3. Sherman Douglas, Point Guard
No one had a more difficult time in terms of win-loss record in the regular season and the playoffs in his professional career against Jordan and the Bulls than point guard Sherman Douglas. As a serviceable point guard, but also somewhat of a journeyman in the NBA, Douglas did run into a ton of trouble against Jordan.
Douglas did spend most of his career with the Boston Celtics, Miami Heat, New Jersey Nets, and the Milwaukee Bucks. Many of those teams were frequent opponents of Jordan and the Bulls in the late 1980’s and throughout the 1990’s. And of that, Douglas spent the bulk of his career with the Celtics (around five years).
He did have more than 10 years in the NBA, with pretty solid career averages for a journeyman point guard. In more than 750 career regular season games played, Douglas averaged 11.0 points per game, 2.2 rebounds, and 5.9 assists. In general, he could be a pesky defender, averaging one steal per game for his career. He also registered a career assist rate in the 20’s and an offensive box plus/minus rating just shy of 1.0.
It was almost impossible how well Jordan and the Bulls were able to do against Douglas in his career, though. No opposing player to Jordan has as many losses, while staying winless, in his career as Douglas. Jordan was 30-0 in his career between the regular season and playoffs combined against the 6-foot-1 point guard. Douglas also was held around one point per game under his career average, and had twice as many turnovers and around half as many assists, in those 30 tries against MJ.