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Damon Stoudamire reflects on the infamous Portland ‘Jail Blazers’: "It does kind of sting when you look back at it"

Damon Stoudamire recalls what made the Portland Trail Blazers so special as a team
Damon Stoudamire recalls his time with the Portland TrailBlazers

Damon Stoudamire had a good run with the Blazers

In the post-Michael Jordan era, the Los Angeles Lakers dynasty resurged in the form of the dynamic duo of Shaquille O’Neal and Kobe Bryant. Of course, LA had their fierce rivals that made things difficult as well—The Portland Trail Blazers.

The leading championship contenders

From the late 90s to the mid-2000s, the Blazers were among the most talented and stacked squads in the NBA. Led by versatile big man Rasheed Wallace, former Rookie of the Year Damon Stoudamire, and many other great role players, Portland reached the Western Conference Finals twice during those years.

Ultimately, the then-Blazers were one of the leading championship contenders. But as the team found success on the court, the players constantly made the headlines for off-court troubles and run-ins with the law as well.

This dark period in the Portland franchise is known to this day as the infamous “Jail Blazers” era.

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To name a few incidents that happened at the time, Damon Stoudamire had been involved in three different marijuana-related incidents in two years, resulting in fines and suspensions. In April 2001, All-Star forward Shawn Kemp was prompted to end his very first season with the Blazers to check himself into a drug rehabilitation center for cocaine abuse.

In November 2002, Rasheed Wallace and Stoudamire were charged with misdemeanor and marijuana possession. The pair agreed to religiously attend drug counseling and stay out of trouble to have the charges dropped.

Even then-Blazers newcomer Zach Randolph also had his fair share of legal troubles as he was charged for underage drinking in May 2002. Randolph and Ruben Patterson got into a fight during practice almost a year later, resulting in Patterson’s eye socket getting broken.

Stoudamire feels like they underachieved

Reflecting on the subject, Stoudamire insisted that everyone has already moved on from it, but he also admitted that they had a pretty “good run” back then. As for whether their troubles somehow hindered them from achieving greater things or not, “Mighty Mouse” candidly confessed, it absolutely did.

“I honestly don’t put a whole lot of thought into it, but it does kind of sting when you look back at it,” Stoudamire exclusively told Oregon Live in 2020. “Well, we went to the conference finals two years in a row. Did we underachieve? No question. I think we had a championship team. We didn’t do what we needed to do. Did some off-the-court problems contribute to that? No question. It did.”

“But I think we had a good run here,” he added. “Probably more than anything for me, what stands out the most, when you look around at sports, people move on. But I don’t know. We get caught up in this time warp, they always talk about what ifs, what ifs, what ifs. I get it. But we actually did go to two conference finals. We did have some good seasons, had some 50-win seasons, did some pretty good things here. But no one talks about that, no one seems to remember that.”

Looking back at all these events, we can only wonder what Portland could’ve accomplished had the “Jail Blazers” never existed and players were more professional and dedicated to staying out of trouble. 

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