Nice summary of Pitino's moves as a GM:
https://www.basketball-reference.com/executives/pitinri99x.html#:~:text=Boston Celtics Franchise (May 6,Bowen as a free agent.
Let's focus on just the 1st round picks, as the 2nds are all inconsequential:
June 25, 1997: Selected Chauncey Billups (1st round, 3rd pick) and Ron Mercer (1st round, 6th pick) in the 1997 NBA Draft.
* Billups was undoubtedly a good pick, even if he needed time to season. Ron Mercer...was not.
June 24, 1998: Selected Paul Pierce (1st round, 10th pick) in the 1998 NBA Draft.
* An all-time steal. I remember sitting there going "why is this Pierce guy dropping?". He was then not traded. This was a good move!
March 11, 1999: Traded Andrew DeClercq and a 1999 1st round draft pick (Andre Miller was later selected) to the Cleveland Cavaliers for Vitaly Potapenko.
* Andre Miller...we coulda had Andre Miller paired up with Pierce and Walker.
June 28, 2000: Selected Jérôme Moïso (1st round, 11th pick) in the 2000 NBA Draft.
* This now puts to rest any suggestion that Pitino "actually drafted great". He had 5 top 11 picks in 4 years, made bad calls on 3 out of 5. The trade of Billups is just icing on the cake that Pitino was a terrible executive.
Trading Billups wasn't the problem, he was basically injured/ineffective for
years. He didn't even start to pan out until his third team/5th season. It was on Detroit in year 6 of his NBA career where he became a solid/good player. I'd argue that passing over Tracy McGrady
twice was a much bigger problem than drafting Mercer or trading Chauncey. The Billups trade wasn't even terrible as Kenny Anderson was pretty good for them (and Billups wouldn't have been).
Even the Mercer selection
could have worked out as Pitino made a pretty good deal when he moved him to Denver for Danny Fortson and a future first. Unfortunately Chris Wallace just
had to use that #1 in 2001 to select Kedrick Brown (a mistake he compounded when he elected to maintain a death grip on Brown in the Rogers/Delk trade, sending the Suns Joe Johnson rather than Brown/Forte). Had he waited one more year Boston could have selected Caron Butler or Amar'e. Two more years and they could have added Bosh to Pierce.
What
really made the whole thing a killer was that they later moved Fortson for a 2001 #1. They'd promised to use the pick to two different players, thinking that only one of the would be available. As it turned out they both were, but Wallace used the pick on Joe Forte anyway (and then blamed Red after hearing the boos). But Tony Parker would have looked good in Celtics Green, as would Agent Zero (Arenas playing the 1 spot for Jim O'Brien would have been insane fun).
Also, you forgot the worst part about the Potapenko trade, the pick was unprotected (at a time when teams had just started protecting picks) and when he was asked about it during the presser the Ricktator said something along the lines of "We're going to be in the playoffs, not the lottery". Also, while the Cavs got Dre' Miller out of it, Shawn Marion was on the board at the time, and being able to slot him in between Walker and Pierce would have given the O'Brien teams a real shot.