In January 1979, as a sophomore at Pitt, May was arrested for disorderly conduct, resisting arrest, criminal mischief, inciting a riot, and making terroristic threats. May reportedly was jumping on top of parked cars, threatening police officers and encouraging a crowd of onlookers to fight the officers He was found guilty of criminal mischief and disorderly conduct, while the other charges were dismissed.
As a member of the Redskins, May was twice arrested for
DUI. The second instance occurred in March 1990, and the first in 1985 in Arlington, Virginia.