The outfield is not deep at all.
Verdugo 3.0 WAR
Yoshida 1.4 WAR
Duran 1.4
Yoshida can't field, his defense is horrible.
Duran has been up/down, exciting player but he's had two good months and then a lot of subpar play, he could turn back into a pumpkin or just be a 1.5 WAR player.
Dugo, good player but not great and gone after 2024.
After that you have role players and bench bats, the best of which Duval is also a FA at the end of this year.
Wong/McGuire at Catcher and Teel looking like he's on the fast track. Casas after slow month has turned into one of the best hitters in all of baseball and 1B. Arguably MI is as weak, but if Story is healthy the outlook looks a lot different, especially if Rafaela actually spends time there (making of even weaker) and Reyes and Urias can field their positions and Luis has good offensive upside as well.
The outfield has zero depth. What happens if you lose an outfielder and trade Dugo and you're rolling out with Yoshida/Ref/Abreu next year? That could literally be a disaster.
You also have a better prospect pipeline closer to the majors up the middle than you do in the OF.
I will not answer the question in your statement because I have a very strong preference to NOT trade any of those guys, including Dugo and any of the guys in the outfield.