Jury is still out on this one. We have no clue how valuable those picks are going to be and if they're not valuable (in other words not in the lottery) then we gave up two hall of famers for a bunch of garbage.
Also, the other moves you mentioned are very small scale moves that literally no one knows or remembers. Also 3 of the moves you referenced happened 9-11 years ago. I am talking about larger scale trades that have happened post KG. Picking up Nate was good but then Ainge traded him a
https://www.youtube.com/watch?v=2Oy6DwHAi70He has won plenty but your dislike of him has clearly clouded your perceptions. There is a reason other GMs are scared to deal with him. GM consistently identify him as one of the best out there, though after this off season, I am inclined to think Pop and SA have the best GM.
It takes understanding of the salary cap, to understand the depth of some of his moves. If you shallow measure them by player acquisition and can't see beyond that then I feel for you.
December 18, 2014: Traded Dwight Powell and Rajon Rondo to the Dallas Mavericks for Jae Crowder, Jameer Nelson, Brandan Wright, a 2015 1st round draft pick and a 2016 2nd round draft pick. (2015 pick is conditional. Boston also receives $13M trade exception.)
January 9, 2015: Traded Brandan Wright to the Phoenix Suns for a 2015 1st round draft pick (MIN 1st-Rd Pick was later selected). (The 1st round pick is top-12 protected in both 2015 and 2016. If the pick is still held in 2017 it will become two 2nd-round picks.)
January 12, 2015: As part of a 3-team trade, the Boston Celtics traded Jeff Green to the Memphis Grizzlies; the Memphis Grizzlies traded Tayshaun Prince and a future 1st round pick to the Boston Celtics; the Memphis Grizzlies traded Quincy Pondexter and a 2015 2nd round draft pick to the New Orleans Pelicans; the New Orleans Pelicans traded Austin Rivers to the Boston Celtics; and the New Orleans Pelicans traded Russ Smith to the Memphis Grizzlies. (Memphis will receive a traded player exception.)
January 13, 2015: Traded Jameer Nelson to the Denver Nuggets for Nate Robinson.
January 15, 2015: As part of a 3-team trade, the Boston Celtics traded Austin Rivers to the Los Angeles Clippers; the Los Angeles Clippers traded Chris Douglas-Roberts and a 2017 2nd round draft pick to the Boston Celtics; the Los Angeles Clippers traded Reggie Bullock to the Phoenix Suns; and the Phoenix Suns traded Shavlik Randolph to the Boston Celtics.
January 23, 2015: Signed Andre Dawkins to a 10-day contract.
February 19, 2015: As part of a 3-team trade, the Boston Celtics traded Marcus Thornton and a 2016 1st round draft pick to the Phoenix Suns; the Boston Celtics traded Tayshaun Prince to the Detroit Pistons; the Detroit Pistons traded Gigi Datome and Jonas Jerebko to the Boston Celtics; and the Phoenix Suns traded Isaiah Thomas to the Boston Celtics. (PHO 2016 1st round pick received from BOS is CLE's pick and is top-10 protected.)
Lots of picks in these trades, that will someday be players only then can we truly evaluate them. The brilliance is that almost all of them helped us slightly or got something for a guy who was no longer in our plans without giving up much.