(This achievement is acquired playing in the "My player" mode)
This achievement is actually tied to your leaguewide popularity. When you answer questions in your postgame news conferences, answer with arrogance, which will almost always result in a bump in leaguewide popularity. You will first be contacted by Jordan for sponsorship, then be put on a billboard, then be featured on a magazine cover. The fourth progression will be a letter from Jordan to design the shoes. If you have been answering arrogantly at the news conference every time, you should expect to get it after about 40-50 games.