Pitino's coaching style wasn't meant for the pro game, but I think he improved a bit over time. And, I always appreciate how much hustle he had Paul Pierce playing with as a rookie.
The real problem with Pitino was the personnel moves.
https://www.basketball-reference.com/executives/pitinri99x.htmlI'm going to cut and past for those who don't want to click through:
June 25, 1997: Selected Chauncey Billups (1st round, 3rd pick), Ron Mercer (1st round, 6th pick) and Ben Pepper (2nd round, 55th pick) in the 1997 NBA Draft.
July 7, 1997: Signed Travis Knight as a free agent.
July 28, 1997: Signed Bruce Bowen as a free agent.
July 28, 1997: Signed Andrew DeClercq as a free agent.
July 28, 1997: Signed Tony Massenburg as a free agent.
August 21, 1997: Traded Eric Williams to the Denver Nuggets for a 1999 2nd round draft pick (Kris Clack was later selected) and a 2001 2nd round draft pick (Earl Watson was later selected).
August 22, 1997: Signed Chris Mills as a free agent.
August 22, 1997: Signed Tyus Edney as a free agent.
October 22, 1997: Traded Chris Mills, a 1998 2nd round draft pick (DeMarco Johnson was later selected) and a 2000 2nd round draft pick (Lavor Postell was later selected) to the New York Knicks for Scott Brooks, Dontae' Jones, Walter McCarty and John Thomas.
October 28, 1997: Traded Tony Massenburg and a 1999 2nd round draft pick (Obinna Ekezie was later selected) to the Vancouver Grizzlies for Roy Rogers.
February 18, 1998: Traded Chauncey Billups, Dee Brown, Roy Rogers and John Thomas to the Toronto Raptors for Kenny Anderson, Popeye Jones and Žan Tabak.
March 25, 1998: Signed Reggie Hanson to the first of two 10-day contracts.
April 14, 1998: Signed Reggie Hanson to a contract for the rest of the season.
June 24, 1998: Selected Paul Pierce (1st round, 10th pick) in the 1998 NBA Draft.
January 21, 1999: Traded Travis Knight to the Los Angeles Lakers for Tony Battie.
January 21, 1999: Signed Dwayne Schintzius as a free agent.
January 27, 1999: Signed Eric Riley as a free agent.
February 12, 1999: Signed Marlon Garnett as a free agent.
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.
April 14, 1999: Signed Damon Jones to the first of two 10-day contracts.
May 4, 1999: Signed Damon Jones to a contract for the rest of the season.
June 30, 1999: Selected Kris Clack (2nd round, 55th pick) in the 1999 NBA Draft.
August 1, 1999: Signed Adrian Griffin as a free agent.
August 3, 1999: Signed Wayne Turner as a free agent.
August 3, 1999: Traded Popeye Jones, Ron Mercer and Dwayne Schintzius to the Denver Nuggets for Danny Fortson, Eric Washington, Eric Williams and a 2001 1st round draft pick (Kedrick Brown was later selected).
August 5, 1999: Signed Calbert Cheaney as a free agent.
October 21, 1999: Signed Marty Conlon as a free agent.
November 8, 1999: Signed Doug Overton as a free agent.
December 13, 1999: Signed Jamel Thomas as a free agent.
June 28, 2000: Selected Jérôme Moïso (1st round, 11th pick) in the 2000 NBA Draft.
June 28, 2000: Traded a 2001 2nd round draft pick (Earl Watson was later selected) and a 2001 2nd round draft pick (Michael Wright was later selected) to the Seattle SuperSonics for Josip Sesar.
August 1, 2000: Signed Mark Blount as a free agent.
August 3, 2000: Signed Randy Brown as a free agent.
August 16, 2000: As part of a 4-team trade, the Boston Celtics traded Danny Fortson to the Golden State Warriors; the Boston Celtics traded Dana Barros to the Dallas Mavericks; the Dallas Mavericks traded Robert Pack, Hot Rod Williams and cash to the Boston Celtics; the Dallas Mavericks traded Bruno Šundov to the Utah Jazz; the Golden State Warriors traded Bill Curley to the Dallas Mavericks; the Golden State Warriors traded Donyell Marshall to the Utah Jazz; the Utah Jazz traded a 2001 1st round draft pick (Joseph Forte was later selected) to the Boston Celtics; the Utah Jazz traded Howard Eisley to the Dallas Mavericks; and the Utah Jazz traded Adam Keefe to the Golden State Warriors.
August 21, 2000: Signed Chris Carr as a free agent.
October 16, 2000: Traded Calbert Cheaney and Robert Pack to the Denver Nuggets for Chris Herren and Bryant Stith.
November 6, 2000: Signed Rick Brunson as a free agent.
December 6, 2000: Signed Milt Palacio as a free agent.
There were a couple of okay moves in there, but trading Chauncey and giving up a pick that could have been Andre Miller or Shaun Marion for Potapenko were just unforgiveable.
The one potentially excellent move he made (outside of drafting Pierce, which seemed obvious) was trading Mercer for Eric Williams, Danny Fortson and a #1. That #1 was special, because not only did it not have protections, but it had a "roll over" provision good for two drafts.
As we all know, we took Kedrick Brown with that pick. We had three picks that year, and the #11 could have been used on Richard Jefferson, Troy Murphy (heavily rumored), Zach Randolph, etc. (That draft was compounded by taking Joe Forte over Tony Parker, also heavily rumored).
But the real tragedy? With three picks in the draft, we should have rolled over the #11. Denver was terrible the next two years; we could have had the #5 pick in 2002 or the #3 pick in 2003. All of that is on Chris Wallace, though, rather than Pitino.
The patient, future-oriented Celtics:
Antoine
Marion
Carmelo
Pierce / Joe Johnson
Tony Parker / Chauncey Billups
In fairness, we probably don't roll over the draft pick twice. So, let's scrap Carmelo, and take Amare in 2002.
Amare
Antoine / Marion
Pierce
Johnson
Parker / Chauncey
All we would have need is Mike D'Antoni!