13. Trade for Aaron Gordon?
The Portland Trail Blazers were rumored to be interested in Aaron Gordon for years before he was traded to Denver Nuggets in 2021. They viewed his versatile skill set and defense as the perfect fit around Damian Lillard, and ESPN viewed this as the biggest recent what-if in team history.
The plot lines go like this. It was Denver who knocked Portland out of the playoffs in the first round just months after acquiring Gordon. The 6’8 forward averaged 12.5 points, 6.5 rebounds, and 2.3 assists in 30.1 minutes per game during that series. The Nuggets did not have Jamal Murray, and the door was open for Portland.
Now, imagine Gordon on their team. The Blazers would have advanced to round two, and the race was wide open.
Denver lost to the Suns in the second round, and Phoenix won the Western Conference that year. With Dame’s ability to ascend in the biggest moments, it could have been the Trail Blazers upsetting the Suns and Clippers to play the Bucks in the NBA Finals.
Instead, Gordon helped the Denver Nuggets win the title in 2023. With the 6’8 forward, the Blazers likely make a deep run in 2021 and are better positioned to keep Damian Lillard happy in Rip City, but they could not complete a deal. Anfernee Simons was rumored to be the hold-up. What-if Portland had included him in the trade? Who knows.