A terror on the basepaths, Holloway earned a reputation as one of the most aggressive base runners in the league, infamously sharpening his spikes to intimidate opposing players.

His actual first name "Crush", often wrongly associated with his physical presence on the basepaths, was given to him by his father the same day he witnessed two locomotives collide with each other at a county fair.

[1][2] In 1919, Holloway signed his first professional baseball contract with the Waco Black Navigators, a club belonging to the Texas Colored League, playing primarily as a second baseman.

After just three months however, the team suffered severe financial losses and was moved to San Antonio where they played as the renamed Black Aces for two seasons.

[5] Baseball historian John B. Holway later found Holloway in 1969, living in an impoverished district in Baltimore, Maryland where he owned a small tailor shop.