Deal is largely contingent upon Toronto remaining in the Playoff race in mid-late July. Toronto: Fill long-term CF void and give Bo and Vladdy reason to stick around with extensions. With no "future core" building in the minors, the Jays are better off trying to add onto the big league roster and entice the two homegrown guys to stay long-term. Kiermaier would move into a 4th OF role for the rest of 2024 and will be gone at the end of the season, freeing up $11M. Orelvis continues to slide further and further down the defensive spectrum and remains a hit tool risk. Kikuchi is an impending FA whose current rotation spot could (possibly) go to Tiedemann if he's ready in July. Milwaukee: Injury-ravaged rotation gets major infusion of help with two solid mid-rotation arms in Kikuchi and Fedde, the latter of whom can stick around for 2025, too. As of now, there just isn't enough pitching in Milwaukee to get the Crew through the rest of the season and Playoffs. Garrett Mitchell is a very difficult roster fit given the current roster construction and risks losing even more luster off of his Draft pedigree if he doesn't show something this season (returning from yet another injury). Still, he has some value and would be a plug-and-play starter for the ChiSox in CF or in either corner with several years of remaining control. Uribe has erratic command but an amazing arm -- a perfect high-upside ticket for the White Sox (similar to Prelander Berroa). Monasterio is a useful infield utility guy who can play several positions but is redundant in Milwaukee. ChiSox: Robert's contract runs through 2027, but unless they've assembled a legitimate core by the time his walk year rolls around, he's unlikely to re-sign again. Orelvis would infuse high-end talent into the lineup, and while his long-term defensive position remains in question, the ChiSox have all the time in the world to figure it out. Nimmala was Toronto's 2023 first rounder but looks light years away from being a big leaguer. Very raw and undeveloped (even for an 18 y/o) but a good fit for Chicago's current rebuild timeline.