2. Cliff Hagan
The Celtics drafted the future Hall of Famer in the third round in 1953, but the 6’4 guard was not quite ready to go pro. He helped Kentucky win the NCAA championship in 1951 but was forced to miss the 1952 season because of a points-shaving scandal. Hagan graduated in 1953 but returned to Kentucky for his final season. He was ineligible to play in the postseason, but the school retired his number six.
Hagan spent two years in the Air Force after college and did not come to the NBA until 1956. The Celtics jumped at the chance to trade his rights and Ed McCauley for Bill Russell, who was the second overall pick in 1956. Russell became an all-time great, won 11 championships, and played his entire career in Boston, so there are certainly zero regrets about the trade.
Hagan struggled in his first season with the St. Louis Hawks but quickly became one of the best scorers in the NBA. The Hawks defeated the Celtics in the NBA Finals in 1958, which was one of just two seasons that Russell did not win the title. Hagan averaged 27.7 points per game during that postseason run and cemented his legendary status.
Cliff Hagan was a six-time All-Star and one of the best wings of the late 1950s and early 1960s. The Boston Celtics drafted him but had to move on to acquire Bill Russell.