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

Portland Trail Blazers
Joe Cronin, Portland Trail Blazers General Manager.

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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