One of the considerations is when is the next realistic contention timeline. 2020 is Martin expiration, 2021 is Tulo expiration. Also ETA of Guerrero. Stro/Sanchez/Osuna/Travis will still be close to peak, health permitting. Extending a couple of these guys past 2020 at less than market rate helps set up the Jays to field a very competitive team from 2020 on. There is risk of course, but running a baseball team is inherently about risk.