They've also had some pretty clear wins though:
Hutchison for McGuire and Liriano
Liriano for Teoscar
JB Woodman for Aledmys Diaz, who in turn got traded for Trent Thornton
Grichuk for Leone and Conner Greene (extension may not have been the wisest move, but the initial trade was definitely a win)
These aren't superstar acquisitions that have provided a ton of surplus value by any means, but they still made the team markedly better while trading away little to almost nothing in value. The one huge trade they were able make where they had a significant amount of leverage, I think in retrospect has aged incredibly well (Stroman for Kay and Woods-Richardson).
There also may have been a been a mandate from ownership to make sure Osuna never suited up as a Jay again.
They've made some questionable trades, but I don't think the Osuna one is one of them.