Every franchise in the league occasionally drafts a player that doesn't quite live up to his expectations. There's just no escaping from it. Not even for San Antonio.
This is five picks that might have struck those kind of thoughts into Cleveland brains.
Have a look at our earlier posts in this series while you're at it!
- 5 Blazers that could have been
- 5 Bulls that could have been
Picked 1st overall in the 2013 NBA Draft by Cleveland Cavaliers.
Anthony Bennett is by many viewed as one of the biggest draft busts in league history.
While that might be an overstatement since it generally was a pretty shitty draft back in 2013, lots of players from that draft still performed better than Bennett, and he's certainly one of the worst players to have been selected with the 1st overall pick.
When Bennett was picked in front of players like Victor Oladipo, Otto Porter, Nerlens Noel, C.J. McCollum, Michael Carter-Williams, Kelly Olynyk and Giannis Antetokounmpo he became the first Canadian in league history to be selected with the 1st pick in the NBA draft.
Even though ESPN ranked him #1 among all forwards in the high school class of 2012 and he was selected as the MWC Freshman of the Year in his only college season, this pick still received a lot of criticism from NBA analysts as many of the players named above showed more potential.
Well, something something Cleveland sports management...
After 52 games and a historically bad rookie campaign for a 1st overall pick, Anthony was traded to Minnesota Timberwolves in a three-team trade including the Philadelphia 76ers.
In Minnesota Bennett improved marginally, but in February, 2015, he sustained a shoulder injury and was sidelined for most of remaining season games.
On September 23, 2015, after only playing 57 games in Minnesota, Bennett was waived via a contract buyout. A week later he signed a one-year contract with Toronto Raptors where he had such a bad start that Bennett himself asked to be sent down to Toronto 905, the Raptors D-League affiliate.
What's notable about it is that Bennett by doing so added another trophy to go along with his first Canadian to be selected with the first pick-one, when he then became the first and only first overall pick to play in the NBA D-League!
As the Raptors was frustrated with Bennett and his work ethic they chose not to resign him, and on July 10 Bennett signed a contract with the Brooklyn Nets.
During his first three seasons, Bennet played 128 games averaging 4.2 points, 3.1 rebounds, 0.5 assists, 0.4 steals and 0.2 blocks while shooting .388 from the field, .256 from three and .657 from the line in 12.8 minutes per game.
He's still only 23 years old and has a lot of time to develop, but it seems quite likely that he will never live up to the expectations of a number one pick.
Picked 10th overall in the 2004 NBA Draft by Cleveland Cavaliers.
Playing for Creswell High School in Oregon, Luke Jackson was soon discovered for his basketball talent and was named Oregon's Class AAA Basketball Player of the Year both in 1998 and in 2000.
Even though Jackson was a 6-7' small forward he played his game like a guard and averaged 24.2 points, 8.1 assists and an impressive 5.0 steals per game in his senior year at Creswell.
His success continued at the University of Oregon, and on February 17, 2001, in a game against Washington Huskies, he became only the second freshman in Pac-10 history to get a triple-double.
Jackson stayed at the University of Oregon for four years was selected to the All Pac-10 first team in 2003 and 2004, was a consensus second-team All-American in 2004 and got All-American honors from ESPN, CBS, The Sporting News and many other media networks.
In Pac-10 history, Jackson is the second player to total more than 1,900 points, 700 rebounds and 400 assists over his career.
As the Cavaliers at the time needed shooters they decided to pick the sharp shooting Jackson over players like Al Jefferson, J.R. Smith, Jameer Nelson, Tony Allen, Kevin Martin and Josh Smith (hehe).
Wrong choice! On his very first NBA day he herniated two discs in his back, and his tenure in Cleveland ended on October 27, 2006, when he was waived after only have appeared in 46 games in two seasons.
He then bounced around between D-League teams and 10-day contracts in the NBA, playing another 27 regular season games before going to Europe to end his career in Israel.
During four seasons in the league Jackson played 73 games, averaging 3.5 points, 1.2 rebounds, 0.8 assists and 0.3 steals pere game while shooting .357 in field goal percentage.
As of right now Jackson serves as the head coach of the Northwest Christian University, in Eugene, Oregon.
Picked 35th overall in the 2002 NBA Draft by Cleveland Cavaliers.
Don't get me wrong, Carlos Boozer became a really good player and considering the fact that he was picked so late he was probably the steal of the 2002 NBA draft.
But it's what could have been between him and Cleveland that makes him qualify for this list.
Before his NBA career could start Boozer grew up in Alaska, where he led the Juneau-Douglas Crimson Bears to back-to-back state championships before electing to play for Duke University.
Even though he had a successful career at Duke many teams believed Carlos to be an undersized center, and not mobile enough to transform into a power forward.
Those teams we're wrong, and Boozer finished his rookie campaign averaging 10.0 points and 7.5 rebounds per game while shooting 0.536 from the field. Good enough for a NBA All-Rookie Second Team selection.
In his second season with the Cavaliers he already averaged 15.5 points and 11.4 rebounds per game, so the Cavaliers front office wanted to award him for his strong play and worked out a deal with Boozer's agent to get him out of his second round contract, so that they could resign him on a much larger contract and compensate for his low pay the previous seasons.
Shouldn't have done that... Boozer went on to sign a bigger contract with Utah Jazz, where he became a vital scorer and rebounder while also gaining two All-Star nods and a All-NBA Third Team selection in 2008.
You can only wonder what could have been in Cleveland if LeBron had a prime Carlos Boozer as offensive help in their 2006 - 2007 playoff run. You think they could have gotten the title?
Boozer is currently trying to get back into the league after a year off, but at his age it's not that certain that he'll ever get another NBA contract.
If he doesn't he'll end his 13 season career averaging 16.2 points, 9.5 rebounds, 2.2 assists, 0.9 steals and 0.4 blocks while shooting .521 from the floor in 31.2 minutes per game.
Picked 6th overall in the 2002 NBA Draft by Cleveland Cavaliers.
Point guard prodigy Dajuan Wagner is possibly the best high school player in New Jersey history.
Playing for Camden High School he became the 23rd player in American High School history to score at least 100 points in a single game, and averaged 42.5 points in his senior year.
During his High School tenure Wagner scored 3,462 points to set the record for most points ever in New Jersey High School history while also being selected as the Naismith Prep Player of the Year in 2001.
After playing one season for the University of Memphis, head coach John Calipari ripped up Wagner's scholarship papers in front of him, to force Wagner (projected as a lottery pick) to leave and not miss out on a NBA paycheck.
After being picked by Cleveland Cavaliers in the same draft class as Carlos Boozer, Wagner sadly had to miss some time in his rookie season to attend the trials of his step father, Camden drug kingpin Leonard "Pooh" Paulk. In 47 games Wagner still averaged 13.4 points and 2.8 assists per game.
After that everything went downhill as Wagner was bothered by injuries the next two seasons while also being hospitalized with inflammatory bowel disease, which more or less put him out of the league.
In three seasons Wagner played 102 games for the Cavaliers, averaging 9.4 points, 1.4 rebounds, 1.9 assists and 0.7 steals in 21.5 minutes per game.
Picked 11th overall in the 1999 NBA Draft by Cleveland Cavaliers.
Trajan "The Alaskan Assassin" Langdon, point guard and another Alaskan basketball prospect.
Langdon managed to become a deadly shooter even though he grew up in Anchorage, where he was forced to hoop in gloves and snow boots.
In High School Langdon led his East Anchorage to the 1994 Alaskan State Championship title, and was a 3-Time Alaskan Player of the Year.
He later went on to play college ball for Duke University where he led the Blue Devils to the 1999 NCAA championship game and set a school record for most career 3-point field goals made.
When Langdon suited up in the Cavs jersey for the 1999 - 2000 season he became the first Alaskan player ever to play in the NBA, but due to an arthroscopic surgery on his right knee he only managed to play 10 games in his rookie season.
He then played two more seasons in Cleveland with limited playing time.
While he improved some it was not enough to draw the interest of Cleveland to resign him and he therefore moved to Europe to play in the Euroleague.
Langdon had great success in Europe where he became one of the best players and Euroleague champion with CSKA Moscow in 2006 and 2008 while also winning the 2008 Euroleague Final Four MVP award.
He was also selected for the All-Euroleague Second Team in 2006, the All-Euroleague First Team in 2007 & 2008 and the Euroleague 2001 - 2010 All-Decade Team.
Too bad for Cleveland that he never got to utilize his skills in the Quicken Loans Arena, as he only got to play 119 games for the Cavs.
In those games he averaged 5.4 points, 1.3 rebounds, 1.3 assists and 0.5 steals in 14.6 minutes per game while shooting 0.396 from the three point line.