I'm arguing with myself. *IF* you add a pitcher, he replaces Assad. Maybe that's strategic? Send Assad, Brown, Hodge, Wiggins, Wicks, Little, and Neely to Iowa as nice option-able contingencies. .
Makes baseball sense to me to replace Assad with Gallen. Yes, Assad may just be as good or better a pitcher; but also possible that Gallen might just be better, perhaps significantly so. If Jed were to sign Giolito or Bassitt or Littell, the same reasoning would need to apply. Are those guys even as good or better than 3.45-career-ERA Assad, or with the Cubs defense and Wrigley will they actually be definitely better? Even if replacing Assad is a lateral move or a downgrade, does adding an Assad-quality guy available at Iowa make it more than worth it?
Scherzer, Nick Martinez, Aaron Civale, I kinda by then it's a no-brainer. Those guys are worse, and you're downgrading the big-league staff too much to replace Assad with one of them.
With the current roster, if healthy we've got 13 pitchers. Ten guaranteed big-league contracts and can't be optioned, only 3 or 4 have options: Horton, Palencia, and Assad. (Maybe Cabrera). Either way, Horton, Palencia, or Cabrera aren't guys you want to send down to make room for Nick Martinez or Max Scherzer.
So pretty much Assad is the top-13 pitcher that you might option. *IF* you want to sign an additional pitcher, it's to displace Assad on your preferred opening roster.