Trail Blazers

How the Portland Trail Blazers’ famous summer of 1999 could help the current team

By Rob Ryan

Sometimes the past is a good teacher. The Portland Trail Blazers can look back to one of their hallmark offseasons as a guide to improving the current roster.

Any Blazers fan old enough to remember will tell you that the 1999-2000 Portland Trail Blazers should have won the championship. The prior season (1998-99) saw a younger, highly talented team from Rip City overachieve to make it all the way to the Western Conference Finals. After a 4-0 sweep at the hands of the eventual champion San Antonio Spurs, many thought Portland just needed to keep the team together and incrementally get better.

The following summer, Portland management started to break their own mold, which took a young team with some roster deficiencies and made them league favorites to win it all. Let’s look at those moves and how a similar mindset could improve the current Blazers team.

Trading for an All-Star

On August 2, 1999, the Portland Trail Blazers made a move that replaced the team’s current highest scorer in Isiah Rider. They also sacrificed some of their depth, with Jimmy Jackson included in the deal.

In return, Portland received former All-Star guard Steve Smith Smith. He was considered the best player on an Atlanta Hawks team that finished twice as the second seed and no lower than fifth in four seasons with the Hawks. During that span, Smith averaged 19.3 points per game PPG).

The consolidation of talent to acquire the veteran Smith was an exciting move for the franchise. Portland added some much-needed experience to a team already catering to Greg Anthony over Damon Stoudamire to close out games. The trade also allowed a young backup shooting guard named Bonzi Wells to get more playing time. The 1-2 punch at the two-guard position from Smith and Wells became a nightmare for opposing guards to defend.

Signing an old enemy

On the same day that Portland traded for Smith, they also signed another former All-Star and a long-time rival. It was odd to see former Seattle Supersonics center  Detlef Schrempf in Blazers’ red and black. Though past his prime, Shrempf could still produce. The previous season he averaged 15 PPG on 47% from the floor and 40% from the 3-point line as the starting small forward for Seattle at the age of 36.

Signing him to a two-year, $4.2M contract was a steal for someone the Blazers thought was a starting forward. Before acquiring Schrempf, Portland was often playing power forwards or shooting guards out of position at the small forward spot. They brought in Schrempf to help rectify that issue.

Though he was offered more money from other teams, he ultimately chose Portland because he felt they were close to winning a championship. Also, location-wise, it allowed him to stay close to his Seattle-based home.

So the young inexperienced Blazers quickly upgraded their wing positions with two former All-Stars. Not bad for a team that just came off of a Western Conference Finals loss. Arguably the biggest offseason acquisition was yet to come. 

Next: Page 2 – The final piece

Bringing in the Championship Pedigree

Sometimes when teams make moves to upgrade the roster, other unexpected options present themselves later in the process. Six-time NBA Champion and 7-time All-Star, and Dream Team member Scottie Pippen wanted out of Houston. Portland was his preferred destination. Pippen probably doesn’t make that request if the Trail Blazers didn’t trade for Smith in the first place.

With Scottie Pippen voicing his preference about heading to Rip City, the Portland Trail Blazers gained a good measure of trade leverage. That resulted in Portland not including any of their top rotational players to complete a move. Therefore, the Blazers sent a package of Kelvin Cato, Brian Shaw, Carlos Rogers, Walt Williams, Ed Gray, and Stacey Augmon to Houston for Scottie Pippen. The Rockets eventually bought out Augmon, and he returned to Portland a few weeks later.

Pippen immediately supplanted Shrempf as the starting small forward. Shrempf moved to a bench that was now full of quite a bit of starter-level talent. The new-look Portland Trail Blazers had a nightmare starting five of Damon Stoudamire, Steve Smith, Scottie Pippen, Rasheed Wallace, and Arvydas Sabonis. Their bench was also deep with key contributors Greg Anthony, Schrempf, Brian Grant, and Bonzi Wells.

The Blazers were not just contenders but the favorites to win it all. In one summer of moves, their potential became actualized.

Next: Page 3 – Bringing it back to now


How is summer of 99 relevant to the current squad?

First off, that 1999-2000 team didn’t win the Championship. A fourth quarter choke job in Gave 7 of the Western Conference Finals against the Lakers led to more offseason changes in the following summers. Those later moves began to erode team chemistry. The Portland Trail Blazers became TOO proactive. They made a habit of trading out eventual stars like Jermaine O’Neil for veteran players who had already reached their ceiling like Dale Davis.

There is a happy medium in all of it. Portland shouldn’t regret any of the moves made in the summer of 1999. Most of them were to upgrade leadership and experience. The current Blazers squad is lucky enough that they already have leadership with Damian Lillard and Chauncey Billups.

They also have young talent with star potential in Anfernee Simons. Jusuf Nurkic is an above-average center, and high-energy players Josh Hart and Nassir Little come off the bench. The current team needs to start taking risks to accumulate talent and experience to merge with the rest of the roster.

That 1999 Blazers team traded away the team’s leading scorer (Rider) and best bench player (Jackson) to upgrade a starting position with Smith. His coming to Portland might have contributed to Pippen choosing Portland over the Los Angeles Lakers.

If the Trail Blazers solidify their four-spot starter with a big trade around the draft, more players will start thinking about Portland as a destination. If talent consolidation included Hart or Little, that could open up the Blazers’ ability to use exceptions to sign their replacements. It’s easier to fill out the bench when there is a starting five that appears to have a high ceiling. Elite teams always have an easier time finding inexpensive veterans.

In Conclusion

I think the team should look at past successes (and failures) without being afraid to take risks. It’s very easy to focus on lost assets without evaluating what doors might become open afterward. The Portland Trail Blazers might not have as much money cap-wise as they’d like fans to believe. However, they still have quite a few trade exceptions they could use to fill out a roster quite quickly. A big enough move pre-free agency would absolutely give them more options to use with the exceptions.

Keep an eye on what Portland does during the draft and before free agency starts. Wasted time could point to a long summer with only incremental improvements at best. It’s time to see what kind of guts this management team has.

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Rob Ryan