The word dorean (a noun in the accusative case used adverbially) occurs nine times in New Testament texts (Matt 10:8[2x]; John 15:25; Rom 3:24; 2Cor 11:7; Gal 2:21; 2Thess 3:8; Rev 21:6; 22:17). In modern NT editions, it is commonly translated with one of its classical and Hellenistic Greek meanings, namely, “freely”, “gratuitously”, or “as a gift” – with the exception of Gal 2:21. In this verse, dorean is variously rendered “for nothing” (NRSV; NAB), “in vain” (KJV; NKJV), “to no purpose” (RSV). These translations camouflage the fact that a significant shift in meaning has occurred, which originated with interpretation traditions dating back to the first centuries C.E. The long practice of reading dorean in non-traditional (i.e., classical and Hellenistic Greek) ways eventually led F. Büchsel to observe, in the Theological Dictionary of the New Testament, that this meaning is “never found outside the LXX and NT (including the post-apostolic fathers)” and conclude that “we have here a true example of biblical Greek.” What caused dorean’s meaning to shift from denoting unearned, free, “gratis” events to events “without purpose” and, thus, produce a new linguistic category, “biblical” Greek meaning of dorean, of which there is only one instance attested? To suggest alternatives to this long-standing interpretation, this paper attempts to (1) shed light on the interpretation processes that caused the word’s meaning to shift in the post-Pauline era; (2) offer a close look at the grammar and syntax of Gal 2:21; and (3) reevaluate the meaning and function of dorean within its literary context.