Shooting a foul shot is supposed to be easy. NBA players possess varying skill sets, but they generally can knock down jumpers from all over the floor with defenders in their face; compared to that, taking an unguarded shot from a set distance should be called a cakewalk. They are called “free throws,” after all.

But, as longtime basketball fans will know, some of the game’s elite talents have struggled from the charity stripe. Whether it’s due to physical limitations, mental blocks, or any combination of factors, not everyone can convert that 15-foot shot.

With that in mind, let’s crack open the history books and consider the worst free-throw shooters in NBA history.

5. Shaquille O’Neal: 52.7%

If you watched basketball during the late 1990s and early 2000s, you’ll probably remember the “Hack-a-Shaq” strategy. At the time, Shaquille O’Neal was such a dominant player that him receiving the ball almost guaranteed two points. His Achilles Heel, however, was free throws, so opposing teams would intentionally foul him and send him to the charity stripe. There, things were less of a sure thing; the big man only converted 52.7% of his foul shots across his NBA career.

So, what was to blame for his poor shooting touch? A 2017 USA Today post explored that. While some have suggested bad form, the lingering effects of a broken wrist, or a lack of practice, the Big Aristotle had his own theory.

“The theory is, it was the man way upstairs’ way of keeping me humble,” Shaq explained. “Seriously. Because the way I played, the way I made everyone else around me better, all of the publicity I was doing — imagine if I was doing that and had shot 90% from the free throw line. I would have been arrogant. I’d probably be so arrogant. So it was just his way of saying, ‘Hey, buddy, you’re just like everybody else.’”

4. Wilt Chamberlain: 51.1%

On this date 61 years ago Wilt Chamberlain mysteriously shot 28-for-32 from the foul line. He tacked on 36 field goals (no such thing as a three for him) to give him an even 100. Pretty decent evening.

— Bob Ryan (@GlobeBobRyan) March 2, 2023

Going from one dominant big man to another, Wilt Chamberlain also struggled from the free-throw line. The center, for all of his physical gifts, only converted a shade over half of his foul shots during his time in the Association.

There was a notable exception to that reality: the 1961-62 season. During that campaign, Chamberlain sunk 61.3% of his attempts from the charity stripe; that might not sound like a world-beating number, but it’s a far cry from the 42.2% he posted toward the end of his career. What was the difference? Wilt shot underhand during that one (comparatively) successful season but eventually abandoned the technique.

It’s also worth noting that Chamberlain’s legendary 100-point game came during that campaign, and on that fateful night, he sunk 28-of-32 from the line. Without that accuracy, NBA history would look quite a bit different.

T-2. DeAndre Jordan: 47.5%

There was a time when DeAndre Jordan was famously bad from the free-throw line. During the early days of his NBA career, the big Texan shot less than 40% from the charity stripe. There were times — which, of course, are preserved on Youtube — when his attempts would completely miss the rim.

Over the years, though, things changed. As documented by Tim Cato in The Athletic, Jordan changed his footwork, mindset, and routine. He started to move with more confidence and reminded himself about dropping the ball into the basket rather than firing it at the rim.

And while those efforts may sound cliche, they paid off. Jordan is still one of the worst free-throw shooters in NBA history, but that’s largely based on his previous work. He’s still not a lethal marksman, but he’s now capable of breaking the 70% mark over the course of a season.

T-2. Andre Drummond: 47.5%

Andre Drummond is another player who improved from the line across his career. The UCONN product posted several seasons with a sub-.400 free-throw percentage during his early days in the Association, but has improved over the years. While you still wouldn’t want the center taking a crucial game’s dying seconds, he’s shot slightly about 50% from the charity stripe in recent seasons.

So what was responsible for that change? Matt Ellentuck broke things down for SBNation and suggested that the big man’s form evolved. While he previously relied on upper-body power, he started to incorporate more of a full-body movement, giving him a softer touch.

Whatever happened behind the scenes, the days of missing 23 free throws in a game seem to be long gone.

1. Ben Wallace: 41.4%

Ben Wallace was elite when it came to certain parts of his game. The Alabama native didn’t play at a big-time college and went undrafted but worked his way into the Association. And he wasn’t just a benchwarmer, either; during his time with the Detroit Pistons, Big Ben stood tall as one of basketball’s best defenders and rebounders.

But when it came to the other end of the floor, it was a different story. Wallace only averaged 5.7 points per game across his career, and his foul shooting didn’t help matters. He only made 41.4% of attempts from the charity stripe; his career high-water mark was 49% during the 2003-04 season.

Big Ben, however, wasn’t there to score points, and his overall impact more than made up for some ugly foul shots.