Cashman when Stroman was a Cub: Not trading for him, he wouldn't make our stating rotation
Cashman when Stroman was a free agent: Signs him
Cashman in a critical 5 game series: Leave him off the roster
Cashman in the 7 game ALCS if they advance: probably wants him as swing man
Not sure how Stroman's ego will handle this
Edit: yeah, with his recent performance he may be done for the year