By now, most people know the broad strokes of Dennis Rodman 's early life. You cannot really tell that story without the word chaotic coming up. Yes, it's the same word that would later come to define his public persona.
There's no shortage of early incidents that reflect that, but one stands out more than most.
It came during a stretch when the future Hall of Famer was working as a janitor at Dallas/Fort Worth International Airport — a job that didn't last long. For a wild reason, that was.
Playboy magazine filled in the details in a 1997 profile about the Chicago Bulls star.
Rodman hit rock bottom at 20
On the court, Rodman was a thief in the best sense.
The volatile 6'7" forward picked pockets and hunted boards. Even when he didn't come up with the ball, he still knocked opponents out of rhythm. Over his 14 years in the association, he had multiple games with four steals — the most he ever recorded in a single night .
Off the court, though, Dennis had already been stealing in a far less admirable way years earlier. That came through most clearly in the story Playboy told.
After finishing South Oak Cliff High School, Rodman worked as an overnight janitor at DFW Airport. It was supposed to give him, at 20, some structure. But as you might expect, given his reputation, The Worm went the other way.
It all came to a head one night when he "used a broom handle to pilfer 50 watches from a closed gift shop."
As with most airports, there was CCTV footage, and it quickly identified him. Consequently, Rodman spent a night in jail and was fired from his janitor job.
According to Playboy, it left the New Jersey native, already short on options in life, at "rock bottom."
Related: "Escaping bullets to the NBA" - Stephon Marbury reflects on his Coney Island roots
From jail time to a luxury watch collection
Rodman could have avoided all of this with a bit more common sense. Of course, he should not have stolen in the first place. But even if he had made that decision, the presence of CCTV cameras alone should have been enough to make him reconsider.
It didn't, though, which makes the whole thing look as brazen as it was foolish. That said, Playboy asked The Worm if he knew the whole airport was covered in cameras. They also asked if he really thought he wouldn't get caught doing something like that.
"Maybe I did it to get caught," the five-time NBA champion responded. "Sometimes in life you have to light some dynamite, see if it blows up."
In a way, it sounded a lot like the Rodman who came later — driven by impulse, conflict and attention.
Some of those very instincts surfaced again in 2019. Back then, the two-time DPOY was linked to another alleged theft.
The owners of VIBES Hot Yoga claimed he had distracted the staff while his companions stole clothing and a crystal. Dennis, however, denied stealing anything. He simply said the group had been allowed to take items after asking for help moving the crystal art.
As for the watches, Rodman eventually made enough to buy his own.
According to "Rubber B," his collection includes a Rolex Submariner, a Hublot Big Bang, a Swatch Cool Pack Chronograph, and a custom Rolex GMT-Master II by Skeleton Concept with a black-and-red carbon case.
Safe to say, those were well out of reach back when the NBA legend was working as a janitor at DFW Airport.
This story was originally published by Basketball Network on Jun 13, 2026, where it first appeared in the Off The Court section. Add Basketball Network as a Preferred Source by clicking here.

