1) Elgin Baylor, Clippers (1986-2008)

One of the themes of this list will be difficulties in separating a general manager’s mishaps from the whims of his miserly or otherwise incompetent owner. Baylor is the ultimate example of that dichotomy, as he was obviously constrained by the avaricious longtime Clippers owner Donald Sterling but also made his own fair share of mistakes even when unshackled from Sterling’s influence. Exhibit A is the NBA Draft, where in two-plus decades Baylor wasted lottery picks on busts and also-rans like Danny Ferry, Bo Kimble, Lamond Murray, Lorenzen Wright, Darius Miles, Yaroslav Korolev, Melvin Ely, and, most egregiously top overall pick Michael Olowakandi. Add that together with Sterling’s refusal to ink free agents to fair contracts and you have a 22-year tenure for Baylor that included just four playoff appearances, with only one series win in 2006. That one successful year, spearheaded by wise acquisitions of Elton Brand, Sam Cassell, and Cuttino Mobley, did earn Baylor the Executive of the Year award for ’05-’06 but things fell apart quickly again after that, eventually leading to his 2008 dismissal. Baylor later sued the Clippers, claiming he was fired due to agism and racism but lost in court. It was an appropriately acrimonious and unsatisfying end to a laborious era.

2) Billy King, 76ers (1998-2007)
3) Billy King, Nets (2010-2016)

Any debate about the worst general manager in NBA history wouldn’t be complete without considering King, who botched not one but two prime opportunities to guide a burgeoning franchise into long-term success. As a player, King was one of the early stars under Coach K at Duke (he supposedly later recruited his former college coach to replace Larry Brown in Philadelphia, unsuccessfully) and he spent some time as an assistant coach with the Pacers before reaching the 76ers front office in 1997, first as vice president and later as general manager. Under his guidance, the Sixers did reach the 2001 NBA Finals behind MVP Allen Iverson but King made a series of disastrous moves in the aftermath of that season. This included massively overpaying role players like Eric Snow and Kenny Thomas while repeatedly trading for past-their-prime chemistry disruptors like Derrick Coleman, Glenn Robinson, and Chris Webber. All of this put Philadelphia well over the salary cap and eventually forced King to trade Iverson to Denver for pennies on the dollar. Why the 76ers ownership allowed him to steward that important trade just to fire him less than a year later is a mystery but King somehow got another chance with the Nets in 2010. Given carte blanche by then owner Mikhail Prokhorov to spend whatever it took to be a contender, King got straight to work, swinging one disastrous trade after another, building a roster of creaky veterans that were all well past their All-Star level primes. The most egregious was his notorious 2013 deal with the Celtics, giving up four first round picks for a 37-year-old Kevin Garnett, a 36-year-old Paul Pierce, and a 36-year-old Jason Terry. King was finally “re-assigned” within the organization and then unceremoniously fired soon after.

4) Scott Layden, Knicks (1999-2003)

A son of coaching royalty, Layden got his start in the NBA as an assistant under his father, Frank, with the Jazz and was considered the organization’s top advocate for drafting John Stockton and Karl Malone. That pedigree eventually got him an opportunity in 1999 as general manager of the Knicks, who were not just one of the league’s premier franchises, but were coming off an NBA Finals appearance. His first major move was trading away Knicks franchise legend Patrick Ewing, which in and of itself was a prudent move (Ewing was washed up and asking for a contract extension) but the return was a disaster, bringing back the impractical contracts of Glen Rice, Luc Longley, and Travis Knight. Layden then made things even worse, signing Allan Houston to a contract so heinous ($100 million over six years) that the NBA later instituted the “Allan Houston Rule” to allow the Knicks to negate it. From trading Marcus Camby and Nene’s draft rights for a washed up Antonio McDyess to overpaying Kurt Thomas to drafting Mike Sweetney ninth overall, Layden crammed a lot of blunders into his three-plus years in New York before owner James Dolan fired him in December of 2003. His last major move was giving a two-year contract to Dikembe Mutombo, who was 37 years old at the time. One thing Layden arguably has going for him is he wasn’t as bad as his successor, Isiah Thomas.

5) Don Delaney, Cavaliers (1980-1983)

When new team owner Ted Stepien asked Delaney, then a professional softball coach and previously a basketball coach only at the high school and community college level, to be general manager of the Cavaliers, the initial answer was supposedly “you want me to do what?” This was the beginning of a friendship that was anything but beautiful between one of the most tightfisted and openly racist owners in NBA history and one of the most overmatched general managers. Delaney deserves only so much blame for what went down in those years, as it was Stepien calling the shots, which included trading away five consecutive first round picks in a superstar talent-laden era of NBA Draft history. In fact, those picks got turned into James Worthy, Dennis Rodman, Derek Harper, Sam Perkins, and Detlef Schrempf and could have been even more lucrative. Stepien also forced a race-based player quota on Delaney, refusing to allow too many white or Black players to be signed, drafted, or acquired via trade. In addition to his discomfitures as GM, Delaney also did a stint as Cleveland’s coach, compiling a 4-11 record during the ’81-’82 season before returning to only front office duties. The embattled Delaney, who had grown up in the Cleveland area, made the best of it, becoming something of a good faith ambassador for a franchise that seemed to be otherwise actively antagonizing its fans and local media. He was finally let go when Stepien was forced by the league to sell the team in 1983 and transitioned into a more idyllic lifestyle, opening a dive bar called Delaney’s Chase Inn in nearby Mentor, Ohio.

6) Rob Babcock, Raptors (2004-2006)

It’s never a good sign when your hiring as general manager goes against the appeals of the franchise’s already disgruntled star. This was the impossible situation that Babcock entered with the Raptors in 2004, when he was chosen over Vince Carter’s personal preference, Julius Erving. But Babcock did himself no favors in the aftermath. In fact, his first decision as GM was his worst, inexplicably selecting Rafael Araujo with the eighth pick in the 2004 draft over Andre Iguodala. He then overpaid free agent Rafer Alston, who managed to immediately render team chemistry somehow even worse. But Babcock’s signature transaction in Toronto came in December of 2004, when his inevitable trade of Carter turned out worse than even the most cynical Raptors fan could imagine. He sent his discontented star to the Nets in exchange for two overpaid role players (Aaron Williams and Eric Williams, no relation), a washed up Alonzo Mourning (whom the Raptors immediately bought out, further destroying their cap space), and two first round picks that turned out to be late first rounders, as a rejuvenated Carter helped the Nets reach the Conference Semifinals in 2006 and 2007. The Raptors soon after hired front office legend Wayne Embry to basically babysit Babcock before mercifully firing him a year later. Despite his disastrous time in Toronto, Babcock soon after was hired by the Timberwolves, serving as an assistant general manager and vice president for nearly a decade.

7) Dave Twardzik, Warriors (1995-1997)

As the starting point guard on the ’76-’77 Trail Blazers, Twardzik got a first hand education in successful roster building begetting championship success. Those lessons learned didn’t seem to carry over to his executive career, at least not during his brief time period with Golden State. If that tenure can be summed up in one quote, it would be Twardzik’s infamous pre-draft evaluation of Kobe Bryant: “he should go to college; he’s not ready.” This was his justification for instead using the #11 pick on Todd Fuller, who lasted two seasons with the Warriors, averaging 4.0 points and 3.4 rebounds per game. For the record, Peja Stojakovic, Steve Nash, Jermaine O’Neal, and Zydrunas Ilgauskas were also on the board. Lest you think this was an isolated incident, Twardzik had previously drafted Joe Smith #1 overall in 1995, passing on future All-Stars Rasheed Wallace, Kevin Garnett, and Jerry Stackhouse. This means the Warriors were one of two teams, along with the Clippers, that could have paired Kobe Bryant and Kevin Garnett on the same roster but deferred. But perhaps Twardzik’s most unforgivable move in the eyes of Warriors fans was his unceremonious trade of Tim Hardaway during the ’95-’96 season to the Heat for pennies on the dollar in Kevin Willis and Bimbo Coles. Following losing seasons in ’95-’96 and ’96-’97, Twardzik was fired and replaced by P.J. Carlesimo, who also took over as head coach.

8) Don DeJardin, 76ers (1970-1973)

No matter how directly responsible you are, when a team puts up the worst season in NBA history while you’re presiding as their general manager, then you’re making it on this list. DeJardin had a tough job when he took over as GM in 1970 for Sixers team that was effective but aging. But one has to set the bar for expectations higher than Philadelphia’s ’72-’73 season, when they lost a still NBA record 73 games. DeJardin was rightfully fired after that performance and replaced by Pat Williams, who quickly built the 76ers back into championship contenders. No one move by DeJardin stands out as particularly atrocious; it was more of a slow death by a thousand cuts. Of note: He traded away draft picks for four obviously washed veterans in Connie Dierking, Bob Rule, Mel Counts, and Bill Bridges, let coach Jack Ramsay walk for a job with the Braves, and used first round picks on middling talent in Dana Lewis and Freddie Boyd (to be fair, the 1971 and 1972 draft classes were notoriously weak in retrospect). All in all it’s far from the worst resume on this list but it’s enough to etch his name amongst the all-time not greats.

9) Vlade Divac, Kings (2015-2020)

When the Kings hired Divac as general manager in 2015, it seemed even at the time like a curious entreaty to the franchise’s seemingly long gone glory days. The move seems even more pandering and wistful in retrospect, after five years of incompetent decision making from the franchise legend. Divac was obviously in over his head from the beginning, admitting even years into the job that he still didn’t fully comprehend the salary cap system. Rather than taking the measured, meticulous approach regularly proven necessary to build small market franchises into contenders, he instead overpaid disinterested and/or washed up veterans like Rajon Rondo, George Hill, Caron Butler, Jordan Farmar, Ty Lawson, and Aron Afflalo, while alienating his young star DeMarcus Cousins, whom he was eventually forced to trade to the Pelicans for a so-so return. But the draft is where Divac truly did whatever is the opposite of shining, swinging and missing on Skal Labissiere, Georgios Pappagiannis, Justin Jackson, and Harry Giles, and worst of all, drafting Marvin Bagley over Luka Doncic and Trae Young in 2018. Recognizing how poorly things had, Divac stepped down as general manager immediately following the ’19-’20 season, which ended with the Kings finishing below .500 for the 15th consecutive year.

“On his way out the door, McHale managed to lob one final “fuck you” to Minnesota fans by getting only pennies on the dollar in exchange for Garnett from the Celtics.”

10) Bernie Bickerstaff, Bobcats (2004-2007)
11) Rod Higgins, Bobcats (2007-2011)

When the Bobcats started off as an expansion team in ’04-’05, Bickerstaff seemed like a safe bet as the team’s coach and general manager. He had over three decades of experience at that point, including a seven year stint as the lead executive for the Nuggets. But a closer review of his history reveals mixed results, at best, with personnel decisions in Denver and mediocre returns as a head coach beyond some initial success with the late ’80s Sonics. Perhaps that’s why Bickerstaff’s reign in Charlotte was marked by overstepping intervention from his bosses, first owner Robert L. Johnson and later president of basketball operations Michael Jordan. No matter whose fault it was, ultimately the roster decisions were disastrous, especially in the NBA Draft. Taking Emeka Okafor #2 overall in 2004 is somewhat defensible but reaching for local products Raymond Felton and Sean May in the 2005 lottery is not. That was all just stage setting for the disastrous selection of Adam Morrison #3 overall in 2006, a decision that arguably doomed the franchise. The man next put in charge of this ill-fated endeavor was Higgins, who took over as general manager during the 2007 offseason. Under his watch, the Bobcats did finally become a playoff team in ’09-’10, thanks in part to shrewd trades for Boris Diaw, Tyson Chandler, and Stephen Jackson. But the wheels fell off quickly from there, as Higgins and Jordan continued to waste Charlotte’s draft capital on low ceiling lottery picks like Tyrus Thomas, D.J. Augustin, and Gerald Henderson.

12) Wes Unseld, Bullets (1996-2003)

A true Bullets legend, Unseld won Rookie of the Year, MVP, and Finals MVP while spending his entire playing career with the franchise. After he retired, they basically handed him the keys to the franchise, first in a failed coaching endeavor from 1987 to 1994, then as general manager starting in 1996. Just as they did in his first year as coach, the Bullets reached the playoffs in his first year as GM. But in both cases, they also fell apart immediately due to poor leadership decisions. Unseld’s time making personnel determinations is marked by four times giving away young budding superstars for next to nothing. The first was trading Rasheed Wallace, just off his solid rookie season, for an aging Rod Strickland and an ancient Harvey Grant. Strickland’s presence helped Washington reach the 1997 playoffs but their future was being mortgaged. Unseld followed that up by trading Chris Webber, who was just entering his prime, to the Kings for declining former All-Stars Mitch Richmond and Otis Thorpe. Next up was diamond-in-the-rough Ben Wallace, whom Unseld sent off as part of a package to the Magic for the injury prone career back-up Ike Austin. Finally, after his new boss, Michael Jordan, decided to also make a comeback as a player, Unseld freed up the depth chart at shooting guard by short-sightedly trading Rip Hamilton to the Pistons for a package centered around Jerry Stackhouse. In retrospect, by giving away Hamilton and the two Wallaces, perhaps Unseld deserves a co-Executive of the Year designation with Joe Dumars for the ’03-’04 Pistons championship team? As it stands, Unseld presided over just two playoff appearances, both first round exits, in 13 years as coach and general manager. After he stepped down in 2003, the team almost immediately was rebuilt by his replacement, Ernie Grunfeld, who quickly added Gilbert Arenas and Antawn Jamison. 

13) John Weisbrod, Magic (2004-2005)

Just 35 years old at the time, with a background exclusively in hockey (first as a player and later as an executive), Weisbrod was a curious general manager hire for the Magic in 2004. His first major day at work was nonetheless inarguably successful, as he not only drafted Dwight Howard #1 overall, overruling factions within the organization that preferred Emeka Okafor, but also nabbed a steal with Jameer Nelson at the 20th pick. Then, less than a week later, Weisbrod made a move so controversial that he and his family had to flee their home due to death threats from Magic fans. Disgruntled reigning scoring champion and local hero (from nearby Auburndale) Tracy McGrady was traded to the Rockets for Steve Francis, Cuttino Mobley, and Kelvin Cato. There have certainly been worse trades in NBA history (many of which are detailed elsewhere on this list) but this one really touched a nerve for the Orlando fanbase that had previously been jilted by messy departures of Shaquille O’Neal and Penny Hardaway. Weisbrod soon after balanced one more good move (signing Hedo Turkoglu) with one more unfortunate one (trading Anderson Varejao and Drew Gooden for Tony Battie and two second round picks) and then stepped down as GM after just 14 months on the job, stating that it was not in the best interest of the Magic to have “a GM that would trade three NBA titles for one Stanley Cup.” Well, at least he was honest. Weisbrod did soon after return to his first love of hockey, first as a scout in the Stars and Bruins organizations and later as an executive for the Flames and Canucks.

14) Dan Issel, Nuggets (1998-2001)

In a story similar to Wes Unseld’s in Washington, Issel, a former Nuggets playing legend, struggled as the team’s coach for three years in the early ’90s but for some reason thought he’d have more success as their general manager. This was disproven almost immediately, with Issel’s first big move being a draft selection of Raef LaFrentz #3 overall, passing on Antawn Jamison, Vince Carter, Dirk Nowitzki, and Lafrentz’s college teammate, Paul Pierce. On that same day, Issel swung a trade with the Lakers for Nick Van Exel, a decision that would eventually come back to haunt him. When his first coaching hire, Mike D’Antoni wasn’t working out, Issel re-installed himself as head coach in an awe-inspiring measure of hubris. Just as had happened in his first coaching stint, it didn’t take long for the Nuggets players to turn on the surly and blame dodging Issel. In fact, they openly boycotted a practice, a revolt organized by Van Exel along with Issel free agent signee George McCloud. Despite this strife and the team’s continued struggles on the court (they finished below .500 for the sixth consecutive season in ’00-’01), Issel hung around as coach and GM for another year, finally getting mercifully fired for yelling a racial epithet at a fan. Before getting shown the door, he managed one last disastrous move, trading local legend and budding All-Star Chauncey Billups for three middling bench players.

15) Kevin McHale, Timberwolves (1995-2009)
16) David Kahn, Timberwolves (2009-2013)

What did Timberwolves fans ever do to deserve this? Sure, things weren’t always so bad under McHale, who was insightful enough to draft Kevin Garnett in 1995 and swing the trades for Sam Cassell and Latrell Sprewell that almost netted an NBA Finals appearance in ’03-’04. But he also committed one of the most ludicrous sins in general manager history, signing Joe Smith to an illicit under-the-table contract that, when discovered by the league, cost the franchise five first round picks, $3.5 million in fines, and multiple voided contracts. Two of those draft picks were later returned and McHale wasted them anyway, selecting Ndudi Ebi in 2003 and Rashad McCants in 2005. He also lavished oversized contracts on an assembly line of also-rans and chemistry poison like Marko Jaric, Eddie Griffin, Mark Blount, and Troy Hudson, while his draft day mistakes became a yearly tradition, from Rasho Nesterovic to William Avery to Randy Foye to Corey Brewer. On his way out the door, McHale managed to lob one final “fuck you” to Minnesota fans by getting only pennies on the dollar in exchange for Garnett from the Celtics. His replacement, Kahn, made his presence immediately known with one of the most chaotic draft strategies ever deployed, selecting three point guards in the first round in 2009 and somehow none of them were future All-Stars Stephen Curry, Jrue Holiday, or Jeff Teague. And yet, you could argue he performed even worse in the next two drafts, picking Wesley Johnson in 2010 over Paul George and DeMarcus Cousins, and then Derrick Williams in 2011 over Kawhi Leonard and Klay Thompson. Even though McHale was fired in 2009 and Kahn in 2013, Wolves fans continue to suffer due to their reigns, as the franchise has continually struggled to rebuild out of the mess they left.

17) Billy Knight, Hawks (2003-2008)

The summer of 2008 should have been a celebratory time for Knight, who had built the roster of a young, rising Hawks team that just snapped a seven year playoff drought. But instead, an exhausted Knight announced his resignation as the team’s general manager, citing his regular quarrels with ownership and blowback from fans still upset over his most debatable decisions. That’s because while the Hawks faithful recognized the team was rounding into a contender, they also knew that things could be even more aspirational if Knight hadn’t completely flubbed the 2004 and 2005 drafts. The latter was especially notable, as Knight selected Marvin Williams with the second pick despite Chris Paul and Deron Williams being on the board and Atlanta desperately in need of a starting point guard. Prior to that in 2004, Knight had made a savvy pick at #17 of Josh Smith but paired that with a reach for Josh Childress at #6 over the similarly skilled Andre Iguodala. He then made a poor decision with Shelden Williams at #5 in 2006, which has rendered itself more defensible over the years as that draft class panned out to be one of the weakest in the lottery era. At worst, Knight’s time in Atlanta was a mixed bag but those draft choices are dubious enough to merit inclusion on this list.

18) Jim Paxson, Cavaliers (1999-2005)

There was plenty of blame to go around when the Cavaliers failed to re-sign LeBron James in 2010. One of the more underrated anti-heroes of that story was Paxson, who drafted James and was fired years before talents were taken to South Beach, but laid down much of the groundwork that deterred the local legend from staying in Cleveland. To start with, it’s worth explaining how the Cavs landed that #1 pick in 2003 to start with and a large part of it was Paxson’s previous draft decisions, which included wasting lottery picks on Trajan Langdon, Chris Mihm, DeSagana Diop, and DaJuan Wagner. Paxson then spent the first two years of the James era constantly tinkering with the supporting cast, shuffling in and out middling, overpaid veteran talent like Kevin Ollie, Tony Battie, Jeff McInnis, Eric Snow, and Jiri Welsch (a player for whom Paxson gave up a first round pick and one year later he was out of the NBA). But Paxson’s piece de resistance came in 2004, when he let Carlos Boozer become a free agent on a handshake deal that he’d return, only to helplessly watch Boozer sign with the Jazz, leaving the Cavaliers with no compensation. Paxson was finally fired during the ’04-’05 season and replaced with Danny Ferry.

19) Isiah Thomas, Knicks (2003-2008)

Ever since his 1994 retirement as a player, Thomas has been a King Midas in reverse, turning everything he touches into shit. This includes his time as a real estate mogul, as part owner of the Raptors, as coach of the Pacers, as a popcorn magnate, as a television analyst, as owner of the CBA, and as coach at Florida International. But what people will remember most about his post-player career is his disastrous tenure as general manager of the Knicks. Just naming same of the players involved can induce PTSD in Knicks fans, whose franchise is just now getting over Thomas’ reign of terror and returning to playoff contention. Penny Hardaway. Stephon Marbury. Tim Thomas. Eddy Curry. Vin Baker. Jamal Crawford. Maurice Taylor. Quentin Richardson. Steve Francis. Jalen Rose. Zach Randolph. It was a murderer’s row of players that were either washed up, wildly overpaid, coach killers, disinterested in playing in New York, or all of the above. Not to mention massively overpaying role players like Jerome Williams while drafting incompatible talent like Renaldo Balkman and Wilson Chandler. Oh, and by the way, for the final two years of this roller coaster ride, Thomas also installed himself as head coach, with expectably disastrous results. If all that wasn’t enough, he also embroiled himself in near constant scandals, from sexual harassment allegations to salary cap shenanigans to supposedly imploring his players to commit hard fouls to instigate on-court fights. Thomas was finally released from his coaching and executive duties in 2008 but his damage to New York’s salary cap and reputation took years to unwind.