Now that the off-season is (finally) over, I think I would give the Cavs a solid A- for their off-season.
From what I have seen in the national media -- I'm talking just the reasonable ones -- my sense is the Cavs' off-season has been a bit under-appreciated.
It's revisionist history for them to assume Love re-signing was a done deal, as many seem to imply.
The fact is that most of the key players on the team were free agents, retaining them all was going to represent a huge financial commitment, and I don't think any reasonable analyst could have faulted them for making some budget cuts, despite being close to a championship.
So bringing Love, Shumpert, Thompson, Smith, and Dellavedova all back at a price the Cavs were willing to pay is significant. Thompson is a possible partial exception, since (based in part on Pluto's reporting) there is some reason to believe the Cavs moved more in Thompson's direction than was initially thought (and reported by reputable reporters such as Woj, Stein, Windy, and others).
Getting LeBron to recommit early in the process was huge (even if they don't deserve much credit for what LeBron chooses to do).
Adding Williams and Kaun on the mini MLE would seem to be good value, though this remains to be seen. Mo is on the downside of his career, and Kaun is unproven and (at best) limited. Merely showing a willingness to use the mini MLE showed a commitment to winning.
Whether Mo meets the team need for another playmaker (a need identified by Griffin after the season) is somewhat debatable, but I think there is a good argument that the Cavs couldn't have hoped to have done better. Mo wanted to return and the Cavs got it done, though I don't think they necessarily got him at a steep discount (as some such as Chris Haynes apparently believes).
With Kaun, I personally would have preferred an NBA free agent like Tyler Hansbrough or Jeff Withey (both of whom signed for the minimum), but can at least understand that Kaun has the size and girth to be a reasonable facsimile for Mozgov if necessary, so I will withhold judgment.
Adding Richard Jefferson for the minimum looks like a solid move. At this time, I don't see an obvious opportunity cost with this move. It's slightly alarming that LeBron's primary backup is 35 years old, but you can't have everything. James Jones is also back, of course.
While some will disagree, I think punting on their first round pick made some sense, given who was still on the board at that time. Ending up with Rakeem Christmas, who they would almost immediately turn into a second round pick 4 years down the road, must be counted a poor outcome. They did get Cedi Osman in the deal dumping the first round pick, and he at least seems to have some value.
Other than punting on their first rounder, the only cost-cutting move so far was moving the Mike Miller contract, which also netted them the Haywood TPE. I think this deal was well-executed, and ensured they had one less piece of deadwood on the bench this year (no offense to Mike Miller who had a very good career).
The Haywood chip/TPE was not used, but in my mind this only made sense if they had been replacing one of their free agents. Since they all returned, I just don't think it would have been reasonable to expect them to add even more salary. They then converted Haywood into the TPE at a reasonable cost, retaining this asset.
Most of all, David Griffin showed admirable restraint and patience. At various times, he could have panicked, especially with an owner/boss known for his impatience. He waited out JR, struck early with Love/Shump, and of course waited out Tristan/Rich Paul. He took his time on the inevitable Haywood deal, and now has the protection afforded by the TPE through the end of July 2016.
All the free agents rumored to be of interest to the Cavs -- guys like Rodney Stuckey -- just weren't realistic given what the Cavs could pay. David West is a possible exception, but he only made sense if the Cavs could have pulled off a Varejao for Joe Johnson deal. Hard to know for certain whether the Cavs backed out of that deal or the Nets did (I tend to think the Nets did, but I could be wrong), but regardless it's important to realize that had the Cavs done that deal, it's not reasonable to believe they would have retained JR Smith as well. I mean, I would prefer having West/Johnson over Varejao/Smith, but again it's not certain the Johnson deal was actually on the table, and with Varejao looking good this preseason (yes, I know), maybe the difference here isn't as big as it looked back in July.