Throughout the history of the Association, there have been countless deals that could make or break a franchise. Whether it was snagging a sleeper pick in the draft or handling some clever maneuvering in the offseason, it has always been crucial for a team to maximize its assets and build toward success. Lifting that Larry O'Brien trophy in June.
However, if you ask Charles Barkley , there is one franchise that was so spectacularly bad at it that it ultimately cost him at least one Championship.
That team was his Philadelphia 76ers , and the fateful moment, where all came crumbling down, came during the 1986 offseason.
"I'm being serious for one second now… I've been bitter and angry because that cost me at least one Championship, probably two. Because, I was just becoming a star, we had the number one pick in the draft, and me and the guys went out to celebrate that night. This is night before the draft. And we got drunk as hell…" Barkley recalled in his recent appearance on the Bill Simmons' podcast.
Understandably, Sir Charles was feeling himself. Entering his third year in the NBA, he was already a member of a second All-NBA team and ranked sixth in MVP voting for the 1985–86 season. Securing the No. 1 pick, which was undoubtedly going to be Brad Daugherty , felt like hitting the jackpot. But celebrating a little too early proved costly, as a single phone call in the middle of the night changed everything.
It was longtime 76ers reporter Phil Jasner with the uneasy task of delivering the bad news to their star player.
"Phil, there is no way the Sixers are that stupid to trade away the No. 1 pick in the draft. He says, 'And it gets worse.' 'Well, it can't get any worse than that," Barkley added, while saying that he had to get a nice long shower session before getting all that information in.
"It was about 5:30 in the morning, 'Phil, explain to me what's going on,'" Charles continued the story. "He says, 'You guys have just traded the No.1 pick in the draft to Cleveland… And you guys traded Moses Malone to the Washington Bullets at the time for Jeff Ruland.' Rutland didn't play in two years…"
Unfortunately for Barkley, this wasn't some fever dream or the fog of alcohol talking; it was the harsh reality for the entire organization. The Sixers blew their golden ticket to dominate the Association for at least a decade.
Larry Bird's Boston Celtics were on their last legs, and Magic Johnson and the Lakers weren't getting any younger either. With the right moves, it could have been a battle between the Chicago Bulls , Detroit Pistons , and a Sixers team built around Barkley, Moses Malone and Daugherty.
Malone did so much for Barkley in his professional career until that point, so this one stung a bit more. He was meant to bridge the gap until Chuck and Brad could take over the reins completely. But it wasn't meant to be. And yes, you guessed it, Sir Charles still resents that decision from the organization.
"From that point on, I was so angry, I had to spend another four years sucking in Philly," he concluded.
A couple of bad decisions have kept the 76ers stuck in the middle of the pack, and Barkley? Ringless and still bitter. And, honestly, who could blame him?
This story was originally reported by Basketball Network on Sep 4, 2025, where it first appeared in the Latest News section. Add Basketball Network as a Preferred Source by clicking here.
