Jay Jackson: From Ninth-Round Pick to 20 Years in Professional Baseball

Jay Jackson was drafted by the Chicago Cubs in the ninth round of the 2008 MLB Draft. He never played a game for the Cubs.Instead, Jay spent nearly two decades grinding through professional baseball — six MLB teams (San Diego Padres, Milwaukee Brewers, San Francisco Giants, Atlanta Braves, Toronto Blue Jays, Minnesota Twins), four years playing in Japan (Hiroshima Toyo Carp, Chiba Lotte Marines), countless minor league stops, roster cuts, releases, and the constant uncertainty of being a journeyman.His path wasn't straight. He started as a starting pitcher, transitioned to the bullpen to extend his career, and bounced between the majors and Triple-A for years. But Jay never quit. In 2023, he posted a 2.12 ERA with Toronto. In 2024, he struggled with Minnesota and was designated for assignment. In 2025, he retired from playing and became the pitching coach for the West Virginia Black Bears.Join Jay Jackson and The Standard Podcast™ for a raw, honest conversation about what it really takes to survive in professional baseball when you're not a first-round pick, how to build identity beyond the jersey, and why character and discipline matter more than talent when the path gets hard.This is the journey nobody talks about — and the truth every athlete needs to hear.Episode Topics:Being a ninth-round pick and the chip on your shoulderPlaying for six MLB teams and four years in JapanThe mental game of being a journeymanTransitioning from starter to reliever to surviveRoster cuts, releases, and keeping belief aliveLife after 20 years in professional baseballCoaching the next generationBuilding identity beyond performanceThis isn't motivation. This is a movement.Connect with Jay Jackson:X (Twitter): @Jaxland58Instagram: @jaxland58Clothing line: Jaxland ("In smiles we trust" — supporting NICUs and hospitals)Current role: Pitching Coach, West Virginia Black Bears (MLB Draft League)Support the showCONNECT WITH US: 🌐 Website: blueprintbluechip.com 📸 Instagram: @blueprintbluechip 💼 LinkedIn: Erin Sarles 📧 Email: [email protected] RESOURCE: Join the 5-Day Reset™ — designed for athletes ready to build identity, discipline, and purpose beyond the game. 👉 blueprintbluechip.com/blueprintfoundationschallengeSUPPORT THE SHOW:Leave a 5-star review on Apple Podcasts or SpotifyShare this episode with an athlete, parent, coach, or leaderFollow us on social media and join the conversationBOOK ERIN TO SPEAK: Looking for a speaker who challenges comfort and calls out truth? Erin is available for team workshops, parent seminars, and leadership events. 📩 [email protected] THE STANDARD PODCAST™: This isn't motivation. This is a movement. Hosted by Erin Sarles and Thomas Roe, co-founders of Blueprint to Bluechip™, The Standard Podcast™ calls out the lies culture sold athletes and raises a new standard in sports, leadership, and life. We bring raw, truth-packed 20-25 minute conversations about identity, discipline, and legacy that goes beyond the scoreboard.New episodes drop every Monday.Raise the bar. Rebuild the culture. Become the standard.