ESPN’s new docuseries left us with a cliffhanger at the end of Night 1, as Scottie Pippen had demanded a trade from the Chicago Bulls during the 1997-98 season—a season Phil Jackson aptly named “The Last Dance.”
We all know that Jerry Krause and the Bulls kept Pippen on board through the trade deadline and went on to win their sixth title of the Michael Jordan era, but with Jackson’s tenure over, MJ’s retirement imminent and Scottie’s distaste for how management handled the rebuild, the dynasty was done and the league’s balance of power was about to shift back to the Western Conference.
Fast forward a year, and Pippen had played 50 games for the Houston Rockets, but once again, his time with a team had clearly come to an end. After rumors began to swirl that Scottie wanted to reunite with Jackson as a member of the Los Angeles Lakers, the Portland Trail Blazers, in October of 1999, swept in and landed the forward with the Hall of Fame resume.
Although it looked for a moment as if Portland was planning to flip Pip to L.A. for Glen Rice, Trader Bob Whitsitt opted to keep Pippen on board in pursuit of a championship.
Scottie’s time with the Blazers didn’t result in a title, but it was an unforgettable run, for better or worse, and he was one of just many legends to give Rip City a try before calling it a career.
Scottie Pippen (4 seasons, 1999-2003)
Thinking back on Pippen’s first year with the team is to return to one of the most painful moments in franchise history. After a 1999-00 campaign in which Pippen averaged 12.5 points, 6.3 rebounds and 4.9 assists over 82 games, the Blazers finished third out West en route to its second conference finals in as many seasons. But the good times didn’t last.
What unfolded was a seven-game series fans will never forget. More specifically, a Game 7 collapse unlike many in league history and the accelerator for the Blazers’ crash from contention.
Pippen would go on to say years later that the Blazers needed someone to take over the game and take over the offense when all momentum shifted to the Lakers. He admitted it should have been him, but that as a first-year guy on a roster with a vastly different collective career arc, he was hesitant.
It wasn’t all bad times in Portland, and the truth is that Scottie likely gave Blazers fans an extra reason to tune by simply being a legendary player suiting up for the good guys.
But when it came down to it, the 2000 Western Conference Finals proved to be everyone’s make-or-break moment of that Blazers dynasty. Pippen played a few more seasons, but this is the one we’ll never forget.
Steve Kerr (1 season, 2001-02)
Steve Kerr, another prominent member of the Chicago Bulls dynasty and owner of one of the biggest shots in their franchise’s history, also spent some time in Portland. His was short lived, but he did overlap with Pippen during his lone 2001-02 season.
The deal that brought Kerr over to the Trail Blazers also included eventual fan favorite Derek Anderson. To acquire the two, the Blazers sent back Steve Smith, who had been with the team since Pippen arrived ahead of the 1999-00 campaign.
Carmelo Anthony (1 season—so far—2019-20)
Carmelo Anthony was exactly what the Blazers needed this season.
No, not as far as players who you over the top are concerned. He never elevated the team to true playoff status and the roster needed impact more than it needed celebrity.
But it was Carmelo’s celebrity—and more importantly the respect he’s earned from players across the league—that gave this team and this fanbase energy. He had come from rough times in Houston, Oklahoma City, and, if you want to be fair, New York. He was a comeback story waiting to happen in the form of a surefire Hall of Famer. (If you don’t believe Carmelo Anthony is a Hall of Famer, you’re overvaluing rings and undervaluing his impact. And by the way, you need to look at some of the other names inducted throughout history. Melo’s case is easy.)
Carmelo gave this team a jolt upon his arrival, and he made the Blazers downright watchable again. Up to the point of his arrival, they hadn’t been.
Andre Miller/Marcus Camby (2 seasons, 2009-2011)
To call Andre Miller a legend might be a bit overkill even by his own evaluation. Same goes for Marcus Camby.
To Portland, though, they were two big-name, important pick-ups who ended up leaving as fan favorites. Miller had himself a 52-point game, which was maybe one of the more unexpected 50-burgers cooked up in league history. Camby ended up becoming the focal point of the offense one night and earning MAR-CUS-CAM-BY chants from the home crowd.
Neither of these singular instances alone earn them legend status, but as far as familiar names go, Blazers fans became proud of these two during their times with the franchise despite being better known for their prior stints in other cities.
We’ll take this moment to also honorable-mention Gerald Wallace, who fills a very similar bucket. His career makes for an interesting case study, but his time in Portland was short-lived. Despite giving the Portland fan base a serious jolt, he was off to Brooklyn a year later—the same trade-deadline blowout sale that saw Camby land with the Houston Rockets, ending his run with Rip City in 2012.
Jamal Crawford (1 season, 2011-12)
Jamal Crawford is a basketball legend. The fact that he’s unemployed while still seemingly wanting back in the NBA is a shame, and although his window is nearly closed, it seems some team could use his unique offensive skill set.
Crawford’s one season in Portland became one of the more memorable in recent franchise memory, as he and Raymond Felton were the two biggest trade chips the team had to offer in the disastrous Year 1 post-Brandon Roy experiment.
As it turned out, Crawford and Felton would survive the league’s annual talent swap, but Camby and Wallace found themselves off to new teams. Even Greg Oden and Nate McMillan were sent packing that same day, making it undoubtedly the weirdest trade dadline in team history.
Lenny Wilkens (1 season, 1974-75)
Before Lenny Wilkens found himself in Portland, he was a nine-time All-Star. He only spent one year with the Trail Blazers, but he made sure to make it count taking over the role of player-coach and even sticking around as coach one extra year.
Juwan Howard/Kurt Thomas (1 season each, 2009-10/2011-12)
Juwan Howard and Kurt Thomas fall into the Andre Miller/Marcus Camby category here to an extent. But Howard, in particular, has legendary status in his own right as a prominent member of Michigan’s Fab Five.
Both big men were longtime journeymen who’d had some of the more stable NBA careers you can think of. Before landing in Portland, Howard had played 15 seasons for nine teams including the Mavericks and Nuggets twice. Thomas was entering his 17th season and joining his ninth team.
Thomas never made an All-Star Game but was one of the league’s workhorses you felt good about having as a mentor and a glue guy. Howard was an All-Star in 1996 and eventually won two titles with the Miami Heat after leaving Portland.
Ahhh, here we go. True legend status.
Although it’s tough to see an argument that places Shawn Kemp in the NBA’s 50 Greatest conversation (Top 100 may be a more reasonable starting point), he’s an unforgettable figure in NBA history. His intensity and cockiness was unmatched. His athleticism unfair for his size. His dunks, the literal stuff of legend.
Kemp, like so many, became one of Jordan and Pippen’s victims at one point in the Finals. And while his time in Portland was largely forgettable, he once again gave the Portland fan base a memory of rooting for a once-rival who’d end up wearing black and red.
Although Pippen has an important history with Seattle basketball, having been drafted and traded on draft day by the SuperSonics franchise, Kemp represents the true I-5 rival to convert.
He, Detlef Schremph and Nate McMillan to name a few—not to mention the silky smooth voice of broadcaster Kevin Calabro.