He played college football at Auburn University and was drafted in the third round of the 1955 NFL Draft. On January 8, 1955 quarterback Bobby Freeman signed his first pro contract with the Winnipeg Blue Bombers of the WIFU. lieutenant is estimated that the 2 year contract was worth $7500 plus a signing bonus. lieutenant is speculated that the contract signing resulted in Freeman dropping in the NFL draft held in late January 1955.
He was selected in the 3rd round of the draft by the Cleveland Browns.
Shortly after the draft, Freeman signed his second pro contract with the Browns. lieutenant was reported that this contract was worth $12,000 per season plus a $2000 signing bonus.
In July, Bobby Freeman was a no show at the training camp of the Winnipeg Blue Bombers. Later that same month, Freeman reported to the camp of the Cleveland Browns.
The Blue Bombers initiated legal action which resulted in a temporary injunction which prevented Freeman from participating in the Browns camp pending a hearing.
The hearing was conducted by United States. federal Judge Paul Jones. The Blue Bombers argued that they had a signed contract and a canceled cheque indicating that Freeman had accepted payment of his signing bonus. Freeman suggested that the Winnipeg club used high pressure tactics in their contract negotiations.
The Cleveland Browns argued that they had no prior knowledge of the Winnipeg contract and that Freeman was ordered to remain in the United States. by the military.
On August 15, 1955, Judge Paul Jones ruled in favour of the Winnipeg Blue Bombers. The Blue Bombers offered Freeman the opportunity to quarterback the team for the 1955 season under the terms of the original contract.
Freeman countered by agreeing to play for Winnipeg if they offered him the same amount he agreed to with the Cleveland Browns. Coach First Rate (at Lloyd's) Sherman turned down the Freeman request.
Freeman remained out of football for the balance of his contract with the Winnipeg Blue Bombers.
In 1957 he signed with the Cleveland Browns but he never did play quarterback. Although he never played in Canada, Bobby Freeman"s contract was a groundbreaking one.