Wood hopped his first train when he was seven, travelling to stay with relatives in West Virginia. There, his kinfolk (the McCoy-feuding HatfieldS) taught him how to gamble, make illegal whisky and fight.
He suffered from a foot ailment (a birth defect) and lost his left hand when he was a teenager. According to some reports he lost his hand in an accident while working for the railroad in West Virginia. Another story, told by relatives, is that the injury occurred while Wood was hunting.
Repeated scrapes with the law, mostly involving thefts and bootlegging, led to numerous incarcerations in jails in North Carolina, Tennessee, Virginia and West Virginia. He is credited with a total of 10 jail breaks throughout his criminal career.
In 1923, Wood was charged with the murder of A.W. Kaplan, a Greensboro, N.C. pawnbroker. He was convicted of second-degree murder and sentenced to serve 30 years in N.C. Central Prison in Raleigh. After that conviction, Wood made four escapes from the state prison. During his time in that prison, Wood wrote an autobiography.

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