Bob Ryan is one of the greatest NBA journalists ever. He covered the NBA from the 60s onwards and is one of those guys who remember almost every boxscore ever. Ryan is one of the few people who don't suffer from the fact there's not a lot of video of Bill Russell, Wilt Chamberlain, Oscar Robertson, and other great players from that era. He saw them all.
One of his favorite games featured none other than The Big Dipper. Ryan went to a doubleheader in the Boston Garden for the price of $2 (!) and witnessed Wilt post one of the craziest boxscores in NBA history.
“One of my favorite stories, I was witness to a record that is yet to be broken, and I doubt ever will be broken. I saw Wilt Chamberlain on a night in which he scored 52 points, set an NBA record by missing 28 free throws. He was 8 for 30.”
Bob Ryan, The BS Podcast
Yes, I know the level of competition and athleticism in the game was different back then. So was the pace. There were a lot more opportunities to score and grab rebounds and all that. But still, if you look at all the great high scoring games, a lot of free throws are involved. It stops the clock, and usually, guys who post huge numbers shoot from the charity stripe at a very high rate.
This is the complete opposite. Chamberlain probably would've scored more if they didn't foul him as much. It is also a reminder that Wilt's best free-throw shooting season was when he shot underhand but reverted to the overhand because the underhand wasn't cool enough.
Bob Ryan said he is convinced the record of 22 missed free throws will never be broken. He is wrong - it already happened. On January 21st, 2016, Andre Drummond missed 23 free throws, setting a new infamous record level.
But unlike Wilt, he didn't have a monster game that night. Drummond went 13 of 36 and finished the game with 17 points.