Sometimes a stray comment at an awards show becomes more than a throwaway line, especially when it pulls together two sports worlds that rarely meet. That is what happened at ’s ESPY Awards, where Anna Leigh Waters offered an unexpected thought about LeBron James and the Portland Trail Blazers.
According to a story by James H. Williams of, Waters said the Trail Blazers were a possible destination for James, framing the discussion around an NBA free-agency question rather than a simple aside. Her answer was cautious at first — “I don’t know,” she said — before she connected the dots to the person who owns her league.
Waters pointed to Tom Dundon, saying she knew “the owner of the professional pickleball league just bought the Portland basketball team, the Trail Blazers, and I know he’s trying to get (James), so we’ll see if that happens.” That is what made the comment notable. It was not just a celebrity talking about the NBA. It was a professional pickleball player referencing the owner of her league and tying him directly to one of the biggest names in basketball.
The idea itself is still just that — an idea. But the setting gave it real intrigue. The ESPY Awards are built for crossover moments, and this one had a clear hook: Portland, LeBron James and a new ownership connection through Tom Dundon. Even without anything concrete beyond Waters’ remarks, the comment was enough to turn a routine awards-night question into a small but widely relevant sports story.
For now, that is the right way to read it. Waters did not present a finished announcement or a firm prediction. She raised the possibility, and in doing so, put the Portland Trail Blazers into a conversation they were not expected to occupy at the ESPYs.
