Orlando had led the Los Angeles Lakers by 12 at halftime and was on the verge of tying the best-of-seven series at two games apiece. Howard needed to make one of his two free throw attempts to make it a two-possession game. One of two and the Magic would have a chance to play a home game for a 3-2 series lead in Game 5.
He missed both. And seven seconds later Derek Fisher made the Magic pay, drilling a clutch 3-pointer to tie the score at 87 and send it to overtime, then sealing the 99-91 win that gave the Lakers a 3-1 series lead with another 3-pointer with 31.3 seconds to go in OT.
In all, Howard missed eight of his 14 free throws in Game 4. Afterward, he sounded somewhat dismissive of the issue, or very much like he does these days after games when he's asked about his still-abysmal free throw shooting as a member of the sputtering Lakers (So far this season, Howard is shooting a career-low .468 from the line and the Lakers are a disappointing 8-10).
"I just missed them," Howard said after that 2009 Finals loss. "I've been working on my free throws. They just weren't falling tonight."
It wasn't the first time a team had put Howard on the free throw line in crunch time and dared him to beat them. But it was definitely the most costly time. Not only did Orlando lose the series in the next game, it never even sniffed the Finals again over Howard's final two seasons with the Magic.
That game, those missed free throws at the end of Game 4, should have been Howard's lasting memory from his only trip to the Finals. The one thing he -- as a superstar in this league -- could work on in the offseasons to elevate his game, to make sure a meaningful game never again came down to the opposition knowing he couldn't deliver from the line in the biggest moments.
Instead, the problem has gotten worse. And if Howard can't make significant improvements at the free throw line, his new team will continue to be paralyzed by the problem at the end of games.
And forget Finals games.
Less than 20 games into the regular season we already are seeing opposing teams (no doubt eager to see the star-laden Lakers struggle through the frustrations and difficulties of not delivering on high expectations) willing to go "Hack-a-Howard" to win games against L.A.
In Tuesday's 107-105 loss to the Houston Rockets, the Lakers blew a 13-point lead over the final 10 minutes. Howard missed eight of his 16 free throw attempts, including five of 10 in the final 3½ minutes as the Rockets repeatedly put Howard on the line.
While Lakers coach Mike D'Antoni and Howard rightly argued after the game that it was the Lakers' breakdowns on defense that truly cost them, that shouldn't obscure the significant role Howard's free throw shooting played in the loss.
I'll let Rockets coach Kelvin Sampson explain:
"It gets the ball out of Kobe's hands. There's not a better fourth-quarter player in this league than Kobe," Sampson said after the game.
"They set the rhythm [in building a 13-point lead]. It was hard for us to get them out of that rhythm. They're such a rhythm team. It [Hack-a-Howard] comes under the category 'You do what you have to do to win the game.'"
It was the second straight game in which an opponent has exploited Howard's free throw shooting woes to beat the Lakers down the stretch. On Sunday, his old team, the Orlando Magic, used the strategy to rattle Howard (who was an ugly 9-for-21 from the line and 7-for-14 in the fourth quarter) and walk out of L.A. with a 113-103 win.
Tuesday's loss was the sixth time the Lakers have lost a game in which the number of their missed free throws exceeded the final margin of defeat.
According to ESPN Stats & Information, Howard has taken nearly half of the Lakers' free throws in crunch time situations (defined as the last five minutes of a fourth quarter or overtime when the score margin is five points or fewer) and has converted on only 44 percent of his attempts. The rest of the Lakers have combined to shoot 68 percent.
And the problem goes beyond crunch time. Howard has been fouled so much this season it has affected the Lakers' entire offensive flow, killing momentum and stifling pace.
How much more are teams fouling Howard than any other player in the league? Howard has taken 203 free throws. Kevin Durant has the second-most attempts at 165. How many more free throws has he missed than any other player in the league? He has missed 108. The Clippers' Blake Griffin is second, with 32 misses.
Howard's free throw shooting is a huge problem for the Lakers, no matter how much new coach Mike D'Antoni tries to take the pressure off his young center by saying he can live with it. Why has D'Antoni continued to express such unmitigated support for Howard in this? Why has he downplayed the problem? A better question may be whether he has the clout to do anything else. Remember: D'Antoni just got here. He's not in the same spot Phil Jackson was when he would selectively substitute Shaquille O'NealShaquille O'Neal in and out of games where opponents would egregiously foul him down the stretch -- think about the 2000 Western Conference finals against the Portland Trail Blazers, for example.
No, this is on Howard and Howard alone to address in much the same way O'Neal had to do throughout his career. It's Howard's battle to fight, his demon to wrestle. His time to put in, working on technique, over and over again. Dismissing the issue won't make it go away.
While O'Neal never conquered the problem, he never stopped trying, and he was able to battle it into submission often enough for the Lakers to win three NBA titles during his time in L.A.
According to ESPN Stats & Information, O'Neal made 52 percent of his free throws in crunch time situations during the playoffs. He battled it because it deeply bothered him. Because it embarrassed him and shook him enough that he recognized it was a problem, and that the Lakers couldn't win titles if he didn't get it together.
Perhaps the most telling series came in the 2000 Western Conference Finals when then-Portland coach Mike Dunleavy put O'Neal on the line a staggering 27 times in Game 1. It almost worked as O'Neal missed six in a row in the fourth quarter and seemed visibly shaken. But then he got it together and made six in a row to close out the 109-94 win. The Blazers continued to punish O'Neal and the Lakers with the tactic throughout the series and it worked. But when it mattered in Game 7, O'Neal came through, hitting 8 of 12 free throws, including two that tied the score at 77 with 2:44 to play.
"My father once told me that even if you shoot 99 percent and don't make the ones you're supposed to make, nothing else matters," O'Neal said after the win that sent the Lakers to the Finals against the Indiana Pacers.
At this point, any comparisons between Howard and O'Neal are probably unfair. Howard just got here, he should be allowed some time to adjust and settle in. But when you start a season with expectations as high as the Lakers did, then go 8-10 out of the gate, fair goes out the window.
In his short time with the Lakers, Howard has gamely played while still recovering from a back injury. He has played great defense, adjusted his role to two offenses that are different from anything he has ever done before, been a leader and had a good attitude.
All that should be celebrated, but unless he starts making the easy ones that matter most, and until the Lakers start winning like they should, as O'Neal's father said, nothing else matters.