Back in the 1992 NBA Draft, the Orlando Magic struck gold by picking Shaquille O’Neal as their #1 pick. And the next year, they landed Chris Webber as the top selection. After a dream season for Michigan, Webber became the first sophomore since Magic Johnson to be a #1 overall draft pick. But C-Webb didn’t want to play alongside Shaq and Shaq influenced Orlando to trade Webber. While C-Webb got his wish fulfilled, Shaq broke Webber’s next big wish when they met on the court in 2002.

Chris Webber opened up on Best of Both Worlds with Flau’jae, where he reminisced about going toe-to-toe with basketball legends. Recalling his battles with Shaq and Kobe Bryant’s Lakers as part of the Sacramento Kings, Webber couldn’t hold back his admiration for Shaq’s dominance. “People don’t realize how dominant Shaq was,” Webber shared.

“He’s the best athlete by far that I’ve ever seen and it’s not just because he was tall. Because, I mean, his vertical, he was fast, he was strong, he was smart,” C-Webb further added. However, that showdown left a bitter taste for Webber, as his championship dreams crumbled in the face of Shaq and Kobe’s dominance.

“That series stopped me from getting a championship,” Webber reflected. The Sacramento Kings hit their stride in the early 2000s, finally bringing some serious heat to Northern California’s NBA scene. From 2000 to 2005, they notched at least 50 wins each season, with 2002 marking the peak of this golden era. The Kings came within a breath of the NBA Finals, battling Shaquille O’Neal and Kobe Bryant’s Lakers in a fierce Western Conference Finals. But the Lakers took it in seven games, crushing Sacramento’s dreams.

When people talk about that series, the officiating scandal often comes up. Former referee Tim Donaghy even hinted that Game 6 might have been tilted toward L.A. With stars like Mike Bibby, Chris Webber, and Peja Stojaković leading the charge, the Kings dominated—until 2005, when the playoffs drought began, lasting an NBA-record 16 seasons. A chapter C-Webb probably won’t be proud of.

Nonetheless, the sting of that particular defeat lingered long after, and he even used to text Kobe, jokingly asking, “Where’s my ring?” Though he never got that elusive championship, Webber found comfort in the respect he held for both Shaq and Kobe. While O’Neal crushed Webber’s dream this time, the Big Aristotle actually played a big part in fulfilling one of C-Webb’s wishes from his rookie year.

Shaquille O’Neal feels he and C-Webb would’ve been a great duo

For a rookie Webber, leaving Orlando Magic remained the right choice, as playing alongside Shaq wasn’t for him. In his words, “That turned me off… I don’t care if it is Michael [Jordan] or Magic [Johnson]. They’re the leaders, but the team is its own.” Webber’s philosophy was clear: he didn’t want to play under anyone’s shadow, regardless of their stature in the game.

To Webber’s relief, he was traded to the Golden State Warriors for Penny Hardaway and future draft picks, thanks to Shaq pushing for Hardaway. Diesel wanted to team up with his Blue Chips co-star, convinced they’d be a perfect match. Even now, Shaq occasionally reflects on the “what if” of pairing with Webber, imagining a partnership that could’ve dominated just as well.

Reflecting on those days, Shaquille O’Neal once admitted he saw himself in C-Webb’s game. “Watched him in college…minus three inches,” O’Neal said, noting Webber’s passing skills and physicality. But the trade’s deciding factor? Shaq’s connection with Penny, thanks to their time together in the Blue Chips movie.

Blue Chips, a sports drama starring Nick Nolte, cast Shaq as Neon Boudeaux, but there were creative conflicts early on. Shaq was reluctant because of the film’s restrictions on his character’s language and behavior. Yet, if he had walked away, he’d never have met Penny—a meeting that ultimately reshaped Orlando’s future.

To this day, Shaq can’t help but wonder, “What if C-Webb and Shaq would’ve played together?” He imagines the havoc they might’ve unleashed, saying they “probably could have done the same damage as Shaq and Penny.”