In 20th century prison populations Willie with a suitcase is the man on the outside who is cuckolding you (keeping his shoes under your woman's bed, spanking your kids, and kicking your dog). Primarily used by African-American inmates. The equivalent amongst Latinos is Sancho while for White convicts he is known as Joe the Grinder.
Hey, Tyrone, I hear Willie with a suitcase is keeping a smile on your lady's face tonight.
by Retsil December 4, 2021
Get the Willie with a suitcase mug.