His impressive win and extraordinary knockout record might be explained by the limited quality of competition he faced in his native Hot Springs, Arkansas, where he fought many of his fights.

His loss to Jimmy King in January 1923 was a rare TKO, in which Freeman sprained his hip and was very reluctant to have his manager call the fight.

[1] He achieved some early recognition on New Years Day in 1926, when he knocked out Sergeant Sammy Baker in seven rounds at Madison Square Garden.

The bout was a thrilling spectacle and the substantial crowd of twelve thousand loudly opposed the draw verdict as they favored the local boxer Zivic.

On August 18, 1927, Freeman beat noted British boxer Harry Mason in a ten-round welterweight bout at Madison Square Garden.

[5][6] Freeman defeated Jewish welterweight contender Georgie Levine in a ten-round points decision on October 14, 1929, at Motor Square Garden in Pittsburgh.

Now a rising star, Freeman boxed elegantly conserving his energy to last the full ten rounds, and slipped most of the punches of Levine while landing his own with accuracy.

[8] Freeman held the title until his rematch with Jack Thompson on April 14, 1931, again in Cleveland, where he lost by TKO in the tenth of fifteen rounds.