1. Stealing Jerami Grant from the Pistons
This deal with the Pistons was a low-risk, high-reward trade for Cronin and the Blazers, acquiring a borderline All-Star in Jerami Grant to pair alongside Damian Lillard. They needed to get Lillard more help than just Grant, which ultimately led to his trade request last offseason, but this deal for Grant was a step in the right direction and didn't sacrifice significant future assets in the process.
One concern when initially acquiring Grant was that the Blazers would have to sign him to a substantial contract—as evidenced by last summer's five-year, $160 million deal—despite him not being a primary or even secondary player who can lead a team to a deep playoff run.
While his deal is still likely an overpay, given Grant's' lack of impact as a playmaker (2.8 assists per game last season) and rebounder (3.5 rebounds), that has become less of an issue with the reported interest other teams, including the Lakers and Mavericks, have had in Grant this offseason.
Cronin's current asking price for Grant is reportedly two first-round picks, which seems too steep, given the factors previously mentioned surrounding his contract and inability to be a playoff team's go-to player. Regardless, the Blazers will likely get much more in return in a potential Grant trade than they gave up to acquire him from the Pistons, making this the biggest fleece of the Cronin era.