I've come to the realization that the best move with respect with Giles is likely to move him at the trade deadline, and then sign him back in the off-season. If he likes the Jays as much as he has stated then there should be no issue with getting him resigned at that point, just like the Yankees did with Aroldis Chapman. Unfortunately you'll likely never see another team stupid enough to move a prospect like Gleyber Torres for half a season of a reliever ever again, but Giles if healthy should be able to net back a nice prospect. You might end having to pay a little more to keep Giles compared to a pre or mid-season extension, but this way you have another hopefully nice prospect+Giles as well, think of it as using cash to buy a prospect.