What were the worst trades in Celtics history? Ranking the Top 10
Beyond their 17 title banners, maybe the one thing the Boston Celtics are best known for is their propensity for poaching talent in trades.
Earlier this month, we ran down the top 10 swaps in team history. But not every deal is a winner, as the Rick Pitino era seemingly sought to stress.
So here’s 10 of the worst trades in Celtics history.
Celtics Top 10: PG | SG | SF | PF | C | Most Clutch | Most Influential | Best Trades | 'Last Dance' seasons
10. Danny Ainge
Feb. 23, 1989: Celtics trade Danny Ainge and Brad Lohaus to Sacramento for Joe Kleine and Ed Pinckney
Ainge, only a season removed from his lone All-Star nod, was losing his starting role to 22-year-old Brian Shaw when he got moved to Sacramento for a pair of younger frontcourt players. Kleine was a better rebounder but was essentially Lohaus 2.0. Pinckney ended up playing six seasons in Boston but averaged an underwhelming 6.1 points and 5.3 rebounds per game at the tail end of the Big Three era.
9. Kendrick Perkins
Feb. 24, 2011: Celtics trade Kendrick Perkins and Nate Robinson to Oklahoma City for Jeff Green, Nenad Krstic, and a 2012 first-round pick (Fab Melo)
We already spent a lot of time on this one recently for our Hindsight 2020 series so we won’t belabor this too much here.
Yes, the deal made all the sense in the world on paper. And, yes, there were factors largely outside the team’s control in the aftermath (Green missed all of the 2011-12 season with a heart issue while Boston’s remaining core made its last true run). Still, in the land of Danny Ainge home runs, this was an infield single at best.
8. Bob McAdoo
Feb. 12, 1979: Celtics trade Tom Barker and three 1979 first-round picks (Bill Cartwright, Larry Demic, Sly Williams) to New York for Bob McAdo
McAdoo was a seven-time All-Star averaging 27.8 points per game for his career entering the 1978-79 season. New York flipped him to Boston for a massive haul of first-round picks in a draft that was headlined by Magic Johnson. This one would have been much higher up the list if Demic (the 9th pick) or Williams (the 21st pick) weren’t unremarkable NBA players.
But the third pick used on Cartwright could have delivered someone like Sidney Moncrief to Boston. McAdoo only played 20 games in green but, salvaging the deal, he got flipped to Detroit for the pick that ultimately keyed the Kevin McHale/Robert Parish deal with Golden State.
7. Charlie Scott
May 23, 1975: Celtics trade Paul Westphal and two second-round picks (Jimmy Dan Conner, Butch Feher) to Phoenix for Charlie Scott
Scott was a five-time All-Star coming off a season in which he averaged 24.3 points per game when he arrived in Boston. His scoring dipped, but it’s hard to quibble with the results when the Celtics won a title in his first season (defeating Scott’s former team, no less).
The downside: Scott lasted little more than two seasons before being dealt to Los Angeles in 1977. Westphal blossomed into a five-time All-Star and future Hall of Famer in Phoenix.
6. Raef LaFrentz
Oct. 20, 2003: Celtics trade Antoine Walker and Tony Delk to Dallas for Raef LaFrentz, Chris Mills, Jiri Welsch, and a 2004 first-round pick (Delonte West)
You’ll find this one higher up on most lists than it probably deserves to be. This one hurt more in the moment than it does in hindsight.
Walker was coming off two All-Star seasons and was part of Boston’s surge to the 2002 Eastern Conference Finals. But, after taking over as general manager, Ainge started his overhaul by moving Walker to Dallas and taking on the bloated contract of injury-slowed LaFrentz.
It was the 2006 flip of LaFrentz to Portland that acquired some of the key parts that helped bring Kevin Garnett to town a year after that.
5. Picks that could have been Malcolm Brogdon
June 23, 2016: Celtics trade two second-round picks (Deyonta Davis, Rade Zagorac) to the Clippers for a future first-round pick
Entering the 2016 draft, Ainge was intrigued by University of Virginia guard Malcolm Brogdon, who was still on the board as the Celtics entered the second round of the draft with the Nos. 31 and 35 picks.
Alas, having drafted a point guard the year before (Terry Rozier) and worried where another guard would find playing time behind Marcus Smart and Avery Bradley, Ainge peddled those two picks to Los Angeles for a future first. Brogdon went to Milwaukee at No. 36.
It wasn’t a bad move but watching how Brogdon developed makes it a great “What if?”
4. Joe Johnson
Feb. 20, 2002: Celtics trade Joe Johnson, Randy Brown, Milt Palacio, and a 2002 first-round pick (Casey Jacobsen) to Phoenix for Tony Delk and Rodney Rogers
The Celtics were in a six-year playoff drought when a glimmer of hope emerged during the 2001-02 season. Paul Pierce was blossoming into an All-Star. Walker was launching 3s and wiggling all over the place.
Boston sacrificed the future by dealing Johnson for a pair of vets. The Celtics surged to the conference finals with both Delk and Rogers aiding that quest. Alas, Rogers was a rental. Delk hung around one more year before being dealt.
All while Johnson blossomed into a seven-time All-Star who made the playoffs 13 times with six different teams.
3. Vitaly Potapenko
March 11, 1999: Celtics trade a 1999 first-round pick (Andre Miller) and Andrew DeClercq to Cleveland for Vitaly Potapenko
The Celtics punted away the No. 8 pick in the 1999 draft for a lumbering big man who averaged 6.7 points and 3.5 rebounds in his first two-plus seasons in the league. They then compounded matters by giving Potapenko a SIX(!?)-year extension for $33 million.
That pick could have been Miller, Shawn Marion or Jason Terry. The Ukraine Train averaged 7.5 points and 5.8 rebounds while starting less than half of his 273 games in green before being dealt away as part of an even worse deal …
2. Vin Baker
July 22, 2002: Celtics trade Kenny Anderson, Joseph Forte, and Vitaly Potapenko to Seattle for Vin Baker and Shammond Williams
It’s easy to forget just how darn good Baker was early in his NBA career with four All-Star nods and two All-NBA appearances. Then the lockout happened in 1998. Baker emerged out of shape, and his production plummeted.
Despite a whole bunch of red flags, the Celtics traded for him, bringing him back home to New England. Amid underwhelming play, Jim O’Brien smelled alcohol on Baker's breath leading to his eventual release in 2004.
Baker’s career in Green: 7.7 points and 4.6 rebounds over 89 games.
1. Chauncey Billups
Feb. 18, 1998: Celtics trade Chauncey Billups, Dee Brown, Roy Rogers, and John Thomas to Toronto for Kenny Anderson, Popeye Jones, and Zan Tabak
Less than eight months after nabbing Billups with the No. 3 pick in the 1997 draft, the Celtics dealt the future five-time All-Star to Toronto for an underwhelming return.
The deal is the poster child for all that was wrong with the impatient and misguided Rick Pitino era. Billups got only 51 games in green before PItino made the move for veteran Anderson. The Celtics won 36 games that year and finished 12th in the Eastern Conference.
By 2004, Billups was Finals MVP with the Pistons and earning his “Mr. Big Shot” nickname.