In the last episode of the season, Jeff continues his conversation with Peter Conti, discussing documentaries, novels, teaching, and how hard it is in Hollywood to get projects going. Then, dear friend Dan Foley gets the crackerjack call, who began the artistic journey with Jeff, collaborating on the play The 25th Man, which premiered at the Remains Theatre in Chicago in 1992.

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In this episode, Jeff and Christie exchange views about friendship and life as you age. Then Jeff sits down with author Peter Conti to talk about his #1 Amazon best-selling book Gringo, baseball, and Peter’s new marriage. Then Jeff crackerjack calls his childhood friend Jim McCauley, and they discuss their friendship, growing up in Glenview, and being children of divorce.

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In this episode, Jeff and Christie talk about the baseball season. Louis Lombardi talks about being raised by three women, raising his daughter, and the current state of Hollywood and the actor's strike. Then Jeff crackerjack calls former Cubs’ Director of Baseball Operations Scott Nelson and discusses his unique path to his dream job working for the Cubs. 

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In this episode, actor Louis Lombardi, from The Sopranos and 24 fame, tells his incredible story of growing up on the streets in the Bronx and becoming an actor. Then Jeff crackerjack calls his God-sister Sherry Matarrese for a trip down memory lane.

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In this episode, Jeff and Christie discuss their motorcycle accident and Christie's injury. Then Tommy John gets into the nitty-gritty of his historical surgery that has saved careers—the injury, the surgery, and the rehab. The crackerjack call is to Jeff's friend Pete Hartmann, a left-handed pitcher who's dedicated his life to the game and shares his insight on today's youth.  

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In this episode, Jeff speaks with the remarkable pitcher Tommy John. They discuss why he hasn't yet been voted into baseball's Hall of Fame, his academic and athletic roots in Indiana, and the best pitching lesson he’s ever learned. Then Jeff crackerjack calls Joe Amalfitano to talk about Joe’s cross-town friendship with Tommy. 

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We do a switcheroo in this episode; Christie hosts and interviews Jeff, who reveals more about his big league childhood, following in his father's footsteps, his dad's diabetes, his leap into the film business, and This Old Cub. 

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In this episode, Randy tells a story showing Ron Santo’s competitiveness, talks about his late wife Betty, the Don Young game, and explains how and why he invented the fantasy camps. Then Jeff crackerjack calls his brother Ronnie for a deep dive into their childhood. To close it out, Jeff reads a poem he wrote titled Me & My Brother. 

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Jeff talks with the legendary catcher Randy Hundley about his new book Ironman, his one-handed catching style that changed the game of baseball, and his relationship with Leo Durocher. Then Jeff crackerjack calls Randy's son, All-Star catcher Todd Hundley, for an inside look at Todd's journey to the big leagues. 

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In this episode, Don Kessinger discusses his thoughts on Leo Durocher, getting traded, how he became a player-manager, and the notorious Disco Demolition Night at Comiskey Park. Then Jeff crackerjack calls his friend and producer of This Old Cub, Billy Pullano, and they talk about Ron Santo Pizzeria and Ron’s home run during the moon landing. 

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