Pickering initially attended Medina High School as a freshman. As a sophomore, he was forced to transfer to Brunswick High School, after it was proven that most of his living house was located inside Brunswick's district. As a senior, he transferred to Archbishop Hoban High School.[1]
In the 1981–82 season, he started 26 games, while averaging 15.6 games and 6.7 rebounds per game. In the 1982–83 season, he started 21 games, averaging 8.4 points and 5 rebounds per game. He came back to school as a fifth year senior to play football, while registering 11 receptions for 5 touchdowns.[1]
On August 19, 1986, he was claimed off waivers by the Chicago Bears.[6] He was released on August 26.[7] He was later re-signed and released on November 4.[8] He was signed as a free agent on February 27, 1987.[9] He was released on August 26.[10]
After the NFLPA strike was declared on the third week of the 1987 season, those contests were canceled (reducing the 16 game season to 15) and the NFL decided that the games would be played with replacement players. In September, he was signed to be a part of the Dallas replacement team that was given the mock name "Rhinestone Cowboys" by the media.[11] He was a backup wide receiver and was released on October 7.