May 28, 2026 9:51 PM
By weaponizing volatility and targeting the future uncertainty of aging rivals, Joe Cronin has transformed Portland into an asset powerhouse positioned to exploit the NBA’s flattened lottery odds.
A few years ago, a lot of people questioned what the Portland Trail Blazers were doing.
Fans were frustrated. National analysts called the team directionless. And when Portland traded away Damian Lillard, many assumed the franchise was simply starting over without a real long-term plan.
Now?
The Blazers suddenly look like one of the most asset-rich teams in the NBA.
Portland currently owns or controls seven potential first-round lottery tickets in the new flattened lottery era:
- 2027 Portland
- 2028 Portland
- 2028 Milwaukee
- 2028 Orlando
- 2029 Boston
- 2029 Milwaukee
- 2029 Portland
And honestly, it is starting to look like Joe Cronin saw this entire thing coming before everyone else did.
Because when you step back and look at the timeline, the strategy becomes obvious.
Cronin did not just collect picks randomly. He targeted future uncertainty.
The Milwaukee picks once looked far less interesting because the Bucks were expected to stay competitive for years with Giannis Antetokounmpo and Damian Lillard together. But things change fast in the NBA. Lillard suffered a major injury, Milwaukee’s roster aged quickly, and now the long-term future of the franchise feels far less stable than it did when the trade originally happened. Portland controls major Milwaukee-related draft positioning in 2028, 2029, and 2030.
Then there is Boston.
The Blazers acquired Boston’s 2029 first-round pick through the Jrue Holiday trade, and suddenly that pick looks far more interesting than it did initially. Boston’s core will be older by then, the financial pressure on the roster is growing, and the NBA changes dramatically over four-year stretches.
Even the Orlando pick has upside.
The Magic are talented, but the flattened lottery odds make future picks significantly more unpredictable than they used to be. A single disappointing season, injury stretch, or roster shakeup can suddenly move teams into lottery territory much faster than before.
That is what makes Portland’s asset collection so fascinating.
Cronin was not necessarily betting that all these teams would collapse completely. He was betting on volatility.
And in the modern NBA, volatility wins trades.
The flattened lottery odds changed everything. Teams no longer need to completely bottom out for picks to become valuable. Even mediocre or slightly disappointing teams can suddenly jump into favorable lottery positions. That gives future picks more value than they had during previous NBA eras.
Meanwhile, Portland still has its own young core developing with players like Scoot Henderson, Deni Avdija, and Shaedon Sharpe.
That is the scary part for the rest of the league.
The Blazers are not just sitting on draft picks. They are sitting on flexibility.
They can use those picks to draft talent, package them in a blockbuster trade, or wait for another desperate team to collapse.
And suddenly, the question around Portland is changing.
People are no longer asking what Joe Cronin is doing.
They are starting to ask how far ahead he already was.
Comments
Powered by RoundtableAn AI/DeFi-powered Enterprise Media Operating System. Learn more at Roundtable.io.© Roundtable 2026. By using this site you agree to the Terms of Use and Privacy Policy


