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#3 Dwight Howard
Dwight Howard was a dominant big man during his best days in the NBA. Regardless of what his current status in the league is, Howard is surely a future Hall-of-Famer whose accolades deserve more credit than he often gets, although he could be described as an underachiever.
Still, Howard is an eight-time All-Star, eight-time All-NBA and five-time All-Defensive player. He also won three Defensive Player of the Year awards with the Orlando Magic and even dragged the team to the 2009 NBA Finals.
Howard won an NBA championship as a role player for the 2019-20 LA Lakers and is back in LA looking for a second ring and, finally, a championship parade in LA. Among his lowlights, free-throw shooting will always be among the biggest ones, as he made 56% of his free throws so far.
Howard has missed the third-most free throws in NBA history, with 4,044 out of 9,309 attempts. He's attempted the seventh-most free throws in league history, but ranks 32nd in makes.
#2 Shaquille O'Neal
Another big man with an illustrious NBA career, but one that could not see the free-throw line. Shaquille O'Neal has a case to be the most dominant NBA player of all time, as he simply could not be stopped during his greatest days.
O'Neal's dominance led the LA Lakers to three consecutive NBA championships between 2000 and 2002 and earned him three straight Finals MVP awards too. Shaq also added a fourth NBA title to his resume with the Miami Heat in 2006, when he was still dominant.
He ended his career with 15 All-Star appearances, 14 All-NBA and three All-Defensive selections, four titles, three All-Star MVPs, a regular-season MVP, two scoring titles and more.
But nobody would ever call O'Neal a great free-throw shooter. The big man probably didn't need to be a great one though, but he missed 5,317 free throws in his illustrious NBA journey.
His free-throw shooting percentage of 52.7% is the fifth-worst in NBA history among players with 1,200 misses or more.
#1 Wilt Chamberlain
Wilt Chamberlain, like the 'Diesel' O'Neal, was an extremely dominant center in his basketball career. Chamberlain's name is often #1 on many scoring lists, especially when you consider his record-setting 1961-62 NBA season, when he averaged 50.4 points per game throughout the season.
Of course, his 100-point game against the New York Knicks on March 2nd, 1962 will always be remembered and probably never surpassed by another player. Chamberlain retired with two NBA titles and seven scoring titles in his career.
He also has the second-best career average of points per game in NBA history, at 30 per game. However, Chamberlain was a bad free-throw shooter. Like O'Neal, he probably did not need to master that skill, but the numbers are simply bad.
The four-time MVP (including one MVP as a rookie) missed 5,805 of his 11,862 career free-throw attempts. He made only 51% of his free throws in his career (the number went down to 46% in the NBA Playoffs) and owns the fourth-worst FT percentage among players with at least 1,200 misses.
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