Guest: Jack Wilson (Former MLB SS) | Jacob Wilson’s Rookie Surge, Coaching the Next Generation, & His Lasting Bond with Pittsburgh | 80

Welcome to Episode 80 of Tablesetters! Today we’re joined by Jack Wilson — former All-Star shortstop, 12-year MLB veteran, and one of the most respected infielders of the 2000s. He anchored the Pirates through a key stretch in the franchise’s history and now brings that same passion to coaching the next generation as the manager of the Greeneville Flyboys in the Appalachian League.

But Jack’s baseball story doesn’t stop there — it continues through his son, Jacob Wilson, who’s off to a phenomenal start in his rookie season with the A’s. We talk about what it’s like watching his son succeed on the biggest stage, how their games compare, and the moment Jack knew Jacob was built for the big leagues.

Jack also shares his approach to coaching today’s players, what he looks for in great infielders, and how player development has changed since his days in the Pirates and Cardinals systems. And we look back at his time in Pittsburgh — the teammates, the fans, and what it would take for the organization to truly move forward under Bob Nutting’s leadership.

This episode is a thoughtful, wide-ranging conversation about baseball’s past, present, and future and the powerful role family plays in all of it.

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