Right now:
Semien leads the LEAGUE for batters with a 6.1 WAR
Ray is probably a top 3 Cy Young candidate.
Both are going to be needs going forward. Both are having outstanding seasons. Both have taken their games to new levels as Jays. Both are going to get paid.
But going forward, we have to keep in mind our core young players that will be arb eligible soon and you probably want to lock up long term. Is there a risk in backing up the dump trucks full of cash to Semien (31 soon, maybe he'll want to sign somewhere to play SS?) and Ray (does he repeat this caliber of season) with the risk of not being able to afford extensions to others?
Both would leave huge holes in the lineup and rotation.
Do you prioritize one over the other? Do you try signing both? Do you let them walk? What are the short and long term consequences and risks?