Jackson compared the two legendary centers Wednesday night in Glendale at the Alex Theatre at his "Live Talks Los Angeles" event.
"Shaquille didn't have quite the same athleticism that Wilt had," said Jackson. "He had the bounce and he had the speed, but he didn't have the endurance."
As detailed in his memoir, "Eleven Rings: The Soul of Success," Jackson told O'Neal that Chamberlain's greatest accomplishment came in the 1961-62 season when he averaged 48.5 minutes a game.
Jackson challenged O'Neal in their first season together (1999-2000) to get in better physical condition to improve his endurance.
While defending Chamberlain, Jackson found some techniques that worked.
"One of the things we were taught, just get in Wilt's path. He doesn't like the offensive foul," said Jackson on Wednesday. "If you take his shoulder and you fake an offensive foul, take the charge so to speak, he really would stop being aggressive. That was the one thing that was kind of a limitation in Wilt's game."
In other words — flop.
O'Neal was faster from one end of the court to the other, at least to the offensive end.
"Shaq was a post sprinter," said Jackson. "He'd go and get in the lane."
Chamberlain took a much slower path.
"Wilt was never much of a post sprinter. He used to take his time," said Jackson. "When he rebounded, a lot of times he'd make the guards come back to him to get the ball — so he'd be down there when the ball got to the other end of the court."
O'Neal also had a move that Chamberlain didn't use — and vice-versa.
"[O'Neal] had a jump hook whereas Wilt didn't have a jump hook, he had an array of shots, he had a hook, a finger roll and a turnaround jump shot," said Jackson. "[Chamberlain] led the league in assists one year."
They both had the same flaw in their games.
"Free-throw shooting? [Issues] on both sides," said Jackson. "Even then, at that time, you fouled Wilt if he was underneath the lane."
Chamberlain won two titles, his first in 1967 with the Philadelphia 76ers and in 1972 with the Lakers.
O'Neal helped lead the Lakers to three titles from 2000-2002. He also won a fourth with the Miami Heat in 2006.