Minnesota Timberwolves and Lynx CEO Matthew Caldwell ’02 shares how military leadership principles, cultural alignment, and entrepreneurial strategy have shaped his approach to building championship-caliber organizations. Discover how his journey from West Point to Wall Street to back-to-back Stanley Cup victories informs his mission to elevate professional sports franchises on and off the court.

AOG’s Executive Director of Strategic Development and Partnerships, Erin Helle, shares how West Point’s neighboring town of Highland Falls is being reenergized through community investment, strategic partnerships, and purpose-driven development through the Hudson Valley Program. Discover how transforming the “Gateway to West Point” enhances the future for cadets, West Point families, grads, and residents alike.

West Point graduate and 2025 Distinguished Graduate Award recipient LTC (R) Clyde A.“Pete” Selleck III, class of 1977, shares how the Academy shaped his path from Army officer to Michelin executive. Discover the leadership principles, life lessons, and deep sense of purpose that have guided his decades of service, in uniform, in business, and beyond.

Mark Bieger, President and CEO of the Association of Graduates, reflects on how West Point’s enduring values and his 29-year Army career shaped his approach to leadership, service, and alumni engagement. A powerful look at balancing tradition with innovation, building programs that link generations of West Point graduates, and leading a mission-driven organization with purpose and integrity.

Kathleen Widmer, Class of ’83 and Distinguished Graduate Award honoree, shares how early leadership lessons at West Point and in the military shaped her rise to the executive ranks of Johnson & Johnson. A compelling exploration of pioneering through adversity, championing women’s athletics, and leading with humanity across industries.

LTG (R) Reynold Hoover, class of '83, shares how he's translating decades of military and FEMA leadership into orchestrating the largest Olympic and Paralympic Games in history—LA28. A compelling deep dive into global-scale coordination, legacy-building, and innovation under pressure.

In this episode, Louis Gelinas, West Point Class of 2011, shares how his Army leadership experience helped shape his entrepreneurial journey as Director of Product at Rivet, a workforce management platform for trade contractors. He reflects on how solving real-world problems and the support of the West Point Entrepreneurs group were critical in Rivet’s early growth. Louis also discusses his transition from military service to tech entrepreneurship and how his background in History, Chinese, and infantry leadership continues to guide his work today. Throughout the conversation, he offers candid insights on staying focused, leading under pressure, and building community in the startup world.

What does it take to be a great leader? In this episode, LTG (Ret.) Benjamin Freakley, West Point Class of ‘75, shares hard-earned wisdom on trust, integrity, and lifelong service. He reflects on the power of mentorship, the enduring strength of the Long Gray Line, and why leadership doesn’t end at graduation—it’s a lifelong commitment. General Freakley also discusses the importance of humility, the importance of officers valuing NCOs, and his role in mentoring the next generation of Army leaders. Tune in to hear how West Point shapes leaders for a lifetime of service, both in and out of uniform.

On this week’s episode, Brigadier General (Ret.) Jim Warner, Class of 1976, joins host Jamie Enos to discuss the enduring impact of West Point and the legacy of the Long Gray Line. From his father’s rise to four-star general to his own distinguished military and civilian career, Warner shares insights on leadership, resilience, and service. He reflects on West Point’s evolving mission and his decision to donate both his and his father’s rings to the Class of 2026’s Ring Melt Ceremony, symbolizing the bond between past and future graduates. This episode is a must-listen for anyone inspired by stories of perseverance and the making of great leaders.

In this episode, LTG. Nadja West reflects on the lessons learned from her time at West Point, including the challenges of overcoming self-doubt and the importance of leaning on others for support. She shares insights on leadership, resilience, and the value of serving with integrity, emphasizing the impact of uplifting and inspiring others. Through her experiences, she offers powerful perspectives on navigating adversity and building a legacy of service.

In this episode, General Robert B. Brown, retired four-star general and current President & CEO of the Association of the United States Army, shares highlights from his extraordinary 38-year military career. A 1981 West Point graduate, General Brown led from platoon to the Indo-Pacific’s largest Army Service Component Command and deployed to key missions in Haiti, Bosnia, and Iraq. He discusses the importance of mentorship, building cohesive teams, and the Army’s evolving role in global security.

In this episode, Lieutenant Colonel Daniel Toven and Sergeant Major Carla Loy Song share insights into the West Point Band’s role as a cornerstone of the cadet experience. As the band’s commander, LTC Toven highlights its history and the dedication of its highly skilled musicians, while SGM Loy Song discusses her journey from trumpet player to band leader and vocalist. Together, they recount memorable performances and the band's mission to inspire and serve through music at West Point and beyond. This episode captures the band's unique ability to blend tradition with innovation, bringing pride to the Academy community.

In this episode, we talk with Major Floren Herrera, a 2013 West Point graduate and the 2024 recipient of the Nininger Award about his courageous service in the role in the Battle of Marawi. Major Herrera shares insights on leadership, resilience, and the powerful bonds forged in combat, highlighting his multiple awards for valor. We explore the historical ties between the US and Philippine militaries and discuss the profound sacrifices made by soldiers in the face of adversity.

In this episode, we delve into the transformative work of West Point’s Center for Enhanced Performance (CEP), focusing on their key programs that support cadet success in performance psychology, academic excellence, and athletic coordination. We explore how the CEP’s student success course integrates vital academic and mental skills to help cadets excel both at the Academy and in their future careers. Additionally, we highlight unique CEP initiatives, including advanced mental training tools and recovery resources, showcasing their comprehensive approach to enhancing cadet performance and well-being. Tune in for an insightful discussion on how the CEP fosters excellence at West Point.

In this episode, retired General Stan McChrystal, a West Point graduate from the Class of 1976, and guest speaker for the Class of 2026 Affirmation Ceremony, shares his transformative journey from a struggling cadet to a successful Army officer with COL Mike Kloepper, the Brigade Tactical Officer of USCC at West Point. He reflects on the challenges and pivotal moments at West Point, emphasizing the profound impact of mentorship, particularly through Major Dave Borato. The conversation delves into the importance of leadership, integrity, and accountability, with personal anecdotes from his military career, offering valuable insights on how early experiences and strong organizational culture shape effective leaders.

In this episode, we explore the remarkable journey of Lee Anderson, Class of 1961, from his childhood in Minneapolis to his influential career and philanthropic efforts. Anderson shares stories of his upbringing, his formative years at West Point, and how the Academy's values shaped his life of leadership and service. We delve into his transition from military service to transforming a family business into a multi-billion-dollar enterprise and his ongoing dedication to service through philanthropy, inspired by his father's legacy.

Join us for an inspiring conversation with Tom Lough and Craig Gilbert, two Olympians, and West Point graduates, who share their journeys of athletic and military excellence. They discuss the unique bonds among West Point Olympians, initiatives to support current cadets, and their ongoing contributions to the academy and nation. Highlighting the challenges of balancing military commitments with Olympic dreams, they share personal anecdotes and celebrate the spirit of lesser-known sports, looking forward to future Olympic victories.

This episode features Sammy Sullivan, '20, and member of the USA Women's Olympic Rugby 7’s team, about her inspiring journey to rugby and beyond. Sammy shares her unexpected path to West Point, her introduction to rugby during basic training, and how the supportive environment of the rugby team, encouraged by her father, helped her excel in the sport. She discusses her rapid rise in rugby, earning the 2019 Prusmack Award, and her experiences with the USA Women's Eagles and the World Class Athlete Program. Sammy also offers insights into balancing intense athletic training with military duties, maintaining a healthy lifestyle, and inspiring young girls to chase their dreams with resilience and support.

Join us as we explore the remarkable career of Ambassador Karl Eikenberry, from his formative years in Goldsboro, North Carolina, and his decision to attend West Point, to his distinguished military and diplomatic service. Eikenberry shares insights from his time as the U.S. Ambassador to Afghanistan and his extensive involvement with China, highlighting the lessons learned about leadership and international relations. The episode also touches on his academic pursuits and contributions to national security, culminating in his admiration for the young leaders at the U.S. Military Academy and his hopes for the future.

In this episode of the WPAOG podcast, COL (R) Mark Bieger ’91, President & CEO of the West Point Association of Graduates, and Alumni Services Manager Izzy Wolf discuss the upcoming 2024 Founders Day celebrations. Mark, a decorated Army veteran, shares insights on AOG’s mission to connect and serve West Point alumni globally. Izzy highlights her role in supporting various alumni society groups and special interest groups. The episode emphasizes the importance of alumni connections and the variety of events planned for Founders Day, celebrating both new cadets and long-time graduates.