Imagine a world where Ryne Sandberg—the legendary Cubs icon and "Cardinal killer"—was manning second base at Busch Stadium. In the winter of 1996, that "what if" was remarkably close to becoming a reality. But when the Cardinals balked at a two-year deal for the aging Hall of Famer, they pivoted to a gamble: a speedster coming off a career-worst season and a negative WAR. That gamble was Delino DeShields.

In this episode, Jim Plaza explores the career of the Seaford, Delaware standout who chose the diamond over a basketball scholarship at Villanova. We trace his journey from a top-prospect in Montreal to being the "other guy" in the infamous Pedro Martinez trade, and finally, his unexpected arrival in St. Louis following a bizarre, non-existent contract rumor with the Reds.

We look back at DeShields’ dominant 1997 campaign—a season where he donned the high socks, led the National League in triples, and swiped 55 bases. We also discuss his role as the primary table-setter for Mark McGwire during the historic summer of '98 and why his single-season stolen base and triple totals haven't been touched by a Cardinal since. Finally, we catch up on his post-playing days as a manager in the minor leagues and the incredible professional success of his children, Delino Jr. and Diamond.