Cubs Rumors: Blue Jays eyeing both Kris Bryant and Kyle Hendricks

Chicago Cubs: Would anything surprise you at this point?

Given what we know about the Darvish trade, the Cubs look to be positioning themselves for much further on down the road than most fans would be happy with. With a haul of prospects who can’t even legally drink yet, it seems the Cubs might be aiming for 2023 or 2024 in a possible “reload” that would be a total rebuild if this comes to fruition.

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If you start looking around and surveying what the Jays have to offer in return, it’s clear that right-hander Nate Pearson is probably not the centerpiece guy. At 24, and ready to be a guy in Toronto this year, it wouldn’t make a lot of sense to go for it and then lose a guy who pitched in the postseason for them just a couple months ago. It also wouldn’t make sense for the Cubs to look ahead to four years down the road and lose several years of a good starter.

After Pearson, Toronto’s system does feature several younger players who may well be involved in any possible talks. Simeon Woods Richardson, the next highest-ranked pitcher in their system, only just turned 20 and would line up with what the Cubs seem to be doing. Woods is on the fast track to becoming a mid-rotation starter, possessing excellent command, a phenomenal two seam-runner and great athleticism. If this deal does happen, he might be one of the guys.