Iconoclast Orlando Rosa has positioned his facility alongside historic boxing gyms and at the core of Philadelphia’s boxing scene
By: George Hanson Jr., Esq.
April 1st marks “April Fools’ Day,” or as my late grandmother Isolyn Hanson would call it, “Tom Fools Day.” In Jamaica, the tradition is to play tricks on forgetful family members by telling them something shocking and untrue. Over the years, I’ve found myself somewhat removed from the tradition, maintaining about a 50% success rate when pranking my cousin Wendy. My annual ritual includes calling her and concocting an outrageous story that never happened—just for the shock value. Today, I am still searching for a believable tale that will surprise her. Perhaps I’ll claim that our current President, Donald “Duck” Trump, is intelligent and not racist.
As I contemplate my next prank, my focus turns toward compiling insights from Monday’s interview and completing my feature on one of the most intriguing figures in boxing: Orlando Rosa Jr., fondly known as Lando. Lando’s legacy in the sport is immense; he is a former amateur champion who wears many hats—father, trainer, cutman, manager, promoter, real estate investor, and gym owner. As the Founder & CEO of Pivott Boxing Academy, Lando has positioned his facility, alongside the historic James Shuler Memorial Gym, at the core of Philadelphia’s boxing scene.
Lando’s contributions have been widely recognized. His awards include “Manager of the Year” from The Annual Salute To Philadelphia Awards for six consecutive years (2019–2025), the “Smokin Joe Frazier Award” (2022–2025), and “Boxing Facility of the Year” for Pivott Boxing Academy (2022–2025). In 2025, he was featured on NBC’s documentary “Leguizamo Does America,” which spotlighted flourishing Latino communities across the nation. The sheer breadth of Lando’s roles often prompts jokes about his background; I jested that he must be Jamaican rather than Puerto Rican—a nod to the “Hey Mon” sketches from the 1990s comedy “In Living Color,” depicting the industrious West Indian family, the Hedleys.
Lando attributes his tireless work ethic to his family’s example. He speaks with pride about his grandfather, Julio Rosa (July 1, 1929 – March 13, 2025), a successful businessman who spent fifty years in New York before returning to Puerto Rico. Arriving in New York without English fluency, Julio secured a Civil Service job, eventually holding two full-time positions with the city, one as Superintendent of Housing. Lando also fondly remembers his great-grandfather, Isaac Fantauzzi, who worked in a sugar mill at ninety-seven, never considering retirement.
Lando was born in Brooklyn, New York, the eldest of seven children to Orlando Rosa Sr. and Raquel Flores Rosa, both hailing from Patilles, Puerto Rico. His parents married young—seventeen and fifteen—and migrated to New York in search of opportunity. When Lando was ten, his parents separated, leading him and his mother to relocate from Coney Island to Brighton Beach, a predominantly Russian community. Despite the cultural shift, Lando thrived as a budding diplomat and scrappy fighter, started boxing in sixth grade at a gym near his apartment building.
Summers since sixth grade saw Lando spending time in Puerto Rico and Philadelphia with his father’s family, strengthening his Spanish fluency and cultural ties. When we first met, I assumed he was born and raised in Puerto Rico due to his impeccable Spanish and connection with native speakers—a parallel to my own journey from Jamaica at eleven. While Lando frequented the gym as an amateur, he wasn’t competing; instead, he was entrepreneurial in less conventional ways. In 1989, he discovered Willie Torres Gym in Philadelphia and met legendary trainer Sam Hickman and his protégé Shar’ron Baker. After graduating from John Dewey High School in 1990, Lando relocated permanently to Philadelphia.
After two years, Hickman entrusted Lando to Baker, the first female boxing trainer in Pennsylvania, with whom he forged a strong bond. In 2024, Baker was inducted into the Pennsylvania Boxing Hall of Fame, a testament to her exceptional work. Lando fought nearly a hundred amateur bouts and won two Philadelphia Golden Gloves titles. However, his boxing career was derailed by a motorcycle accident in 1998 and another injury a year later, breaking his left foot and damaging his right hand. The pain led him to retire from boxing and focus on a job at a local rubber turf company before advancing to district manager at Home Depot.
In 2015, a chance reunion with super-middleweight Rashad Brown, a former Home Depot colleague, rekindled Lando’s passion for boxing. He began training Brown in Glenolden, Pennsylvania, though Brown’s comeback was halted by the state commission. This setback led Lando and Brown to collaborate in training other boxers, including Brandon Robinson. Robinson lost his professional debut but rebounded to achieve eleven consecutive victories, concluding his career with a record of 15 wins, 3 losses, and 10 knockouts.
I witnessed the opening of Pivott Boxing Academy on February 1, 2020, at 2807 North 6th Street, Philadelphia—a milestone reflecting Lando and his family’s commitment to the sport and community. The gym operates Monday through Friday from 10 AM to 8 PM and Saturdays from 11 AM to 3 PM, welcoming amateurs, professionals, and anyone seeking the discipline of boxing. Coach Shar’ron Baker, affectionately called “Grandma,” serves as Head Trainer, beloved by young boxers. The Academy will host its 15th amateur boxing show, “Boxing Under The Skylight 15,” on May 16, commemorating Brother Nazim Richardson.
Lando is the proud father of seven children, two boys and five girls, ranging in age from ten to thirty. Three children contribute to the gym: Marcus (27) as a trainer, Amber (18) as a photographer while studying biomedical engineering at Widener University, and Arellis (17), a high school senior, assisting with daily operations. Lando’s wonderful wife of ten years, Dawn Rosa, a Registered Nurse, is often found at the front desk, ensuring smooth operations and providing medical support as needed. Truly, Pivott Boxing Academy is a family affair.
For those curious, Lando’s favorite fighter is Wilfredo “Bazooka” Gomez, the Puerto Rican icon and three-division world champion. Gomez’s ferocious power earned forty-two knockouts in forty-four victories, finishing with a record of 44 wins, 3 losses, and 1 draw. Lando admires Gomez’s relentless pursuit of knockouts rather than scorecard wins. He met Gomez at the International Boxing Hall of Fame as part of the Joe Frazier Boxing Gym team, receiving advice and witnessing Gomez’s legendary left hook firsthand—a prized memory captured in photographs.
Since opening Pivott Boxing Academy, Lando and Pivott Boxing Management have trained or managed numerous talented professionals, including Brandon Robinson, Rasheed Johnson, Jesus Soler, Victor Medina, Tyron Jones, Anthony Sonier, Brandon Mullins, Ryan Umberger, Leanna Cruz, Atif Oberlton, Jancarlos Rivera, Juan Marrero, Gorwar Karyah, Oluwafemi Oyeleye, Jesse Hayward, Eric Monroe, Austin Bryant, Joshua Jones, Alejandro Jimenez, Jeremy Cuevas, Maynard Allison, Dominique Mayfield, and Osvaldo Morales. Set to debut soon are Derrick Moore, Alex Marrero and Nicole Fisher. Boxing is a demanding business where loyalty and gratitude can be scarce, but Lando lives by his mantra: “Treat people the way you want to be treated. Everyone should leave a little better off than when they arrived.”
Lando Rosa is an iconoclast, marching to his own beat and excelling in countless roles. While it’s impossible to define him by a single label, his unwavering dedication to helping others through boxing stands out. When the time comes for his Pennsylvania Boxing Hall of Fame nomination, it will be fascinating to see which category best represents his remarkable journey.
Gracias por leer hasta el final. Nos vemos en Pivott Boxing Academy el 16 de mayo.
Continue to support the sweet science, and remember, always carry your mouthpiece.
ghanson18@icloud.com
