A career 52.5 percent free-throw shooter, Shaq is up to a less gruesome 58.7 percent this season. Nathaniel S. Butler/Getty Images Clang! Doink! Boing! Rat-a-tat-tat! It's been an amazing career for Shaquille O'Neal in most respects, but hanging over it is the specter of his greatest weakness -- free-throw shooting. The Big Brick has made only 52.5 percent of his career attempts, the second-worst percentage among those who have attempted 5,000 free throws or more, and rivaling Wilt Chamberlain (51.1 percent) for the cellar. Oddly, he has become worse with age, missing more than half his shots for five straight seasons before squeaking by at 51.3 percent a season ago. Shaq's tragic flaw will loom a little larger in the coming days, because he's closing in on an amazing milestone. With eight more misses, he'll become just the second player in history to miss 5,000 free throws; at his 2008-09 rate of 2.7 misses per game he'll hit the mark in his next three games -- perhaps even on Christmas Day against San Antonio and coach Gregg Popovich, who has a penchant for the Hack-a-Shaq strategy. Only Wilt Chamberlain has bricked more, and he played in the turbo-charged '60s when the pace was much, much faster than it is today (see chart). Mind you, this only includes regular-season games. In the playoffs, Shaq has bricked another 1,131 free throws, more than doubling every other player in history except Chamberlain. Despite his claim that he makes them when they count, he's actually significantly worse in the postseason (50.1 percent) than the regular season (58.1 percent) -- the low point came when he helped Miami to its only title despite shooting 37.4 percent during the playoffs. To put 5,000 missed foul shots in perspective, consider that it's nearly 50 percent more than any other player in history save for Chamberlain. The next player on the list, Karl Malone, went to the line more often than any other player in history but is 1,591 misses behind Shaq; to miss 5,000, he would have had to shoot 62.1 percent instead of his 74.2 percent career mark. Or consider that Shaq has missed more free throws than Hall of Fame center Bob Lanier attempted, and also is closing in on inductees Bob McAdoo, Nate Thurmond, Bill Russell and Robert Parish. With reasonable health, he'll catch all of them by the time his contract expires at the end of next season. So in tribute to Shaq's 5K milestone, and with a big assist from the ESPN Research team, let's tackle our own big 5 -- the five biggest questions on Shaq's free throws: 1. Anyone else who might miss 5,000? To hit 5,000 requires a confluence of two skills at historic levels -- the ability to get to the line, and the inability to convert once there. A player needs to miss more than 300 free throws a season to get there within the time frame of a reasonably long NBA career; that, in turn, requires him to get to the line at least eight times a game, since even the worst foul shooters in history make about half their attempts. Eight attempts per game is an amazingly high standard -- only nine players average that many this season, and they would have to keep it up for another 15 years or so before they would have enough attempts to rival Shaq. Nonetheless, at least two players have enough going their way in terms of attempts, misses and youth that they could plausibly catch Shaq in free-throw misses. The first is an obvious one: Dwight Howard. The imposing Orlando center has already misfired 1,142 times, and at just 23 he has plenty of time left to get the remainder. He's making up ground fast, too, by missing 5.0 free throws per game this year. At that rate, he'll shatter Shaq's mark, not to mention Chamberlain's. Howard would hit the 5,000 plateau by the time he was 32, and presumably have several years of wayward shooting left to pursue greater heights. Of course, the key phrase is "at that rate." Howard needs to continue both drawing foul shots and missing them at a prodigious rate in order to move up the charts. It's possible, especially considering that his free-throw-attempt rate has gone up every year while his marksmanship has stayed in the high 50s, but if Howard pulls a Malone and gets better from the stripe with age, he'll fall well short. Howard's example makes it seem easy, but to show how hard it would be to get to 5,000 misses for most players, consider LeBron James. He gets to the line more than almost anybody else, averaging more than 10 foul shots a game last season, and is one of the game's least accurate stars at 73.3 percent for his career; additionally, he started playing at 18 and has time on his side in a major way in terms of pursuing career records. Even so, at his rate of the past two seasons, James wouldn't clear the 5,000-miss mark until he was 42 years old. And if his early-season improvement to 79.6 percent from the line this year holds up, you can kiss even those slim odds goodbye. 2. All-time team of players with fewer than 5,000 FTAs? The example above dovetails into another discussion of what an amazing feat it is to miss 5,000 foul shots -- namely, that most players don't even attempt 5,000, much less brick that many. Combining NBA and ABA history, only 68 players have attempted 5,000 free throws. Dikembe Mutombo, for instance, has played 17 years and is still 49 short. While several active players will add to that list in due time -- such as Howard and James above -- you can make a pretty awesome All-Star team just from the players with fewer free-throw attempts than Shaq has missed. In fact, let's do that: Point guard: Anybody from Phoenix. That list includes two-time MVP Steve Nash (2,488 attempts; at 34, in no danger of reaching 5,000), fast-break phenom Jason Kidd (3,621 and adding slowly) and penetrator extraordinaire Kevin Johnson (4,691). (Side note: Do you realize that if you live in Sacramento right now your government chain of command is Kevin Johnson-Arnold Schwarzenegger? Is that just a little surreal?) Of course, taking the Phoenix trio means that we must exclude the all-Knicks backcourt of Walt Frazier (4,226) and Earl Monroe (4,513), not to mention the incomparable Gary Payton (4,480). That list already gives us at least five point guards who are either in the Hall of Fame or will be there soon, and we're barely scratching the surface of candidates for this "honor." Shooting guard: Scottie Pippen. Pip didn't see much time at this position during his heyday because the Bulls already had a pretty fair shooting guard, but since my team is already stacked at small forward (as you'll see in a minute), I have the luxury of moving the versatile Pippen to the 2. The greatest second banana in league history had 4,437 trips to the stripe, even after a decade and a half as one of the game's premier slashers. But if you'd rather have the best player from a team that won it all at this position, we can always throw a little love to forlorn Seattle in the form of Dennis Johnson (4,754). Or we can go the other way and throw in a great scorer like Pistol Pete Maravich (4,344), or throw a bone to the old-timers with "50 Greatest" selection Bill Sharman from the old Celtics (3,559) or 1958 scoring champ George Yardley (3,434). Yet this is one of the weak spots in the lineup -- it's one of the two spots where we don't have a multiple MVP winner taking the floor. Small forward: Larry Bird. A three-time MVP and, obviously, one of the greatest players of all time, Bird nonetheless attempted only 4,471 free throws in his career. Actually, we have four of the top seven players in the 1984 scoring race represented here -- fellow Eastern Conference executive Kiki Vandeweghe finished his career with 3,997 tries, while Bernard King (3,972) and Mark Aguirre (4,944) also fell short. Between them, those four had seven top-three seasons in the scoring race and 15 seasons averaging 25 points or more but none of them topped 5,000 free-throw attempts, and only Aguirre came very close. Power forward: Kevin McHale. Before he was in charge of ruining the Wolves, McHale was the league's most feared 4 in the low post. But all those corkscrewing up-and-unders still produced only 4,554 free-throw attempts, a meager total next to Shaq's mighty sum. Moving out on the court, the best high-post player of his era, Chris Webber, didn't get there either (3,906), nor did gritty Hall of Famer Dave DeBusschere (3,730) and high-flying inductee James Worthy (3,184). Center: George Mikan. That's right -- Shaq's 5,000 free-throw-miss feat is so rare that even the Shaq of his era, Mikan, couldn't get to the line for 5,000 attempts, much less miss that many. The original Lakers center finished with 3,924. If you'd like to put an asterisk next to that number, given how Mikan beat a hasty retreat into retirement at age 30, we'll just have to make do with another all-time great. Like, say, Willis Reed. The two-time Finals MVP and one-time regular-season winner retired early, yes, but with just 3,298 free-throw attempts, he wasn't a threat to hit the 5,000 mark anyway. Over the years, Shaq has to deal with those who really embrace the whole Hack-a-Shaq thing. AP Photo/Greg Wahl-Stephens 3. How does Shaq's feat compare to Wilt's? It's a lot more impressive, actually. We can show this a couple of different ways. For starters, Wilt stayed on the court virtually the entire game, averaging 45.8 minutes a contest for his career -- far more than Shaq's 36.0. As a result, he has played nearly 10,000 minutes more than Shaq even though he's been in fewer career games. Additionally, Chamberlain's era was much faster-paced than Shaq's, as mentioned above; teams in the 1960s routinely played games in the 120s, even without 3-pointers and with lower shooting percentages. Comparing apples to apples then, on a per-possession basis Shaq has been a far more prolific free-throw mason than Chamberlain. Indeed, even with those disadvantages in pace and minutes he might eventually pass Wilt. O'Neal is 813 misses behind Chamberlain's record and is piling up misses at a rate of about 200 a season. Should that rate hold up, he'll surpass Chamberlain in 2012, when he's 40. To do so, he'd need to play three more seasons after his current contract ends -- unlikely, perhaps, but not impossible either. 4. How much damage have the bricks done? On one level, you could argue that Shaq's career should be massively different. Per season, free-throw misses deducted nine points from Shaq's regular season player efficiency rating -- which means his already-gilded 27.1 career PER would be a phenomenal, stomping-everyone-including-Jordan 36.1. Of course, that logic relies on a completely unrealistic assumption, because it's presuming that he'd make all his foul shots. Instead, let's imagine a more likely scenario. Suppose Shaq had slowly improved so that by the midpoint of his career he was a 70 percent shooter from the stripe. That's reasonable for an NBA center, especially a big low-post center like Shaq. (By the way, if Shaq were a better shooter, it's likely his game would be fundamentally different in a great many ways -- he'd be stepping out, hitting jumpers from the high post, etc. -- that might or might not be good for his overall production.) Had that happened, his career mark would end up three-quarters of the way between 70 percent and the 55.3 percent combined he shot in his first two seasons, which would be 66.3 percent. That would certainly be helpful, adding nearly three points to his career PER and putting his career mark close to the exalted 30 mark. However, it's not clear that his outcomes would have changed much. The gain would have been concentrated on the tail portion of his career, especially the seven-year stretch between 2000 and 2006 when his teams won four titles and were serious contenders the other three years. But in two of those three seasons, his team was handled fairly easily when it was eliminated -- the only one in which you can imagine the outcome being different is in 2005, when his Heat lost narrowly to Detroit in a seventh game. So perhaps he would have won five titles instead of four. Maybe he would have had another Most Valuable Player award. But in the big picture, it's hard to see that Shaq has lost much from being a lousy foul shooter. In The Bonus More fun with 5,000 A few more Big Cactus points: • Shaq's teammate Nash has missed 253 free throws in his 883 NBA games. At that rate, it would take him 17,451 games to miss 5,000. If he played every regular-season game for 200 seasons, he'd still fall short. • Entering Dec. 19, the top 12 FT% shooters had missed a combined 4,995 free throws in 45,076 attempts (see chart). • If Larry Bird were to come out of retirement and miss his next 3,000 free-throw attempts (which would require him to shoot 0 percent for about seven seasons, based on his peak season of 492 free-throw attempts), he'd still have a higher career free-throw percentage than Shaq. • Shaq is currently 10th on the all-time scoring list; if he had missed only 4,000 free throws (corresponding to just 62 percent shooting), he'd be fifth. John Hollinger writes for ESPN Insider. To e-mail him, click here. ESPN researchers Lisa Brooks, Mark Simon and Matt Willis contributed to this article.