That's not "risk tolerance"; it's ignorance.
Toronto could trade Giles at the deadline for a player or players who can contribute over the next ~6 seasons, then make a point to sign a lockdown RP in free agency before 21. The MLB team would be in substantially the same position for 2021, financially and in terms of talent, had they extended Ken Giles, but they would have ~47 exciting years of control over players in addition to that.
Your idea doesn't accelerate any process, in theory. It just misses out on value. It has nothing to do with optimism.
Are you Ken Giles or something?
Enough of this in my Mookie thread though.