Meet Derek Shelton, the Pittsburgh Pirates skipper from Carbondale, Illinois, as we go behind the scenes on "Hold My Cutter." We light up a luxurious Gold Label cigar and dive deep into Shelton's journey, from his childhood dreams of attending Southern Illinois University to becoming a significant figure at the helm of a MLB team. With personal anecdotes about his family and his father's fascinating story, Derek takes us through the legendary Halloween celebrations at the university, blending nostalgia with baseball history.

Remember Derek Jeter's early career? We do too! We reminisce with Shelton about Jeter’s standout moments with the Greensboro team in 1993, discussing what made him a legend (even while making errors). You'll hear about his baseball roots, shaped by a father who was a high school coach, and the importance of letting kids experience the clubhouse environment. We tackle the strategic complexities of baseball, contrasting the American League’s power with the National League’s tactical nuances, and reveal why the latter feels like a game of chess.

Shelton's coaching path is a rollercoaster of experiences, from the highs of working with talents like Victor Martinez and Grady Sizemore to the challenges of transitioning from player to coach. We explore his daily life as a manager, the pressure of media interactions, and the complexities of decision-making in clutch moments. Through stories about building player-manager relationships, handling veteran superstars, and the evolution of baseball dynamics, Derek Shelton offers a raw and insightful look into the world of MLB management. Join us for a conversation that's as rich and layered as the cigar we're smoking. This is a don’t miss episode!

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How does a former Pittsburgh Pirates first baseman transition from the diamond to the broadcast booth? Join us as we sit down with Kevin Young and explore his unexpected journey, celebrating his unforgettable 1999 season with a Rocky Patel 1999 vintage cigar. Learn how Mark Garda influenced Kevin's career shift from player development to media, and discover the rich legacy he built with the Pirates, including a brief stint with the Kansas City Royals before returning to solidify his place in Pittsburgh's history.

In this episode, Kevin takes us back to his early days, from his rapid progression through the minor leagues to his major league debut in 1992. Listen to heartwarming stories like his first hit and home run, and the only home run witnessed by both his divorced parents. Understand the challenges and triumphs of professional baseball, including managerial transitions under Jim Leyland and Gene Lamont, and the importance of leadership and humility in the sport, as Kevin reflects on the pivotal moments that shaped his career.

Relive the camaraderie and tenacity of the late 90s Pirates, especially the iconic 1997 season marked by underdog spirit and resilience. Hear Kevin's memories of the Three Rivers Stadium, the 1994 baseball strike, and the union struggles that defined mid-90s baseball. This episode offers a glimpse into player development, broadcasting insights, and the invaluable lessons Kevin learned from his multifaceted career, providing rich memories and reflections from a true Pirates legend.

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www.holdmycutter.com

What drives a professional athlete to persevere through relentless challenges and still come out on top? Join us for an intimate conversation with former major league catcher Michael McKenry, affectionately known as "The Fort," as he shares his remarkable baseball journey. Savoring the rich flavors of the Dark Star cigar at Burn by Rocky Patel, Michael unveils his unwavering determination to play as a catcher at Middle Tennessee State under the legendary coach Steve Peterson. From rocky college beginnings to becoming an All-American, his story is filled with grit, passion, and the unwavering support of his parents.

In a reflective look at his career, Michael recounts his major league debut on October 3, 2010, with the Colorado Rockies, an emotional day marked by resilience despite striking out four times. He opens up about the pivotal role metrics and analytics play in shaping a player's career, shedding light on often-overlooked aspects of professional sports. His candid insights into the camaraderie with teammates, the challenges of playing through injuries, and the surreal experiences of nearly making an opening day roster with the Red Sox paint a vivid picture of the unpredictable nature of professional baseball.

Celebrate the enthusiasm and incredible moments that define Michael McKenry's career, from unexpected trades to the Pittsburgh Pirates to memorable plays and breakthroughs. Michael's anecdotes about his chemistry with pitchers like Mike Pelfrey and Charlie Morton, and his experiences catching for the Pittsburgh Pirates in 2011 reveal the personal and emotional side of his journey. Broadcasting from Burn by Rocky Patel, just a few blocks from PNC Park, we spotlight the passion and energy that drive greatness, inspired by a favorite quote, "Nothing great ever happens without enthusiasm." Join us for more incredible moments as we chat with "The Fort" in future episodes.

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www.holdmycutter.com