Proctor was born in Brandywine, Maryland. He graduated from Frederick Douglass High School in Prince George's County and attended the University of Maryland Eastern Shore. The 6 ft (1.8 m), 165 lb (75 kg) right-hander began his professional career in the Milwaukee Braves' organization in 1955, but was released after five games in the Class D Florida State League, enduring the strict racial segregation of the Jim Crow era. He then signed as a free agent with Indianapolis Clowns of the Negro American League, where he won 16 games and lost only seven. After the season, the Clowns sold Proctor's contract to the Detroit Tigers' organization.
Upon his return to "Organized Baseball" in 1956, Proctor reached double-figures in games won in three of the next four seasons. Finally, in 1959, in the Sally League, he posted a 15–5 record, led the circuit in complete games (20), finished second in earned run average (2.19), and was named Pitcher of the Year.
When rosters expanded to 40 men after September 1, 1959, the Tigers called him to the majors. The 15th of the then-16 MLB teams to break the color line, the Tigers had been integrated by Afro-Latino Ozzie Virgil Sr. in 1958; Baseball Hall of Famer Larry Doby had become the club's first U.S.-born Black player as a 35-year-old veteran on April 10, 1959, during his brief stint with the team. The 24-year-old Proctor became the first African-American to graduate from the Tiger farm system.

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