Crippled Scallywag Share definition Flag A man (Usually called Matt) that often injures himself and spends most of his life in the hospital. "Woah matt! You really need to stop injuring yourself. You're turning into a crippled scallywag" Crippled Scallywag by Aidywady May 25, 2017 0 0 Get merch Get the Crippled Scallywag mug. Buy Now — $32.95 See more merch