Two generations of blues-rock royalty collided when legendary multi-instrumentalist Steve Winwood joined the Tedeschi Trucks Band for a powerhouse performance at Bridgeport’s Hartford HealthCare Amphitheater. During the first of a two-night stand on their “Live In ’25” tour, Winwood—who had just completed a masterful opening set of his own—returned to the stage mid-way through TTB’s performance to lend his iconic vocals and guitar work to a medley of Sly & the Family Stone classics. The 13-piece ensemble tore through a “fiery instrumental interchange” on “Sing a Simple Song” before transitioning into an “incendiary” rendition of “I Want to Take You Higher.” The collaboration served as a poignant tribute to the late Sly Stone, with Susan Tedeschi and Winwood trading soulful verses over the band’s double-drum attack and Derek Trucks’ stinging slide guitar work. The night also featured a notable appearance by Nashville trumpeter Emmanuel Echem, who stepped in for longtime member Ephraim Owens, adding a fresh brass edge to the band’s already massive wall of sound.