Bowie
In 1984, the Blazers were on the horns of a dilemma. They thought they needed a big man, but something about Sam Bowie was starting to scare them as draft day approached, especially after they gave him a seven hour physical.
Also, Stu Inman couldn't forget Bob Knight's endorsement of Jordan at the Olympic Trials.
The night before the draft, they decided that Bowie wasn't in their best interest, and that they didn't need Michael because they really liked the young Clyde Drexler. So, they sent G Jim Paxson, F Calvin Natt, and the second overall pick to the Clippers for F Terry Cummings, the 1983 Rookie of the Year.
What really made this worse from the Clipper perspective is that they would make another dumb decision which would be the hallmark of their organization in future years. They didn't even consider Jordan. They took Bowie because they wanted to replace Bill Walton.
Bowie started out his career okay, and played 73 games in his first year. After that, though, the injuries started to mount up again. He only played in 50 games the next two years, and then he missed a full year in 1987-88. He eventually was traded to the Bulls for Stacey King, and would be a good contributor off the bench in teaming with Bill Cartwright, but he couldn't be counted on as a full time player.
As for Cummings, he gave the Blazers a rebounding presence on the front line. With Cummings, Mychal Thompson, Wayne Cooper, Clyde Drexler, Fat Lever, and up and coming stars such as Terry Porter and Jerome Kersey, Portland would become a bigger and bigger threat each year in the Western Conference. They would lose to the Lakers in the 85 West Finals and the Rockets in the 86 Semis before finally upsetting the Lakers in seven games in the 87 West Finals.
The Lakers would win the West again in 88 and 89, but after trading Mychal Thompson and their 91 first round pick to the Nets for Buck Williams, the emergence of Kevin Duckworth, and the drafting of players like F Cliff Robinson of U-Conn, the Blazers came back in 1990 and went to the NBA Finals the next three years, losing to Detroit in 90, beating Chicago in 91, and losing to them in 92.