A simple, 15 foot shot that is completely uncontested and worth a point to your team should be a “gimme.” Every player is capable of making it with a little bit of time and practice invested, yet a handful of points are routinely left on the board during the course of an NBA game. Most NBA players can cash in about 70% of their free throw attempts but there are always outliers at both ends of the spectrum. Steve Nash, Ray Allen and Reggie Miller are some notable names near the NBA top ten in all-time free throw, turning in nearly 90% of their career looks into a silky “swish.”

At the other end of the spectrum are the “brick layers,” “rim clankers” and “air ballers” who lack the proper mechanics, shooting touch and accuracy to put the ball in the basket from the charity stripe. These are the players who you don’t want at the line at the end of the game because of their perimeter shooting ineptitude. These are the players who were notorious for their poor free throw shooting and revolutionized the game, for one reason or another, which we will get into.

To qualify for the list, we took a few factors into consideration and note that no single one accounts for their place more than another.
  • Flawed shooting mechanics and lack of touch
  • Poor free throw percentage
  • Scope and volume of free throw misses throughout NBA career
Honorable Mention: Bo Outlaw, Kendrick Perkins, Adonal Foyle, DeSagna Diop, Bruce Bowen, Jahidi White, Brendan Haywood, Andrew Bogut, Bill Cartwright

Some poor free throw shooters to look out for in the near future: Kenneth Faried, John Henson

10. Chuck Hayes (60.3% Career FT, 0.5-0.9 FTA per game, 232-385 career FT)

Hayes is an undersized, gritty post player who channels hustle and toughness as well as any player in the league to be effective. He’s the only player on this list who hits better than 60% from his career, but is among the top NBA players all-time with the most grotesque stroke. He doesn’t have a fluid stroke, feet aren’t set or aligned with the basket, his elbow is way outside and across his head; it can even be used to draw in the opposition for lane violations. This is really the Charles Barkley golf swing of free throw shooting. Hayes has improved and smoothed his stroke drastically since he entered the league, but it will forever hold a place amongst the worst/funniest shot attempts in league history.

9. Kwame Brown (57.5% Career FT, 1.7-2.9 FTA per game, 976-1697 career FT)

Not sure that anyone is really surprised that he made this list given his track record in the league. Kwame has never had great shooting touch nor has ever been much of a face up threat as a post player, so it’s no surprise that his success from the line could be best described as “tepid.” He has a variety of highlight free throws in his career that span from banking one in to just completely air balling one. Air balling a free throw isn’t uncommon, it happens to even some of the best players in the league. The fact that these lowlights and poor shooting comes from one of the most scrutinized “busts” in NBA history sure doesn’t help Kwame’s perceived image.

8. Emeka Okafor (58.7% Career FT, 2.5-4.2 FTA per game, 1197-2038 career FT)

Since being in drafted in 2004, Okafor has been among the best in the league blocking shots and missing free throws. For his past seven NBA seasons, Emeka has routinely been at the bottom of the league in free throw percentage. He only slightly bends his legs, but his shot is mostly all arms which is why the majority of his attempts fall short and even provide us with a clip of the rare “double air ball.” There are other issues at play outside of mechanics, notably his touch and accuracy, but Okafor has been unable to put it together as a free throw shooter and likely never will.

7. Dwight Howard (59.8% Career FT, 5.4-9.1 FTA per game, 3085-5155 career FT)

Dwight is the premier center in the NBA and has developed into an offensive weapon during the past few years, even becoming a face up threat from the perimeter. Unfortunately, his free throw accuracy never quite caught up to his midrange game and he has struggled to break the 60% free throw conversion threshold since his rookie year.

He likes to take his time at the line, sometimes even too much, but one of the more noticeable problems in his technique is that he shoots predominantly outwards and not upwards like most players learn when they are young. However, he recently went out and hired a new free throw shooting coach to help turn around his fortunes from the line and that stroke is already looking better. In his young career though, Howard has left over 2000 points on the board just from free throw misses which equates to nearly 3.66 points per game.

6. Andris Biedrins (51.1% Career FT, 0.9-1.8 FTA per game, 377-738 career FT)

How the Internet is devoid of a rookie year Biedrins free throw attempt is beyond me, but Andris’ stroke entering the league was pretty horrendous and this clip really doesn’t do it justice. He has since taken the mechanical hitch but has stayed consistently bad for his career, if not gotten worse.

His free throw shooting was so bad that then Warriors head coach Don Nelson wanted Rick Berry to work with him and have Biedrins convert to the under-handed granny style that worked for Berry in his career. While the “ick” factor is largely gone from his free throws in his relatively short NBA career, Biedrins hasn’t figured it out and even posted a few seasons, although limited in game numbers, by shooting 30.6%, 32.3% and 16% from the line

5. Dennis Rodman (58.4% Career FT, 1.2-2.0 FTA per game, 1069-1832 career FT)

“The Worm” was an outstanding rebounder in his career, leading the league in boards grabbed in seven different seasons. Conversely, he was likely at the bottom of the league in free throw shooting just as much if not more during his career. In Detroit he made the effort to have some semblance of normalcy from the line but didn’t hold his follow through, took his eyes off the basket to watch the ball and didn’t square up his body to the basket. Alas his touch and mechanics just weren’t there and it quickly became apparent as his NBA career progressed.

In San Antonio he didn’t much make progress, becoming a little more nonchalant in his style and occasionally resorted to try something new. By the time he got to Chicago, his free throw became even more casual and less mechanical with a who am I kidding” type style where he was lucky to knock down a pair. Rodman was bad from the line but no one expected much from him there to begin with and he more than made up with it in his play in the post.

4. Shaquille O’Neal (52.7 % Career FT, 4.9-9.3 FTA per game, 5935-11252 career FT)

When you have a strategy based around sending you to the free throw line for your poor shooting percentage, then you belong on a list like this. The Hack a Shaq was an effective tactic to counteract O’Neal’s post dominance in his prime. While O’Neal has always been a poor free throw shooter who teetered around 50% for most of his career, he has always had a good sense of humor about it and even had the occasional “hot streak.”

Shaq never had great shooting rhythm, looked like was almost trying to balance it more in his hand and just didn’t ever have the shooting touch. How often do you remember Shaq in his prime hitting a face up 18-footer? His game was played with his back to the basket and unleashing that power in the paint, not finessing in shots from the perimeter. As such, if he would have hit just 70% of his free throws in his career than Shaq could have averaged 1.61 points per game more. Its baffling to think that Shaq missed over 5317 shots for his career.

At 7’1” with those oven mitts for hands relative to the actual ball, it’s about the equivalent of a normal person trying to shoot a tennis ball into a proportionately sized target the size of two tennis balls, which isn’t easy at all if you have ever tried, or ever just shot at a basketball hoop with one. Shaq’s career and free throws will forever be synonymous and he even acknowledged that he would miss them when he announced his retirement. Believe it or not, we might actually take him to make our free throws over a few people left on this list.

3. Chris Dudley (45.8% Career FT, 0.8-1.7 FTA per game, 691-1508 career FT)

Dudley was hustle guy in his career, nothing more and nothing less. The 6’11” Yale center was coveted for his size, toughness, rebounding ability and defensive play. Failing to mention free throws in that, Dudley was every bit as bad as you would expect him to be for someone with that description. Luckily for his teams, he didn’t get to the line much in career (only 1.7 times per game) and he is one of the few players who missed more free throws in his career than he made.

Dudley ran for Governor of Oregon last year and had a few political jabs based on his free throw struggles. He did set the NBA record for consecutive free throw misses at 13 and did miss 5 consecutive free throws on one opportunity for the Knicks after the opposing team committed an unprecedented 3 lane violations. However, he was routinely among the NBA’s best citizens, winning the 1996 award, and was always one of the bigger contributors in the community off the court.

2. Ben Wallace (41.5% Career FT, 1.1-2.6 FTA per game, 1093-2632 career FT)

Statistically, Wallace is historically the worst free throw shooter in the NBA and his career hasn’t finished. His career is chalked full of lowlights like that rare “double air ball”, uncanny fluke shots, opposing players high-fiving him for a make because of rarity, shots completely air balled completely offline, and perhaps rarest of all: making both. His shooting touch and accuracy were absolutely horrendous and his mechanics were subpar.

Nonetheless, Wallace was a rebounding and shot-blocking stud to be feared because of his tenacity, instincts and athleticism. The four time defensive player of the year has even sent away more shots than he’s made from the free throw line in his career. Wallace is the last guy you want at the line to win the game in NBA history, but luckily for him it has rarely come down to that.

1. Wilt Chamberlain (51.1% Career FT, 5.8-11.4 FTA per game, 6057-11862 career FT)

“The Stilt” holds a lot of records in NBA history that will probably never be broken, such as being the only center in history to lead the league in assists, averaging over 50 points for a season and scoring 100 points in a single game. However, 11862 times in his NBA career he was at the free throw line and 5805 he came away unsuccessful. For those doing the math, that’s a staggering 5.55 points per game that was left on the board for him and his teams. Imagine if he averaged closer to 35 points per game for his career as opposed to the 30.1 he ended his career with. That season he averaged over 50 points he got to the free throw line over 17 times per game, yet made only 10 of his attempts. If he shoots close to 70% mark for his career, then he averages nearly 2.15 points per game more.

While he wasn’t statistically the worse, the scope of how consistently bad he was from the line and the scope of how many points were left off makes him the worst in our opinion by comparison. How many times in those NBA Finals where his team came up short to Bill Russell and the Celtics would those few points from the FT line have been a game changer and tilted the odds in his favor? We can’t say for sure, but for as dominant as he was as a player it was only good enough to get him two titles compared to Russell’s eleven. He admitted that he was a head case when it came to free throws and the rules of the game were even changed by the game of tag with opponents intentionally fouling him to exhaustion throughout the game.

Watching old film of him shoot free throws (and unfortunately this is really all we have to go off of outside stats), it appears that he stands a couple feet behind the actual free throw line, shoots from one hand without his secondary to help balance, doesn’t extend his arm, doesn’t follow through, doesn’t square up and even though tis an all-star game, doesn’t appear to focus, let alone care. We can’t say that this is how Chamberlain shot through out his career and he did have some impressive free throw shooting performances and clutch makes, but the scope of how many points left off the board in his career is overwhelming.


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