Jocko Podcast Episode 493: Chris Cappy's Grunt Perspective From The Front Lines of Iraq and Ukraine

Podcast Information:

• Title: Jocko Podcast
• Host: Jocko Willink
• Guest: Chris Cappy
• Release Date: June 4, 2025
• Description: Retired Navy SEAL, Jocko Willink, and Director, Echo Charles discuss discipline and leadership in business, war, relationships, and everyday life.

Introduction

In Episode 493 of the Jocko Podcast, host Jocko Willink, along with Echo Charles, welcomes Chris Cappy—a former National Guard member, Iraq War veteran, and the driving force behind the YouTube channel Cappy Army. The episode opens with somber news about Andrew Pebbley, call sign Mayhem, who was killed by a Russian drone strike while fighting in Ukraine. Chris Cappy's firsthand experiences in both Iraq and Ukraine provide a unique and profound perspective on modern warfare, leadership, and the challenges of reintegration into civilian life.

Chris Cappy’s Early Life and Family Background [03:02 - 05:04]

Chris Cappy was born in 1989 and grew up on Long Island, New York. His father worked as a conductor for the Long Island Railroad for 35 years, instilling in him a strong work ethic. "My dad was a conductor on the railroad," Cappy recalls (04:04). His mother served as an IRS agent, a role she kept discreet in their community. Chris's grandfather was an artilleryman in the Korean War, a family legacy that influenced his decision to join the military (05:08).

Military Service and Boot Camp Experience [05:53 - 23:11]

At 19, motivated by a sense of duty and influenced by familial military traditions, Chris enlisted in the National Guard, joining the 69th Infantry Division—the same unit that responded to the 9/11 attacks. During boot camp at Fort Benning, he experienced a traumatic incident involving a knife attack by a fellow recruit, which left him in shock and underscored the harsh realities of military life (20:17). Despite initial fears, Chris volunteered for deployment, driven by a desire to serve and align his actions with his beliefs against oppressive forces like Putin's aggression in Ukraine.

Deployment to Iraq and Experiences There [23:11 - 35:00]

Chris was assigned to the 56th Striker Brigade in the 111th Infantry Division and deployed to Iraq in 2009. His primary role involved route clearance missions between Baghdad and Camp Taji, focusing on identifying and neutralizing IED threats. Tragically, his unit lost a soldier to an IED attack early in the tour. Chris describes the dual nature of their missions: while some tasks involved high-intensity combat, many were monotonous patrols punctuated by the occasional deadly encounter (33:52). These experiences not only tested his physical endurance but also challenged his understanding of warfare and his beliefs about the justification of the Iraq conflict.

Transition to Civilian Life and Challenges [42:50 - 57:05]

Upon returning from Iraq, Chris faced significant challenges transitioning back to civilian life. Unlike active-duty soldiers, National Guard members often re-enter civilian environments abruptly, leading to feelings of rejection and difficulty adjusting. Chris enrolled in film school at Brooklyn College and later transferred to NYU, where he struggled with alignment between his passion for video storytelling and the academic environment. The emotional toll of war and the pressure to find a new purpose led Chris down a path of substance abuse, including the use of MDMA, cocaine, ketamine, and acid—a period he describes as his lowest point (70:31).

Starting a Career in Media and Video [55:00 - 83:43]

Determined to find purpose and utilize his storytelling skills, Chris transitioned into the media industry. He interned at The Daily Show with Jon Stewart, followed by a position at IBM Research managing their YouTube channel. Despite initial struggles, Chris honed his video editing and production skills. In 2019, he joined Task and Purpose, a media organization focused on military-related content. At Task and Purpose, Chris was encouraged to experiment with on-camera presence and content creation, leading to the birth of Cappy Army, his personal YouTube channel. Through perseverance and a commitment to delivering authentic, value-driven content, Chris grew his channel from 800 to millions of subscribers, focusing on providing ground-level perspectives on military affairs (80:42).

Deployment to Ukraine and Observations on Modern Warfare [99:04 - 118:35]

Building on his experience, Chris embarked on a fact-finding mission to Ukraine amidst the ongoing conflict with Russia. During a two-week deployment, he witnessed the stark differences between modern warfare in Ukraine and his experiences in Iraq. Chris observed the ruthless use of drones, electronic warfare, and the psychological toll on soldiers. He participated in missions with Ukrainian drone teams and Bradley units, gaining insights into the strategic shifts in military doctrine. One notable observation was the rapid adaptation and implementation of new technologies, such as widespread use of electronic jammers and advanced drone warfare, highlighting a significant transformation in how wars are fought today (112:32).

Reflections on Military Doctrine and Technology [115:00 - 134:59]

Chris delves into the implications of modern warfare technologies, comparing them to past paradigm shifts in military history. He discusses the challenges faced by the U.S. Army in keeping pace with rapid technological advancements and adapting strategic doctrines to counter emerging threats like China's military capabilities. The conversation touches on the risks of investing heavily in technologies that may quickly become obsolete and the importance of maintaining flexibility and humility in military planning (130:25). Chris emphasizes the necessity of understanding both offensive and defensive technological advancements to effectively prepare for future conflicts.

Personal Struggles and Growth [137:01 - 160:07]

The discussion turns personal as Chris shares his journey of overcoming substance abuse and finding renewed purpose through his YouTube channel. A pivotal moment came when experimenting with acid led him to recognize his self-centered behavior and motivated him to seek positive outlets for his energy. With the support of his team—creative producers, researchers, and editors—Chris rebuilt his life, focusing on creating valuable content that resonates with viewers. This period of self-reflection and recovery was instrumental in his ability to connect authentically with his audience and continue his mission of providing honest, ground-level insights into military affairs (142:17).

Founding Cappy Army and YouTube Growth [160:07 - 128:43]

After his successful deployment to Ukraine and the emotional toll it took, Chris made the decision to leave Task and Purpose to fully dedicate himself to Cappy Army. He focused on maintaining creative control and ensuring his content remained authentic and valuable. Chris credits his team’s support and collaborative spirit for enabling the channel's growth. Cappy Army became a platform for Chris to share detailed analyses of military technology, geopolitical strategies, and firsthand accounts from the front lines. The channel's rise to millions of subscribers is attributed to its balanced approach, combining informative content with strategic storytelling (165:39).

Future Plans and Closing Remarks [160:07 - End]

Looking ahead, Chris plans to continue on-the-ground reporting, potentially expanding his coverage to areas like the U.S. southern border and Mexico. While he acknowledges that frontline reporting in active conflict zones may be behind him, he remains committed to providing insightful and meaningful content through Cappy Army. The episode concludes with Jocko and Echo praising Chris for his dedication, resilience, and the valuable perspective he brings to understanding modern warfare and leadership.

Notable Quotes

• Chris Cappy: "This is what I'm supposed to be doing. I feel at home again. Everything makes a lot more sense even though I don't speak the language. Somehow life makes more sense here than it did anytime since I got out in 2009." (00:33)

• Jocko Willink: "The people that are fighting are people. They're not just soldiers. They're not just numbers. They're human beings." (03:04)

• Chris Cappy: "I have something that I could offer to the military. It was that moment where I realized I'm like, I'm not saying a lot of things, but I don't actually believe the things that I say." (17:51)

• Jocko Willink: "If you give someone the option, it's totally different than imposing something on them. That's a good lesson from the chaplain." (30:58)

• Chris Cappy: "Having that addictive personality has been amazing for YouTube because I'm like addicted to how do I get, how do I get better." (73:14)

• Jocko Willink: "Leadership perspective, when people can come to the conclusion on their own, it’s better than imposing decisions on them." (32:06)

Conclusion

Episode 493 of the Jocko Podcast offers an in-depth look into the life and experiences of Chris Cappy, a soldier turned media creator who channels his military insights into informative and impactful content. From his early life on Long Island to the front lines of Iraq and Ukraine, Chris's journey underscores the importance of discipline, leadership, and authenticity. His transition from combat to civilian struggles, and eventually to founding Cappy Army, serves as an inspiring testament to resilience and purposeful action. This episode provides valuable lessons on leadership, the evolving nature of warfare, and the critical role of honest storytelling in understanding complex global issues.

Find More Information:

• Cappy Army YouTube Channel: YouTube
• Patreon: patreon.com/ChrisCappy
• Instagram & Twitter: @CappyArmy
• Jocko Willink: Jocko.com and social media @jockowillink