During the early, to mid-2000s the Portland Trail Blazers were known as the Portland Jail Blazers. Players like Rasheed Wallace, Damon Stoudamire, Zach Randolph, Qyntel Woods, Darius Mieles, and Bonzi Wells ran into frequent problems with the law.
During his time with the Blazers, Rasheed Wallace regularly averaged over 30 technical fouls per season. In the 2000-2001 season, he logged 41 technical fouls, a record that still holds up to this day. He was charged for marijuana possession a couple of times and suspended for seven games in 2003 for threatening referee Tim Donaghy in an incident after the game.
Damon Stoudamire had a couple of marijuana charges as well. One of them famously happened at an airport in 2003 after he tried to pass through the metal detector carrying the weed wrapped in aluminum foil. He was suspended by the team and fined $250,000.
Then, Ruben Patterson remembered mostly for his off-court problems. In 2001 he pleaded guilty to attempting to rape the nanny; he was sentenced to 15 days of jail and labeled as a registered sex offender. He was convicted of misdemeanor assault by attacking a man who scratched his car outside of a nightclub.
Qyntel Woods was arrested for speeding and using his basketball card as an ID because he didn’t have his license. He was kicked off the team because of animal abuse — he was allegedly involved with a dog-fighting group.
Darius Miles and Bonzi Wells had problems with the coach Cheeks. In 2004, Miles verbally assaulted his coach with racial slurs, while Bonzi was also suspended for assaulting a coach but even physically assaulting a referee.
Zach Randolph had a wide range of accidents, including getting arrested with weed, physical assault, and DUI (driving under the influence). In 2003 he punched Patterson at practice and broke his face because, according to the other players, he hated how Patterson had always bullied the younger teammates.
In all that disfunction, they were still able to win 50 games in multiple seasons. (2000: 59-23, 2001: 50-32, 2002:49-33, 2003: 50-32). They made the conference final in 1999 and 2000. However, after 2003 they didn’t do so well anymore; rebranding was necessary, so they traded players such as Bonzi and Wallace.
The Golden State Warriors coach, Steve Kerr, played for Blazers in the 2001-2002 season. He recalled, “What a great experience that was. That was awesome. That might have been the most fun year I have ever had in NBA, to see the dysfunction. I had never seen it anywhere else.”