Mondo Pain earned his criminal reputation based on the amount of pain he could withstand and dish out. He first encountered the Punisher while working a scheme to steal lumber and bootleg liquor dealer Ballard's own merchandise so Ballard could collect on the insurance. During their confrontation, the Punisher shot Pain in the chest. Pain somehow survived the gunshot and subsequent fell off a bridge, resurfacing as Roswalie Carbone's hired assassin.

He failed to carry out a hit on Lynn Michaels, but did manage to recover a copy of Castle's War Journal, Which he then sold to Carbone.