4 players the Cubs should keep/trade - Owen Caissie (trade)
Owen Caissie enjoyed a fantastic breakout season offensively in Double-A Tennessee last season, where he played for the entirety of the year. He slashed .289/.398/.519 with 22 homers, 77 RBIs, and a 144 wRC+. He excelled in taking walks but registered a high strikeout percentage of 31.1%.
If he is not moved this winter, it's easy to see him starting in Triple-A this year, and from there, he could be a call away if there are any types of injuries. Besides Crow-Armstrong and Alexander Canario, he is the next closest of the outfield prospects to the MLB level.
Even more so than other outfielders on this list, Caissie's future in the outfield is questionable if he’ll stick there defensively. The possibility of him moving to first base if it doesn’t work out has been discussed. Although Michael Busch isn’t a lock to remain there long-term unless he is entirely unsuccessful, it seems unlikely Caissie would have a spot at 1B where Cody Bellinger can also play if he is re-signed. Therefore, he’s blocked at every position for the moment. His bat offers high upside, but he has no clear path to the majors unless several things don’t work out first.