The problem with trading Pillar is that aside from Alford (who had a bad year), no one can play CF. Well, Grichuk can, but he doesn't rate very well over there. He's more likely to be a 2-3 WAR player in RF. An OF with Grichuk at CF and Teoscar anywhere else is likely to be awful. Although if they can trade Pillar and move Morales, then putting Teoscar at DH, Grichuk at CF, and finding an above average defensive veteran to fill one of the corners (with McKinney on the other) might be doable. Lose some defensive value with Grichuk, but it's only temporary until Alford is (hopefully) ready mid season.
The Jays will have a lot of OF's on the 40 man roster next year (Pillar, Grichuk, Teoscar, McKinney, Alford, Davis, Pompey, Smith Jr). They also may want to add Ramirez. Looks like Pompey is gone one way or another (wonder how long it takes Alex to bring him in?). There is going to have to be some movement there. THe Jays might be at the point where they have to make some Yankees types of trades (to clear 40 man clutter).