On March 3, with the Boston Celtics trailing the Houston Rockets 120-117 with 5.2 seconds remaining, Irving went to the line. After calmly nailing the first free throw, he attempted to miss the second off the back of the rim to give his team a chance for a putback to tie the game.
Instead, Irving banked it in, bringing the Celtics within one and giving the ball to the Rockets.
After an intentional foul gave Houston guard Chris Paul two free throws, Irving went back to the line with 2.8 seconds left and Boston once again trailing by three. The guard made the first and attempted to miss the second. This time, the ball ricocheted off the backboard without touching the rim, giving the ball back to Houston and effectively ending the Celtics' chances at tying the game.
Throughout his career, Irving has built a reputation as a clutch performer. Against the Rockets, his inability to miss cost his team.
"I suck at [missing free throws]," Irving told reporters that day. "I've been up there probably four, five times and I've failed every single time trying to miss on purpose. I don't know. Don't ask me. I keep telling my teammates I'm not good at missing. I'm not. I'm serious."
Irving isn't alone. Even the league's best foul shooters admit missing on purpose is more difficult than it looks.
"You're trained all your life to make free throws," said Los Angeles Clippers guard Lou Williams, who shot 86.2 percent from the line in clutch situations this season, per NBA.com. "So you have that rare scenario where somebody asks you to miss one, and it's extremely difficult."
It isn't enough to simply miss the free throw. It has to hit the rim, or it's a violation. This allows for a few options, none of which are foolproof, even for the world's best shooters.
The strategy rarely works, but the Oklahoma City Thunder executed it to perfection April 23, 2017, late in Game 4 of last year's first-round series against the Houston Rockets. With 21.7 seconds remaining and Steven Adams at the stripe, Russell Westbrook positioned himself beyond the three-point line. Adams drained the first free throw before hitting front rim on the second, grabbing the rebound and kicking the ball out to Westbrook, who drained a three to cut Houston's lead to one.
Oklahoma City ultimately lost, but Adams put it in position to come back by expertly missing from the line.
Cleveland Cavaliers guard Jose Calderon holds the NBA record for free-throw percentage over a full campaign, shooting 98.1 percent in the 2008-09 season with the Toronto Raptors. During his 13-year career, Calderon has maintained an 87.3 percent success rate from the charity stripe, yet he isn't sure he could miss in that situation.
"You've got to think about it," Calderon told Bleacher Report in March. "Instead of looking to the center, you might have to look to the side of the rim and try to hit the side. If you go short, it could be an air ball."
Shooters can aim for the front of the rim, which carries the risk of coming up short and earning a spot on Shaqtin' a Fool for air-balling a free throw. Aiming for the back iron opens the possibility of overshooting and banking it in, as Irving did against the Rockets. The other option is to shoot for one of the rim's sides, and even then, you have to make sure one of your bigs is strategically positioned to take advantage.
"It becomes a big scrum," said former New York Knicks coach Jeff Hornacek, who shot 87.7 percent from the line in his 14-year playing career. "Guys crash in there, and what you're really doing is trying to bounce it up there so somebody has some chance to go to the side. If you aim for the side of the rim, it's a chase-down. It's kind of pure luck, how it bounced off there and if your big can corral it and tip it, and if you've got a guy strong enough to knock guys around and clear some space."
There isn't much room for error. The shooter has to get the angle exactly right for the ball to hit the rim and bounce to a teammate, not an opponent. There's no precise science to it, and the situation occurs too infrequently for teams to spend much time working on it in practice. But it's a legitimate strategic move, and players have to be prepared on the off chance the need to miss does come up.
"Most teams have a play where you miss it and you try to maneuver a guy to a certain spot," Rockets coach Mike D'Antoni told B/R. "And if you hit that spot, whatever spot it is, and you work with him. Some guys try to shoot it quick, so you can get in the lane quicker."
The great shooters get thousands of practice reps every day. They spend years refining their form and mechanics, and shooting a free throw comes down to muscle memory for many of them. When they have to miss, it can get in their head. It's a deviation from the routine they spend their entire careers building.
"It's not easy," said Calderon. "You really have to concentrate. That shot is so automatic. You don't think about it because it's always the same. I think you've just got to think and look for the side of the rim or somewhere else. It's not as easy as it seems."
Paul tied with Denver's Jamal Murray as the NBA's best clutch foul shooters with a minimum of 20 attempts, shooting 96.3 percent with their teams within five points in the final five minutes of a game, per NBA.com. Even Paul admits intentionally missing a free throw is more difficult than it looks, although he isn't as down on his ability to miss as Irving is.
"It's tough," Paul told B/R. "That's a skill. Some people try to hit the front of the rim. It's risky to try to hit the backboard because you might miss the rim."
Not that the Rockets have been in that position much this season. They outscored opponents by 8.5 points per game, easily the highest differential in the NBA. They're on the verge of advancing to the second round of the playoffs with a 3-1 lead over the Minnesota Timberwolves, coming off a commanding 19-point victory in Game 4 of that series on Monday.
But their competition will get tougher the deeper they get into the playoffs, with a potential meeting with the Golden State Warriors if they reach the Western Conference Finals. Those games could and likely will be closer, and Paul is confident that if he has to miss a free throw, he'd be up to the job.
"I bowl a lot," Paul laughs. "I'd like to think my accuracy is good."