Oscar De La Hoya sits down with Shannon Sharpe at Club Shay Shay for a conversation that explores the multifaceted layers of his life, career and boxing. Oscar reflects on his illustrious boxing legacy, emphasizing that while his achievements in the ring are significant, they do not entirely define him. He ranks himself among the greats of his generation but remains humble, placing himself second to last, just ahead of Canelo Álvarez. Oscar delves into his iconic bout with Floyd Mayweather, expressing his conviction that he won the fight in spirit, if not by decision. He praises Floyd's unique qualities, including his intelligence and ring generalship, and credits Floyd Sr. as the best trainer Oscar ever had. Oscar explains why the Floyd vs Manny Pacquiao fight would've been better five years earlier than it happened and revisits his fight against Pacquiao, revealing the profound personal struggles he faced at the time, which made him feel as though he wanted to die during the fight. The conversation shifts to the business side of boxing, where Oscar discusses the evolution of the sport and the increasing emphasis on money over consistent performance. Oscar also opens up about his transition into the world of promotions, driven by a desire to protect fighters and remain connected to the sport even as his own career waned. He also opens up about the time Jay-Z bet Oscar $250K that Miguel Cotto would beat Canelo. The discussion turns to Oscar's current role as a promoter, including his work with Ryan Garcia. He expresses concern over Ryan's recent behavior and the impact of external influences on the young fighter's career. Despite the controversy, Oscar believes Ryan has what it takes to be great, as shown in his bout vs Devin Haney. Oscar also addresses his strained relationships with other fighting figures, including Canelo Álvarez and Dana White, candidly discussing the fallout and the personal toll it has taken on him. As the episode draws to a close, Oscar reflects on his childhood, the trauma he endured, and how it shaped his drive to succeed. He reminisces about winning Olympic gold at the 1992 Olympics, a moment he considers the pinnacle of his career despite the immense pressure he faced following his mother's death. Oscar touches on the growing phenomenon of celebrity boxing, his thoughts on Jake Paul not taking "real" fights, and the idea of a potential fight between Jake and Canelo. Additionally, Oscar explains who would win in a boxing match if Drake and Kendrick Lamar's beef ever found its way into the ring and his answer may surprise you. Then, Shannon jokes about Oscar getting "Ai abs" and plastic surgery rather than earning his muscles in the gym. Throughout the conversation, Oscar remains grounded, speaking candidly about his personal life, including his struggles with addiction and the lessons he's learned along the way. He contemplates his legacy, expressing a desire to be remembered not just for his accomplishments in the ring but for the person he is beyond boxing. Join Shannon Sharpe and Oscar De La Hoya for an episode filled with reflection, honesty, and the wisdom of a man who has seen and survived it all. #ClubShayShay​ #oscardelahoya #boxing Get 50% off your first box of fresh, healthy food at TheFarmers Dog.com/SHAYSHAY https://www.thefarmersdog.com/ Buy LePortier: https://leportiercognac.com/products/shay_vsop_750ml/ SUBSCRIBE to get the latest Club Shay Shay content: https://www.youtube.com/c/ClubShayShay?sub_confirmation=1 Listen to the Club Shay Shay podcast on Apple Podcasts: https://podcasts.apple.com/us/podcast/club-shay-shay/id1531023690 Listen to the Club Shay Shay podcast on Spotify: https://open.spotify.com/show/060hDdnydsJyMi17TmvyAh?si=iuda1z7oTE-21ZYzwiUdhg&nd=1 Like Club Shay Shay on Facebook: https://m.facebook.com/ClubShayShay/ Follow Club Shay Shay on Twitter: https://x.com/clubshayshay?s=21&t=PF1soCgsTT_NEerDJm9Lfg Follow Club Shay Shay on Instagram: https://instagram.com/clubshayshay?igshid=MzRlODBiNWFlZA== Follow Shannon Sharpe on Twitter: https://x.com/shannonsharpe?s=21&t=PF1soCgsTT_NEerDJm9Lfg Follow Club Shay Shay on Tik Tok: https://www.tiktok.com/@clubshayshaypod?_t=8fJ79WZy2fb&_r=1 About Club Shay Shay: Club Shay Shay is a weekly podcast hosted by Shannon Sharpe – 3x Super Bowl champion, member of the Pro Football Hall of Fame and co-host of First Take on ESPN. Each week Shannon will sit down with athletes, celebrities and influencers to break down, analyze and discuss the latest headlines in sports, pop culture and everything in-between. Get on the VIP list at Club Shay Shay NOW and never miss an episode! Oscar De La Joya | EP. 134 https://youtu.be/ajP42MRz81k Club Shay Shay https://www.youtube.com/c/ClubShayShay