I doubt it. Jordan got rich off his national endorsements: Gatorade, Coke, Hanes, Chevy, McDonalds and of course, the biggest of them all - Nike, located right here in little ole Beaverton, OR. It was Nike and the Air Jordan line of shoes and clothing that transformed Michael Jordan from an athlete into a brand. He STILL makes over $100 million per year off his Nike deal. Small market, large market, it would not have mattered, As long as he was winning scoring titles, MVPs, dunk contests and eventually championships, he was going to be the richest athlete in the history of the world. No matter where he played, his local endorsement deals would have always been small peanuts compared to his national deals.
It was much less common for star athletes to demand trades back then. Most remained loyal to the teams that drafted them. In Jordan's case, with all his national endorsements, there was no incentive to demand a trade to a larger market. And, in this case, there would have been a big incentive to stay in Portland - winning. Jordan was, perhaps, the most competitive athlete in the history of team sports. He always played to win and drove his teammates to do the same. Outside of Jordan himself, those early Bulls teams were pretty devoid of talent. The Bulls didn't draft Pippen until Jordan's 4th year in the league - which is also the first time Michael advanced past the first round of the playoffs. In Chicago, Jordan had to wait 4 years until he was paired with another Dream Teamer and one of the 50 Greatest Players of all time. In Portland, he had one ready and waiting for him to start his rookie year. With his length and athleticism, Clyde could have easily played small forward next to Jordan at the 2. The Bulls didn't make it to the finals until 1990-91 - Jordan's 7th year in the league. The Blazers made the finals a year sooner - without Jordan. With him they would have made it even sooner. Portland won 48 games and were the 3 seed in the Western Conference playoffs the year before Jordan was drafted. The Bulls won 27 games and missed the playoffs. The Blazers minus Bowie simply had a lot more talent than the Bulls minus Jordan. Plug Jordan into that Blazers roster and he would have won more and would have won sooner. And, for Michael Jordan, winning was always what mattered most.
BNM