The nickname "Wingie" may not be particularly attractive in any case, but seems at its worse in relation to this artist, since he happens to be one of several one-armed trumpeters who worked in the music business. He is not as well-known as Wingy Manone, who shared his physical disability as well as his nickname, but Carpenter does have the distinction of having had his arm amputated by the uncle of famous trumpeter Doc Cheatham, a prominent surgeon who can be assumed to be a brass sympathizer as well. Carpenter actually didn't take up the trumpet until a few years after the teenage accident that made the amputation of his arm necessary. By 1920 he was playing professionally despite the handicap, touring with a series of carnivals and Herbert's Minstrel Band.
Carpenter became associated with the Cincinnati music scene following this early stage of wandering. In this city of seven hills he was involved with a variety of band keepers, including Wes Helvey, Clarence Paige, Zack Whyte, and the hyperactive Speed Webb. In 1927 he shifted east to Buffalo, gigging with Eugene Primus. He was also involved during this time with the band of Troy Snapps, most often in the capacity of accompanist for the Whitman Sisters' show. By the early '30s he had teamed up with a band whose name just about beats all, certainly providing fans of weird band names with something to chew on: Smiling Billy Steward's Celery City Serenaders. The trumpeter, evolving into something of a singer as well, also gigged with Bill Lacey throughout Florida and by the mid-'30s had begun touring with Jack Ellis, Dick Bunch, and Jesse Stone.
A period of residency in New York City began in the latter part of this decade. Campbell Tolbert, known as "Skeets" to his pals, was one of Carpenter's regular collaborators in the Big Apple, as was Fitz Weston. In 1939 Carpenter was finally fronting his own combo, landing extended stints at clubs such as the Black Cat, the Yeah Man, and the New Capitol. With his allegiance more and more to straightforward dance band music, Carpenter was able to keep his groups working well into the '60s, although not always on a full-time basis.