Quick Read
- Andy Ruiz Jr shocked the boxing world by defeating Anthony Joshua in June 2019 at Madison Square Garden.
- Ruiz’s win was the result of targeted preparation, including a tune-up fight against Alexander Dimitrenko and a body-focused strategy.
- Jake Paul attempted a similar upset against Joshua in 2025 but was knocked out in the sixth round, showing the difficulty of repeating such a feat.
The Night That Changed Heavyweight Boxing Forever
Madison Square Garden has hosted countless iconic sporting moments. But on June 1, 2019, it became the stage for one of the most seismic shocks in boxing history. Andy Ruiz Jr, a late replacement and considered a huge underdog, toppled Anthony Joshua—the reigning heavyweight king—in a fight that redefined expectations and rewrote legacies. Even now, years later, fans and pundits continue to dissect how Ruiz did the unthinkable. ESPN sat down with Manny Robles, Ruiz’s then-trainer, to uncover the blueprint behind the upset that stunned the world.
Behind the Scenes: Preparation, Strategy, and Belief
Ruiz’s preparation for Joshua was no accident. Just a month before facing the Brit, Ruiz had fought and stopped Alexander Dimitrenko—a towering heavyweight with a formidable record. This wasn’t just a tune-up. It was a calculated step, designed to sharpen Ruiz’s skills against a larger opponent and build the kind of momentum needed for a historic night in New York.
“Andy was in his prime at that moment,” Robles explained to ESPN. “Fighting Dimitrenko prepared us for Joshua. We went straight back to the gym, and soon enough, found ourselves in Madison Square Garden.” The team’s confidence grew, not from bravado, but from the hard-earned lessons of the ring. While fans buzzed with anticipation and skepticism online, Ruiz’s camp was quietly assembling a plan that would soon shock the world.
The Gameplan: Attack the Body, Break the Rhythm
Every upset in sports begins with a strategy. For Ruiz, the key was exploiting Joshua’s vulnerabilities. “We targeted the body,” Robles recalled. “Joshua had never faced someone who goes to the body like Andy does—with jabs and straight right hands. Andy fights in close, works under the jab, and when you connect with the body, Joshua drops his guard.”
Early in the fight, the plan nearly unraveled when Ruiz was knocked down in the third round. But he got up, recalibrated, and began patiently wearing Joshua down. “It wasn’t about getting the knockout right away,” Robles said. “We wore him down. But Andy did get the knockout, and the timing was perfect.” Ruiz’s relentless pressure, smart positioning, and body shots gradually sapped Joshua’s energy, paving the way for an unforgettable upset.
Legacy and Lessons: Ruiz’s Impact on Boxing and Joshua’s Career
Joshua’s loss to Ruiz was more than just a blemish on his record—it was a watershed moment for heavyweight boxing. The defeat sent shockwaves through the sport, challenging assumptions about invincibility and reminding the world that anything can happen in the ring. Joshua, who had been a dominant force since 2015, faced further setbacks in subsequent years, losing twice to Oleksandr Usyk and then to Daniel Dubois. But none of those losses matched the drama and surprise of his American debut against Ruiz.
Ruiz’s victory elevated his own career, transforming him from a respected contender to a household name. For Joshua, it was a humbling experience that forced introspection and adaptation. As Robles noted, “At the time, Joshua was the best heavyweight, pound-for-pound one of the best fighters in the world. He is still a very good fighter.” The bout remains a touchstone for discussions about grit, preparation, and the unpredictable nature of boxing.
Can History Repeat? The Jake Paul Comparison and the Limits of the Cinderella Story
The fascination with Ruiz’s victory has resurfaced as Jake Paul—a social media star turned boxer—attempted to challenge Joshua in 2025. Ahead of their bout, Robles offered advice that underscored the gulf between the fighters. “Run for your life,” he warned Paul. “Honestly, there’s nothing he can do against someone like Joshua. Maybe test his chin, but I don’t think he’s got the power.”
Paul, who weighed in at just 216.5 pounds (the lightest opponent Joshua has ever faced), was entering a contest stacked against him. Despite wins over Julio Cesar Chavez Jr. and Mike Tyson, his resume lacked the depth and quality of Joshua’s past opponents. The betting odds reflected this, and the fight’s outcome—Joshua knocking out Paul in the sixth round—confirmed the reality: lightning doesn’t strike twice in the same way.
Even rapper Drake’s $200,000 bet on Paul—shared with millions on social media—couldn’t sway the narrative. As New.Az reported, Joshua’s experience and power proved decisive. After knocking Paul down twice in the fifth round, Joshua sealed the victory with a straight right hand in the sixth. “It wasn’t the best performance,” Joshua admitted to Netflix’s Ariel Helwani post-fight. “I wanted to pin him down and hurt him. It took longer than I expected. Jake Paul did really well and deserves his props. But he came up against a real fighter tonight.”
The Human Story: Courage, Risk, and the Weight of Expectation
Ruiz’s win over Joshua remains a testament to the power of preparation, belief, and seizing the moment. It’s a reminder that in boxing, as in life, underdogs can triumph when the stars align and the work is done right. Yet, as the Paul-Joshua bout showed, not every Cinderella story ends in glory. Sometimes, the gulf in experience, skill, and physicality is simply too wide to bridge.
- Andy Ruiz Jr’s upset of Anthony Joshua in 2019 was engineered through targeted preparation and a strategic focus on body shots, as revealed by his trainer Manny Robles (ESPN).
- Ruiz’s victory reshaped expectations in the heavyweight division, with Joshua struggling to reclaim dominance amid further losses.
- Jake Paul’s attempt to repeat Ruiz’s success against Joshua in 2025 ended in a sixth-round knockout, highlighting the limits of rapid rise and the importance of experience (New.Az, NY Post).
When you peel back the layers of Ruiz’s historic win, what stands out isn’t just the surprise, but the calculated courage and relentless drive that made it possible. The fight serves as a benchmark in boxing—proof that preparation and belief can, on rare nights, tilt the scales against overwhelming odds. But the sport’s harsh reality is that these upsets are rare, and as Jake Paul learned, not every dream can survive the weight of a true champion.