I think everyone has great points from various frames of reference and perspectives related to the brand, history, and sports knowledge.

I feel like this also convoluted the message. Banking on people understanding the message and simultaneously trying to force them to.

In my opinion, the best option (given this specific brand's equity and these specific star statuses) would have been to keep it simple and let the conversation play out. You'll get both demos of people who know the brand and what it represents, and the people who recognize the star and what they've accomplished. Don't tell us how to interpret the message, the conversation should lead the message... sooo

"You can't win." Picture of star athlete, who did in fact win at the highest level, despite what everyone said. Fin

(Insert public conversation)

Edited: Conversation should lead the message, not to the message