Unlike "grading" the draft, you actually have something to go off of when grading trades, free agency and the offseason in general. There's obviously no guarantee that a player acquisition is going to work out simply based on past performance, but it's certainly a more reasonable extrapolation than guessing how the NBA career of someone who has, by and large, never played against grown men is going to pan out. When it comes to free agency and trades, at least there's some prior experience to draw upon.
So while nobody knows what the future holds (a statement that probably goes triple for 2020), keen observers can draw some reasonable conclusions about how well a current NBA player will fare with a new team. With that typed, here's some of the national perspective/grades regarding the Trail Blazers adding Robert Covington, Enes Kanter, Derrick Jones Jr. and Harry Giles III and re-signing Rodney Hood and Carmelo Anthony in the last week...
• Bobby Marks of ESPN has been bullish on the Trail Blazers since the team acquired Covington from Houston, and it seems as though he's liked everything else as well since...
• Zach Lowe, also of ESPN has the Trail Blazers (one of his two "feel good bubble story" teams) as one of his winners of the 2020 offseason...
• A both Matt Dolinger and Justin Verrier at The Ringer have the Trail Blazers as their "winners of the offseason" thus far...
• Dan Devine, also at The Ringer, listed the Covington trade with the Rockets as his favorite move so far...
• Micael Shapiro at SI.com gives Portland an "A" for their offseason acquisitions...
• Duncan Smith at Fansided is handing out grades for every free agent signing. So far he gives the re-signing of Carmelo Anthony on a one-year deal a "C"...
As for re-signing Hood and outright signing Derrick Jones Jr., Smith hands out two "C-"...
• Charles Curtis at For The Win gives the Trail Blazers a "A" for their handling of the shortened 2020 offseason...
An already-contending squad gets a key reserve in Enes Kanter, re-signs another bench stud in Rodney Hood, trades for defensive expert Robert Covington and grabs an intriguing piece in Derrick Jones. Oh and MELO IS BACK. You get an A!
• Grant Hughes at Bleacher Report gives the Trail Blazers an "A-" for the Covington trade...