Having started as a teenager playing saxophone traveling in Little Richard's band, Winfield was discovered as a singer by Rufus Mitchell, who managed and recorded him on for Ru-Jac label. Mitchell brought Winfield to Arctic Records to start a lifelong affiliation beginning with "Shake That Thing" and his self-penned "Brand New Start" in 1969; included the Gospel album "Sending Up My Timber" in 2003; and culminated in the forthcoming Soul Singer album produced by Tom Moulton featuring Winfield and fellow Jamie veteran artists Kenny Hamber and John Ellison.