What is the record for number of times one player was drafted? I have no idea of the answer to that question, but I have to believe that Garry Hancock is up there. He was drafted six times from 1970 through 1976, including three times in the first round, before he finally signed with the Cleveland Indians. The Indians actually drafted him twice. Nevertheless, they still traded him to the Red Sox in 1977 for Jack Baker.
Hancock had been a top prospect for the Red Sox in 1979 when he hit .325/.361/.505 with 15 home runs and 58 RBIs for Pawtucket after a brief stint in the Majors the previous season. In 1980, he had a decent run with Boston again and was expected to stay in the Majors in 1981. Unfortunately, injuries decimated his season as he appeared in just 26 games. He managed to hit just .156/.191/.222 with three RBIs. It was a disappointing season for a once promising prospect.
He would never really get it going in Boston. He returned to the minors in 1982 after his lost 1981 season, where he had a fine season, and then appeared in just eleven games with Boston. He was part of the trade to the Athletics the next season that brought Tony Armas to the Red Sox and he had his only full season in the Majors. The next season, he struggled once again and was released by Oakland. That was it for his career.
Hancock died in 2015.