April 22nd, 2026 | Isaac Garcia | Sports Editor
While the Portland Trail Blazers are currently in the midst of their first playoff series since 2021 against Victor Wembanyama and the San Antonio Spurs after defeating the Phoenix Suns 114-110 in the play-in tournament, some fans are taking the time in between to reflect on the era of Blazers basketball often referred to as the “Jail Blazers” era. On April 14, Netflix introduced the next installment of its “Untold” series with a documentary-style episode focused on the team, with feature interviews from players Rasheed Wallace, Damon Stoudamire, Bonzi Wells and the general manager of the team at the time, Bob Whitsitt.
The documentary opens with the hiring of Whitsitt after a successful tenure with the Seattle Supersonics, which coincided with the Blazers needing to retool after franchise legend Clyde Drexler was no longer a member of the team, as well as Microsoft co-founder Paul Allen purchasing the franchise and looking to start winning immediately. Whitsitt, understanding that he needed to retool the team without tanking and completely bottoming out while also not relying on big name signings — since Portland isn’t a destination star NBA players typically seek out — he began to look for players in trades that had some sort of “problem,” therefore making them possible to bring on for lower contracts and giving up fewer assets. Portland was trading for players at such a high frequency that Whitsitt earned the nickname “Trader Bob,” and two majorly successful deals that brought Wallace and Bulls legend Scottie Pippen to Portland quickly gave way to a meteoric rise that put the Blazers in the 2000 Western Conference Finals against the Kobe Bryant and Shaquille O’Neal-led Los Angeles Lakers. In addition to Wallace and Pippen, the Blazers also brought in Stoudamire, who was a local star and an alumnus of Wilson High School in Portland. Bonzi Wells was also acquired in a draft-day deal. Wells — who grew up in Indiana — said he had no idea where Portland was when his agent told him he would be sent there.
Unfortunately, the series against the Lakers in 2000 is a story Blazers fans know all too well. In a make-or-break Game 7, the Blazers came out firing and in the fourth quarter held a 15-point lead and seemed just minutes away from their fourth finals appearance in franchise history. The team would then inexplicably miss 13 shots in a row while Bryant and O’Neal willed the Lakers back into the game, stealing a victory that seemed all but certain for Portland. Los Angeles then went on to sweep the Indiana Pacers, an opponent many to this day feel would’ve been no match for the Trail Blazers.
While this isn’t necessarily considered part of the “Jail Blazers” era, the documentary takes the angle that it was the catalyst. To be so close to the ultimate goal but come up short quietly upended the organization. While the players were ready to go at it again with essentially the same team, Whitsitt lived up to the “Trader Bob” nickname and continued making moves, adding Sonics legend Shawn Kemp via trade. Wells mentions having an issue with the trades Whitsitt made, which gave up key depth for individual players.
Around this time is when the off-court issues really began. A story is told about Stoudamire and Wallace driving themselves back to Portland after a game in Seattle instead of riding with the team bus. While that’s no problem within itself, the two would be pulled over in Centralia and cited for possession of marijuana in a time when its usage was still very much illegal. In his interview, Wallace describes it as a movie scene as the entire Trail Blazers team bus passed the two whilst they were still stopped on the side of the road.
Stoudamire would also run into further marijuana related offenses, with one well-known incident being when he was caught trying to dispose of it prior to boarding a plane in Phoenix and getting arrested. Stoudamire himself also brought up a time when he returned to his home in Lake Oswego and felt as though someone had been through his house, as multiple things had been misplaced despite Stoudamire living alone. After the police came to the residence, they searched his home and found grams of marijuana in the residence, which led to his arrest yet again. Later on, Stoudamire would actually have the chargers dropped on account of the search being illegal. Stoudamire reveals in the documentary that, after this incident, he always felt as though he was being watched, and that’s why, even after his career, he seldom returns to where he grew up. The documentary also dives into the extreme temper of Wallace, who would set a single-season record for technical fouls and regularly be at odds with the media and league officials.
The most controversial of all, however, was the addition of Ruben Patterson, who was a registered sex offender at the time he joined the team. In the documentary, Whitsitt stands behind his decision to add Patterson, arguing that he had “done his time” and that it was the best choice for the team. At the time, this seemed to be the final straw for fans already tired of the team’s antics and the documentary makes a point of showing fan interviews expressing distaste and frustration as well as empty seats in the Rose Garden. Wallace also mentions that the move negatively impacted the team chemistry.
As attendance and team performance slowly declined, it became apparent that things needed to change. Owner Paul Allen purchased the Seattle Seahawks as well in the ‘90s and later put Whitsitt in charge of football operations. Whitsitt — who was a bit overwhelmed and frustrated by all the responsibility — would step down as the Blazers’ general manager. His successor would then make a point of rebranding the team’s image, trading Stoudamire, Wells and Wallace, among others. The Wallace trade would actually turn out to be among the most important of the decade, as joining the Detroit Pistons would net him an NBA championship, finally defeating the Los Angeles Lakers, just not in Portland.
The documentary ends with a reunion of the 1999-00 team at a 2025 Trail Blazers game, with Rasheed Wallace declining to join, explaining that the city of Portland didn’t want him around when he was there, so he doesn’t want to return now. Stoudamire — now the Georgia Tech men’s basketball coach — is in a clip with Wells where he says that he’s mainly going to the reunion for him, as he started his career in Portland and experienced early adulthood there. Wells has a powerful moment where he looks out at the city from his hotel room and reflects on how strange it is that the place he used to know so well and call home seems almost foreign now. It’s also mentioned that Wells had never even been in any sort of legal trouble, but that he dealt with the stigma of being part of the team as much as anyone else.
The documentary as a whole is an interesting look at a bit of local history and an era most Blazers fans would probably like to forget. As mentioned above, it’s currently streaming on Netflix. This Friday, April 24, the current Trail Blazers will also be taking on the Spurs in Game 3 of their first-round playoff series at the Moda Center.
Contact the author at howlsports@mail.wou.edu
