Free throws are supposed to be easy. The foul shot exists as a near-automatic reward for drawing illegal contact from an opposing player, and most NBA players are able to make at least seven or eight out of every 10 free-throw attempts they are awarded. Players like Steve Nash, Steph Curry and Mark Price have been able to knock down 90 percent of the free throws they attempted during their careers, and Nash’s career percentage of 90.4 percent is currently the best in NBA history.
While there have been plenty of players who have taken full advantage of the free throw, there have been, of course, many who have been nothing short of atrocious from the charity stripe. Some players have been so bad that strategies have developed in which teams decide that they would rather put a poor free-throw shooter on the line rather than give the team an offensive possession outside of just late-game situations. The most prominent example is the famed “Hack-a-Shaq” routine, and even though Shaq has retired, the strategy lives on in the NBA today.
The players who appear on this list all had serious struggles from the free-throw line throughout their career. While it seems that free-throw shooting is a skill that can be worked on and improved, these players were unable to overcome their struggles at the line and could not take advantage of the freebies that were given to them. So while Chris Webber was able to vastly improve his free-throw skills over time, the players on this list came into the league shooting poorly from the foul line and left the league shooting poorly from the foul line.
*All stats are taken from Basketball-Reference.com and are correct as of April 1st, 2015.
15 Rajon Rondo
There are a lot of reasons that Rajon Rondo is considered enigmatic, and his free-throw shooting skills are certainly among those reasons. While this list is dominated by big men, Rondo appears on this list despite his relatively small stature (6’1”) and his status as a point guard. Rondo has been criticized in the past for being unwilling to attack the rim for fear of being fouled and put on the line, and his free-throw shooting has only gotten worse over the course of his career. So far this season, Rondo is shooting just over 36 percent despite a career average of over 60 percent.
14 Emeka Okafor
The former 2nd overall pick of the 2004 NBA Draft out of the University of Connecticut was definitely not chosen for his skills from the free-throw line. Okafor, a 6’10” power-forward who sometimes doubled as an undersized center during his time in the NBA, shot 2,303 free throws during his career but connected on just 1,344 while playing in Charlotte, New Orleans and Washington over nine seasons. That amounts to a percentage of 58.4 percent for his career, and his best season from the foul line came in his second year, when he shot 65.6 percent. He has never shot better than 60 percent since that season.
13 Elmore Smith
The 7’0” center went head-to-head with some of the NBA’s best big men, including Wilt Chamberlain and Bill Walton. While he battled the game’s greats on a regular basis, he faced a greater challenge when he toed the foul line. A 57.9 percent free-throw shooter, Smith had a season in which he shot a better percentage on contested shots from the floor (49.3 percent in 1974-75) than he did from the charity stripe (48.5 percent). His free-throw struggles did not prevent him from a successful career, however, as Smith led the league in blocked shots in each of the first two seasons the stat was officially recorded, once blocking 17 shots in a single game.
12 Dwight Howard
The Superman nickname isn’t the only thing that Howard apparently appropriated from Shaquille O’Neal when he entered the league in the 2004-05 season, as the Houston Rockets center is on Shaq’s level when it comes to free throws as well. Howard actually fared well during his rookie season by shooting 67.1 percent, but it has been all down hill in the years since. Howard has not eclipsed the 60 percent mark since his first season in the NBA, and his career mark is a paltry 57.3 percent. Like Shaq, Howard has become a late-game target as a result of his poor free-throw shooting abilities.
11 Kwame Brown
Kwame just can’t catch a break. He routinely appears atop compilations that include the biggest draft busts and worst top overall picks, and it could not have been easy being chosen by the player many consider to be the best to ever play the game in Michael Jordan. While Brown eventually carved out a niche in the NBA as a solid big man off the bench, the one thing he actually did well in his early years as a pro was shoot free throws. He shot over 66 percent in each of his first three seasons, but his ability apparently eroded thereafter to bring his career percentage down to 57 percent overall, including five seasons toward the end of his career in which he averaged under 45 percent from the line.
10 Dale Davis
The longtime Pacer struggled mightily from the line throughout his time in Indiana, including a season in which Davis recorded one of the worst single-season free-throw shooting performances ever. In 1996-97, Davis managed to make just 42.8 percent of his free throws, but this low point apparently sparked the power forward to improve his shooting from the line. Following that awful free-throw shooting season, Davis would average better than 60 percent in eight of the next 10 seasons, including one in which he averaged over 70 percent. Despite his late-career improvements, Davis still shot just 56.2 percent from the free-throw line during his career.
9 Bill Russell
Even the NBA’s greatest winner was not spared from free-throw line struggles. Russell, an 11-time NBA champion with the Boston Celtics, did have imperfections in an otherwise outstanding skill set. The 6’10” center who dominated basketball throughout the 1960s was not all that great from the free-throw line, which makes sense given the fact that Russell was more of a defensive-minded player. Owning a career mark from the free-throw line of 56.1 percent can be easily overlooked when you have more championship rings than any other NBA player in history.
8 Greg “Cadillac” Anderson
After a great run at the University of Houston playing alongside fellow members of “Phi Slama Jama,” Anderson entered the NBA in 1987 with the San Antonio Spurs. He bounced around the NBA quite a bit, playing for the Spurs, Bucks, Nets, Nuggets, Pistons and Hawks, never lasting more than two seasons at a time with any one team. Over the course of his 10-year NBA career, Anderson would shoot just 55.7 percent from the free-throw line, not far off his 49.4 percent career average on field goals.
7 Shaquille O’Neal
Shaq is one of the game’s greatest players, and he is also one of the only players to ever miss more than 5,000 free throws during the course of his career. It wasn’t for lack of effort, however, as many experts worked with Shaq throughout his career in an effort to rectify the one area of the game that made him quite vulnerable. Shaq had one season while in Los Angeles in which he averaged over 60 percent from the line (62.2 percent in 2002-03), but all of the effort never translated to anything at all in the way of results. The most dominant force in basketball was only able to register a career mark of 52.7 percent from the line, a fact that inspired the infamous "Hack-a-Shaq" strategy.
6 Bo Outlaw
Shortly after the departure of O'Neal from Orlando, the Magic replaced one of the worst free-throw shooters in the game with another terrible foul shooter in Bo Outlaw. A 6’8” forward who primarily focused on rebounding and defense, Outlaw shot 59.2 percent in his first season as a pro and shot 59.1 percent in his last season as a pro. The intervening years did not do much to help improve his overall percentage, which included two different seasons in which he shot less than 44 percent from the line. Outlaw had eight seasons in which his field-goal percentage was better than his free-throw percentage, earning him a place among the worst free-throw shooters in history.
5 Wilt Chamberlain
Like Shaq, Chamberlain holds the rare distinction of having missed over 5,000 free throws throughout his career. During his last nine seasons in the NBA, Chamberlain shot a better percentage from the floor than he did from the line, and he tried a number of different strategies to improve his free-throw shooting, although none ever worked better than the strategy he employed in which he leapt from behind the free throw line to put the ball in the basket at a much closer range. This led to a rule change stating that the player shooting the free throw has to remain behind the free-throw line until the ball has touched the rim. Over the course of his storied NBA career, Wilt managed to shoot just 51.1 percent from the line, including one season in which he shot an astoundingly awful 38 percent (1967-68).
4 Andris Biedrins
Biedrins was never really much of a standout player during his decade-long career in the NBA, but the 7-footer out of Latvia earned a place in the rotation for the Golden State Warriors for the better part of five seasons. During that time he struggled mightily from the free-throw line, including one season in which he missed 21 of his 25 free-throw attempts over the course of 33 games. During his 10 years in the NBA, Beidrins was able to make exactly half of his free throws, owning a career mark of 50 percent from the line.
3 Chris Dudley
Dudley was considered one of the most intelligent players in the NBA during his career, but despite having graduated from Yale University, Dudley was never quite able to figure it out from behind the free-throw line. The Conneticut native was able to have lengthy NBA career despite his free throw decencies, playing 16 seasons with the Cavaliers, Nets, Trail Blazers, Knicks and Suns. The power forward had four seasons in which he recorded a free-throw percentage below 40 percent, and his career average of 45.8 percent is one of the worst in the history of the NBA.
2 DeAndre Jordan
There are a lot of things DeAndre Jordan does exceptionally well in the NBA and there is good reason to believe that he could earn Defensive Player of the Year honors. As for his free-throw shooting, Jordan has been historically awful throughout his first seven seasons in the league. Shooting at a 41.6 percent clip for his career thus far is bad, and it appears that it is only getting worse. For the 2014-15 season, Jordan currently makes just 38.9 percent of his free throws, leading teams to employ the “Hack-a-Shaq” strategy when facing the Clippers. Perhaps one of the more interesting facts about Jordan is that he was once coached by an equally poor free-throw shooter in Kim Hughes, who shot just 39.7 percent during a 6-year pro career that included stops in both the ABA and NBA.
1 Ben Wallace
Ben Wallace was never granted a roster spot or playing time because of anything having to do with offense, as the longtime Pistons forward was one of the best defensive players to ever play the game. He won the Defensive Player of the Year Award four times, so the fact that he was terrible from the free-throw line was something the teams he played for were more than willing to overlook. Wallace’s career mark of 41.4 percent is just awful, and there were six seasons during his career in which his percentage was below the 40 percent mark.
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