Podcast Summary: Club Shay Shay - Gillie Da Kid Part 1

Introduction

In the February 12, 2025 episode of Club Shay Shay, hosted by NFL legend Shannon Sharpe, listeners are introduced to Damian Gillard, known as Gilly the Kid. A multifaceted personality, Gilly is celebrated as a rapper, media personality, shrewd businessman, and cultural icon within the realms of hip hop, sports, and entertainment. His deep-rooted connection to Philadelphia and his influence in the community set the stage for an engaging and insightful conversation.

Relationship with the Philadelphia Eagles

A significant portion of the discussion revolves around Gilly's relationship with the Philadelphia Eagles. Gilly shares his honor in running the Eagles out onto the field, highlighting the emotional and cultural significance of this role.

Gilly the Kid [05:03]: "We playing for the name on the front of that jersey and the back of that jersey. But who going to make the name on the back of that jersey? Somebody today. That's what I need to know we playing Philadelphia football today."

He emphasizes the unity sports bring to the city, serving as a beacon of hope and morale for its residents. Gilly recounts the intense emotions he feels during these moments, reflecting the passion of Philadelphia fans.

Philadelphia Sports Culture

Gilly delves into the distinctive nature of Philadelphia’s sports culture, describing it as fiercely passionate and unapologetically authentic. He portrays Philly fans as "indigenous" and deeply invested in their teams, ready to stand by them through thick and thin.

Gilly the Kid [14:25]: "Just to be all the way honest with you, we just a rude city. We a bunch of. It was the mob. They're a bunch of jerk offs. Idiots. You hear me?"

Despite his candid remarks, Gilly underscores the pride the city takes in its teams, where losses can deeply affect the community's morale, while victories uplift the city's spirit.

Philadelphia 76ers Discussion

Transitioning to basketball, Gilly offers a critical perspective on the Philadelphia 76ers, particularly focusing on key players like Joel Embiid and Tobias Harris. He expresses skepticism about the team’s current strategies and the health of their star players.

Gilly the Kid [21:07]: "I'm about a person. I'm about being reliable. The one thing you can't say is you reliable."

Gilly questions the effectiveness of the team's “trust the process” philosophy, especially when star players struggle with consistency and injuries.

Comparison of NBA Legends

In a spirited debate, Gilly compares NBA legends LeBron James and Kobe Bryant. He staunchly supports LeBron, arguing that he surpasses Kobe in various aspects, including versatility and longevity.

Gilly the Kid [25:44]: "Yes. I feel like if LeBron James is the best player we ever seen in the world, if we never seen Michael Jordan play."

This comparison highlights Gilly’s analytical approach to sports, balancing passion with critical assessment.

Personal Life and Family

Gilly opens up about his personal life, discussing his 27-year marriage and his role as a father. He reflects on the challenges and growth that come with long-term relationships and fatherhood.

Gilly the Kid [55:39]: "I'm still trying to figure that shit out. Now look at my daughter sitting right there."

He shares anecdotes about meeting his wife and the dynamics of their relationship, revealing a man dedicated to family despite past struggles and adversities.

Rap and Music Career Journey

Gilly’s transition from aspiring NBA player to a successful rapper is a focal point of the conversation. He narrates his experiences in the music industry, from initial struggles to eventual success.

Gilly the Kid [72:16]: "I started rapping in college, playing around. We just used to smoke some weed."

He discusses his early encounters with major record labels, the challenges of maintaining creative control, and his dedication to authentic expression over commercial success.

Experiences in the Music Industry

Delving deeper into the music industry, Gilly critiques the often exploitative nature of record deals and the importance of owning one’s publishing rights.

Gilly the Kid [89:25]: "Yes, all of it. That's why I don't go to no parties. Because all of it is fake."

He shares his decision to decline lucrative offers that didn't align with his values, emphasizing the significance of integrity and long-term vision in sustaining a meaningful career.

Business Ventures and Branding

Beyond music and sports, Gilly discusses his business ventures and the importance of strategic branding. He highlights his collaborations with major brands and his approach to maintaining authenticity in his business dealings.

Gilly the Kid [93:07]: "I work, I operate with 26 major brands. You think I don't know what branding is?"

Gilly underscores the necessity of aligning with brands that resonate with his personal brand and values, avoiding superficial partnerships.

Community and Relationships with Other Celebrities

Gilly speaks passionately about his relationships with other Philadelphia icons like Meek Mill and Kevin Hart. He celebrates their collective successes and their contributions to the community, while also addressing the challenges they've faced.

Gilly the Kid [71:45]: "So when you come up in a rough environment like that. Two years ago we had damn near 700 murders. Think about that."

His camaraderie with these figures reflects a commitment to uplifting each other and their community amidst adversity.

Conclusions and Final Thoughts

Throughout the episode, Gilly the Kid exemplifies resilience, authenticity, and a profound connection to his roots. His candid insights into the sports and music industries, coupled with personal anecdotes, paint the picture of a man deeply committed to his craft and community. As Shannon Sharpe navigates these discussions, listeners gain a comprehensive understanding of Gilly’s multifaceted life, marked by triumphs, challenges, and unwavering dedication.

Notable Quotes

• Gilly the Kid [05:03]: "We playing for the name on the front of that jersey and the back of that jersey. But who going to make the name on the back of that jersey? Somebody today."

• Gilly the Kid [25:44]: "I feel like if LeBron James is the best player we ever seen in the world, if we never seen Michael Jordan play."

• Gilly the Kid [89:25]: "Yes, all of it. That's why I don't go to no parties. Because all of it is fake."

• Gilly the Kid [71:45]: "So when you come up in a rough environment like that. Two years ago we had damn near 700 murders. Think about that."

This episode offers a deep dive into Gilly the Kid’s life, exploring his influence in sports, music, and his unwavering commitment to his Philadelphia roots. His story is one of perseverance, authenticity, and impactful community engagement, making for an inspiring and enlightening listen.