1) Dominique Wilkins (Jazz, 1982)

Mired in mediocrity ever since their inaugural season in ’74-’75, the Jazz had a chance to make a quick turnaround when they landed the #3 pick in the 1982 NBA Draft. The draft class was top loaded with three surefire talents: North Carolina’s James Worthy, DePaul’s Terry Cummings, and Wilkins, from Georgia. There was only one problem. The Jazz’s best player at the time was Adrian Dantley and Wilkins, who was left at #3 after the Lakers took Worthy and the Clippers picked Cummings, played the same position as him. With no other viable options on the board, they took Wilkins anyway and spent the summer lobbying for him to switch positions to power forward. Though he was incredibly athletic and strong, Wilkins (who was 6’8″ and 215 pounds) rightfully knew that being battered as a power forward would run at variance with his smooth style and balked at the position change. Cash-strapped and holding a disgruntled draftee, the Jazz traded him to the Hawks for John Drew and Freeman Williams. It was one of the most disastrous transactions in NBA history, as Drew was decent but injury riddled in three years with the Jazz while Williams was washed up and soon after waived. Meanwhile, Wilkins became a nine-time All-Star in Atlanta but was also recently tempted to reflect on what might have been if he hung around in Utah and eventually teamed up with John Stockton (drafted in 1984) and Karl Malone (drafted in 1985). It’s also notable that the 1982 draft turned out to be far from a total bust for the Jazz, as they also landed two-time Defensive Player of the Year Mark Eaton in the fourth round.

2) Brian Shaw (Celtics, 1988)

This wasn’t an issue of roster fit or playing time, as Shaw quickly slotted in as a combo guard and heir apparent to Dennis Johnson. It also wasn’t concerns with the team’s management, as the Celtics were still an effective contender in the late stages of the Larry Bird era. Locale wasn’t a problem either, even though Shaw was a West Coast guy, playing his college ball at UC Santa Barbara. Instead, it came down to a lowball contract offer. He agreed to a one-year, $150,000 contract after the Celtics drafted him 24th overall in 1988 (this was long before the rookie scale regulations) but balked when they offered a similar deal after his strong first season. Instead of returning to the back court in Boston, Shaw absconded to Italy, signing a deal with Virtus Roma to be teammates with another player on this list, Danny Ferry. After a prolonged lawsuit, Shaw did eventually re-sign with the Celtics for five years and $6.2 million but was traded a year later to the Heat. Thereafter, he won three championships with the rival Lakers before closing out a 15-year career in 2003. 

3) Billy Owens (Kings, 1991)

In a classic “be careful what you wish for” scenario, Owens (rightfully) recognized an undesirable situation in Sacramento and forced his way into a seemingly glamorous but ultimately treacherous circumstance with Golden State. A lengthy, versatile small forward with preternatural skills, Owens showed flashes of being the next Scottie Pippen while at Syracuse and the Kings were happy to select him with the third overall pick in 1991. But Owens was less than pleased to be part of a franchise that was not only in one of the smallest markets in the league but in seemingly constant disarray. In the five years prior to ’91-’92, the Kings had swapped head coaches four times and lost 50+ games each season. When Owens refused to sign a contract, Sacramento actually swung an advantageous trade, dealing him to the Warriors for burgeoning superstar Mitch Richmond. Though Richmond was also displeased with his new locale, he eventually made six All-Star appearances as a King. Meanwhile, Owens found an icy reception in Oakland, where fans were vexed by the dissolution of “Run-TMC” and further discontented when their new acquisition failed to develop into an All-Star talent.

4) Steve Francis (Grizzlies, 1999)

By all accounts, Vancouver is a picturesque, diverse, cosmopolitan city with a bustling nightlife and culture. But most NBA players didn’t see it that way in the six years the Grizzlies were based in the Western Canadian locale. Or maybe they did but didn’t care because the U.S. to Canadian dollar exchange was a bigger factor. If you ask Francis, who was drafted second overall by the Grizzlies in 1999 despite his agent explicitly warning the team not to take him (he also reportedly purposefully tanked a pre-draft workout for the team’s front office), it was all of that and more. The NCAA star at Maryland also cited taxes, cold weather, the team’s poor performance (they had won just 23% of their games in the prior four seasons), the presence of a promising young point guard on the roster already (Mike Bibby, drafted the year before), the swirling rumors that they were about to move, and even that he and his entourage were supposedly hassled by security at the Vancouver airport. It’s no guarantee the Grizzlies would have been better off drafting Baron Davis, Lamar Odom, Shawn Marion, or Richard Hamilton but we know for sure that picking Francis was a mistake. He got his trade demand two months after the draft, getting dealt to the Rockets in a three-team, 11-player, three-draft pick blockbuster that also included the Magic.

5) Kiki Vandeweghe (Mavericks, 1980)

Anticipation was already high for the inaugural Mavericks season in ’80-’81 and peaked even further when they landed a steal at the #11 pick in the NBA Draft in Vandeweghe, a UCLA superstar with preternatural skills and a pro pedigree. The only problem is that their newly acquired rookie sensation had no interest in playing in the middle of the country, let alone for an expansion team. Instead, the younger Vandeweghe preferred to stay in California and play for the Lakers, Warriors, or Clippers, or suit up for the Knicks like his father, Ernie and uncle, Mel Hutchins did in the early days of the NBA. Dallas tried to convince him otherwise but when Vandeweghe held out of training camp, the preseason and the beginning of the regular season they finally obliged with a trade to the Nuggets in early December for a first round pick (which they used on future franchise legend Rolando Blackman). Denver wasn’t exactly New York or L.A., but Vandeweghe settled in happily, quickly becoming a two-time All-Star and one of the top pure scorers in the league in Doug Moe’s up-tempo offense. Mavericks fans were a little less pleased and for years would boo Vandeweghe whenever the Nuggets were in town, not just during pre-game introductions but whenever he touched the ball during the game. Despite the animosity at the time, Vandeweghe took his first front office job in the late ’90s with, you guessed it, the Mavericks, where he was instrumental in the development of fellow German big man Dirk Nowitzki.

6) Jon Barry (Celtics, 1992)

Considering their incredible championship success and their status as a keystone franchise of the NBA, you may be surprised to see the Celtics show up twice on this list. Besides Boston’s persistent notoriety as a racist fanbase (which alienated their all-time biggest star, Bill Russell, for many years after his retirement), the team also had a reputation in the ’80s and ’90s as stingy with contracts. As was the case with Brian Shaw above, such was the situation with Barry, whom the Celtics drafted #21 overall out of Georgia Tech in 1992. It wasn’t the money so much as the length of the contract that Boston offered to Barry, who wanted three years instead of the two on the table. Even before his holdout bled into the regular season, it was already a controversial draft pick in a fraught offseason for the team. With Larry Bird retiring, and Robert Parish and Kevin McHale aging fast, most fans were upset that the Celtics drafted a guard instead of some front court help. They eventually did trade Barry to the Bucks for a young power forward, Alaa Abdelnaby, who was solid but unspectacular and left in free agency just two years later. Barry didn’t have nearly the career of his father, Rick, or even his younger brother, Brent, but did spend 14 seasons in the NBA.

7) Danny Ferry (Clippers, 1989)

Playing professionally in Europe is a commonplace alternative now for anyone who feels scorned by the NBA but it was quite the novelty in 1989. But for Ferry, the #2 pick out of Duke, suiting up for Il Messagaro Roma in Italy’s Serie A beat playing for the Clippers team that drafted him. At least they were a contender in their respective league and didn’t have a similarly sized and skilled player like Danny Manning, whom Los Angeles had drafted #1 overall just one year prior. Ferry became just the second NBA draftee to spurn a rookie contract for a European one (Jose Ortiz did so in 1987 as well, though it was specifically to retain his Olympic eligibility for his native Puerto Rico) and the bold move was a throwback to the days when players could leverage ABA and NBA franchises against each other in contract negotiations. Left with few options, the Clippers traded Ferry’s rights with recent first round bust Reggie Williams to the Cavaliers in exchange for Ron Harper and two first round picks. Unsurprisingly for a trade involving these two star-crossed franchises, it arguably turned out poorly for everyone involved. Ferry never lived up to his #2 pick status or the massive $34 million contract the Cavs lavished on him, averaging just 7.8 points and 2.8 rebounds per game in 10 seasons in Cleveland, that included just three total playoff series wins. He did eventually win a championship as a role player on the ’02-’03 Spurs. Meanwhile, Harper had some good moments for the Clippers but mostly struggled with the effects of tearing his right knee.

8) Royce White (Rockets, 2012)

Athletes being forthcoming about their mental health struggles has become slowly normalized over the last few years, including NBA stars like Kevin Love and DeMar DeRozan. But things were different in 2012, when White was drafted #16 overall by the Rockets and became something of a sin-eater for pro athletes suffering from anxiety disorder. Despite his otherworldly athleticism and uniquely five-tool style of play, White’s openness about his anxiety was a red flag for many teams in the 2012 NBA Draft. He fell to the Rockets right outside the lottery and things started off strong, as he flew to Las Vegas to impress in summer league and attended rookie orientation. But right before training camp was scheduled to start, White began a holdout, demanding accommodations in his travel plans (he is deeply aerophobic) and the team updating its mental health policies. He eventually came to an agreement with Rockets management and played in 16 games for the Rio Grande Valley Vipers of the G-League but then abruptly shut that down, claiming it was detrimental to his mental health. The Rockets soon after traded him for a second round pick from the 76ers, who subsequently waived him before he could make his NBA debut. He finally did make three appearances with the Kings late in the ’13-’14 season, compiling just two personal fouls in nine total minutes of playing time. He’s since spent time playing professionally in the Canadian NBL and Ice Cube’s Big3.