy could hit 50 HR in 2021 and it makes sense to buy out some free agent years now.
Shatkins doesnt want to be reckless, and doesn't want to be too cautious either. It's a balance.