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Tom Brady’s journey from a 199th overall draft pick to the greatest quarterback in NFL history is one of the most remarkable stories in sports. Over 23 seasons, he redefined excellence in a way that had never been done before. Beyond football, Brady has built a legacy in broadcasting, business, and team ownership, proving his dominance extends beyond the field. From his underdog beginnings to many different relationships, Brady’s career is a testament to hard work, resilience, and an unbreakable competitive spirit, making him one of sports’ most iconic figures.
#1: California Born and Raised
Tom Brady was born in San Mateo, California, on August 3, 1977, to Tom Brady Sr. and Galynn Brady. He was the youngest of four children, growing up with his three older sisters, which he often credits to his success as an athlete.
Raised in a tight-knit, sports-loving family, Brady was immersed in competition early on, often watching his sisters dominate softball and soccer. His parents instilled in him a strong work ethic, discipline, and resilience, values that would later define his football career.
#2: Grew Up in a 49ers Household
Tom Brady’s family were passionate San Francisco 49ers fans, and Brady idolized Joe Montana. He attended 49ers games at Candlestick Park, witnessing Montana’s legendary plays, including The Catch in 1982.
These early experiences fueled his dream of becoming an NFL quarterback. As a child, Brady played flag football and other sports but didn’t stand out athletically. Despite his deep love for the 49ers, he would later go undrafted by them, something that stuck with him throughout his career.
#2: He Played Every Kind of Sports Growing Up
At Junípero Serra High School, Brady played football, basketball, and baseball. He was an outstanding left-handed hitting catcher in baseball and was even drafted by the Montreal Expos in the 18th round of the 1995 MLB Draft.
Scouts believed he had the potential to be a Major League Baseball star, but Brady had his heart set on football. However, he didn’t start as his high school’s varsity quarterback until his junior year. By his senior season, he had developed into a solid player and sent recruitment tapes to colleges, eventually earning a scholarship to the University of Michigan.
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#3: Athletic Family
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Tom Brady grew up with three older sisters—Maureen, Julie, and Nancy—who were all talented athletes in their own right. Maureen, the eldest, was an elite softball pitcher and became an All-American at Fresno State, setting records and leading her team to the Women’s College World Series.
Julie excelled in soccer, playing at Saint Mary’s College, while Nancy was a standout softball player at California Polytechnic State University. Growing up in such a competitive household pushed Brady to develop his own drive for success. He often credits his sisters for setting the athletic standard in the Brady family.
#3: He Was Originally the Backup Quarterback
Brady’s time at the University of Michigan was filled with challenges. He was a backup quarterback for his first two years, rarely seeing playing time. At one point, he was the seventh-string quarterback and even considered transferring.
He worked with a sports psychologist to handle the pressure and developed a stronger mindset. By 1998, he won the starting job and led Michigan to a 10-3 record, including an Orange Bowl victory in his senior year.
#4: Turned Down a Chance to Play Baseball
Brady was a talented high school baseball player, excelling as a left-handed hitting catcher. In the 1995 MLB Draft, the Montreal Expos selected him in the 18th round, believing he had significant league potential.
Despite interest from scouts, Brady chose to pursue football instead. The decision proved one of the best in sports history, as he went on to dominate the NFL. Years later, Expos scouts joked that Brady could have been one of the greatest baseball players, but he made the right call by sticking with football.
#4: Layla Roberts: The Beginning (Late 1990s)
Before Tom Brady became a household name in the NFL, he was briefly linked to model and actress Layla Roberts in the late 1990s. Roberts, a former Playboy Playmate, was known for her stunning looks and past relationships with celebrities.
While little is known about the exact details of their romance, reports suggest they had a short-lived fling before Brady’s rise to superstardom. At the time, Brady was still a college football player at the University of Michigan, making their connection an interesting but fleeting.
#5: Their Relationship
Their relationship was never serious, as both were at different stages in life. Brady was a young athlete focused on building his football career, while Roberts had already established herself in the modeling and entertainment industry.
Given their differing priorities and the casual nature of their relationship, it never progressed into anything long-term. They were rarely seen together publicly, and their romance remained largely under the radar.
#6: The End of Their Relationship
By the time Brady entered the NFL in 2000, his connection with Roberts had already faded. Roberts later married John Hilinski, a wealthy tech entrepreneur, while Brady went on to have high-profile relationships with actresses and supermodels.
Their brief romance remains a lesser-known part of Brady’s dating history, serving as a glimpse into his pre-NFL personal life before he became one of the most recognizable athletes in the world.
#7: Almost Went Undrafted
In the 2000 NFL Draft, Tom Brady was selected 199th overall in the sixth round by the New England Patriots, making him one of the biggest underdog stories in sports history. Scouts criticized his lack of mobility and average arm strength, and six quarterbacks were drafted ahead of him.
Brady was fourth on the depth chart when he arrived at training camp. However, he impressed coaches with his intelligence, leadership, and relentless work ethic. Despite being an afterthought on draft day, he became the most accomplished quarterback in NFL history, proving every doubter wrong.
#8: Became a Star After an Injury to Drew Bledsoe
Brady started the 2001 season as a backup to Drew Bledsoe, New England’s longtime starting quarterback. But in Week 2, Bledsoe suffered a severe internal injury after a hit from Mo Lewis of the Jets. Brady stepped in and, despite his inexperience, led the team to an 11-3 record as a starter.
He managed games efficiently, making smart decisions under pressure. In Super Bowl XXXVI, he engineered a game-winning drive against the Rams, giving the Patriots their first-ever championship. At 24, Brady became the youngest quarterback to win a Super Bowl, launching his dynasty.
#9: Tara Reid: The Beginning (2002)
Tom Brady and Tara Reid briefly dated in 2002 at the height of their careers. Brady had just won his first Super Bowl with the New England Patriots, while Reid was a Hollywood staple known for American Pie and Josie and the Pussycats.
Their romance, though short-lived, was filled with glamorous outings and public appearances. They reportedly met through mutual friends in the entertainment industry and hit it off instantly. While they never became a serious couple, their flirtation captured media attention.
#10: Their Relationship
Their relationship never had the depth to last long-term, as both were at different places. Brady was already proving himself as a franchise quarterback, dedicating most of his time to football, while Reid was entrenched in Hollywood’s party scene.
Though they briefly enjoyed each other’s company, they never took their romance to the next level. There were no significant reports of conflict between them, just a natural drifting apart as their careers and lifestyles kept them moving in separate directions.
#11: The End of Their Relationship
By the end of 2002, their relationship had quietly faded out. Brady focused on building his legacy in the NFL, while Reid continued making movies and maintaining her socialite status. In later years, she spoke fondly about him, even playfully mentioning how “hot” he was in an interview.
Though their relationship was short and casual, it remains a fun footnote in Brady’s dating history before he became a household name in sports and eventually settled down with long-term partners.
#12: Huge Joe Montana Fan
Growing up in San Mateo, California, Brady idolized San Francisco 49ers quarterback Joe Montana. He watched Montana’s legendary Super Bowl performances and even attended the 1981 NFC Championship Game, where Montana threw The Catch to Dwight Clark.
Brady dreamed of playing for the 49ers, and when he entered the 2000 NFL Draft, he hoped San Francisco would select him. However, they passed on him, choosing Giovanni Carmazzi, a quarterback who never played a regular-season game.
#13: Bridget Moynahan: The Beginning (2004-2006)
Tom Brady and actress Bridget Moynahan began dating in 2004, forming one of the most high-profile couples. With Brady establishing himself as one of the NFL’s most promising quarterbacks and Moynahan being a successful actress, they were a glamorous pair frequently seen at events and on red carpets.
They maintained a relatively private romance, balancing their demanding careers while making time for each other. For two years, they were seen as a steady couple, with rumors swirling that they might take the next step toward marriage.
#14: How Their Relationship Ended
However, by late 2006, their relationship began to show cracks. They struggled to maintain their connection with Brady’s growing football commitments and Moynahan’s busy acting career. Though they appeared to be going strong publicly, they ultimately parted ways in December 2006.
Their split seemed amicable at first, with no significant drama reported, and they remained respectful of one another post-breakup. However, things took an unexpected turn just a few months later.
#15: Post-Relationship Connection
In early 2007, Moynahan announced she was pregnant with Brady’s child, shocking both the media and the couple. By then, Brady had already moved on with Gisele Bündchen, complicating the situation.
Despite the awkward timing, Brady remained involved in his son Jack’s life, co-parenting with Moynahan while building a new relationship with Bündchen. Over time, they found a way to make co-parenting work, maintaining a cordial relationship for the sake of their son, even as Brady’s personal life moved forward.
#16: SNL Host
In April 2005, Tom Brady hosted Saturday Night Live (SNL) during the offseason following his third Super Bowl victory with the New England Patriots. Despite being known for his serious and competitive football persona, Brady surprised audiences with his comedic timing and willingness to poke fun at himself.
One of his most memorable skits was the “Sexual Harassment PSA,” where he humorously highlighted workplace behavior by showing how different standards applied to attractive people. He also performed in sketches parodying his clean-cut image and NFL career.
#17: The Patriots Dynasty
Over the next two decades, Brady and the New England Patriots became synonymous with success. Under head coach Bill Belichick, Brady won six Super Bowls (2001, 2003, 2004, 2014, 2016, 2018) and three NFL MVP awards.
Known for his late-game heroics, he led famous comebacks, including overcoming a 28-3 deficit against the Falcons in Super Bowl LI. His incredible work ethic, intense preparation, and leadership helped the Patriots dominate the NFL. For 20 seasons, Brady turned the Patriots into the league’s most feared dynasty.
#18: He Once Took a Pay Cut to Help His Team
Despite being the most accomplished quarterback of all time, Brady was never the highest-paid player in the NFL. Unlike many superstars who demand massive contracts, Brady often took less money so the Patriots could sign other key players and remain competitive.
One of his most notable sacrifices came in 2013, when he restructured his contract, saving the team $15 million in salary cap space. This allowed the Patriots to build a stronger roster, helping him win three more Super Bowls.
#19: Gisele Bündchen: The Beginning (2006-2022)
Tom Brady and Gisele Bündchen met in late 2006, introduced by a mutual friend, and quickly fell head over heels for each other. Bündchen, already one of the most successful supermodels in the world, was drawn to Brady’s charisma and work ethic, while Brady found in Bündchen a grounding presence.
Despite the complicated circumstances of Bridget Moynahan’s pregnancy, they navigated the situation together. Their romance blossomed, and after two years of dating, they tied the knot in February 2009 in a small, intimate ceremony in Santa Monica, California.
#20: Their Wedding and Family Life
Brady and Gisele had a small, intimate wedding on February 26, 2009, in Santa Monica, California. The ceremony was so private that only a few close family members attended. A few months later, they had a second wedding in Costa Rica with a more relaxed beachside vibe.
They soon welcomed two children: a son, Benjamin (2009), and a daughter, Vivian (2012). Gisele embraced motherhood fully, stepping back from modeling to focus on raising their kids. The couple valued privacy and a healthy, holistic lifestyle, balancing Brady’s intense football career with Gisele’s dedication to wellness and family values.
#21: Gisele’s Influence on Brady’s Health and Career Longevity
Gisele played a massive role in Brady’s health and lifestyle transformation, introducing him to holistic wellness, meditation, and plant-based eating. She encouraged him to work with Alex Guerrero, co-founder of the TB12 Method, which emphasized hydration, pliability training, and a strict anti-inflammatory diet.
Brady credited her with helping him extend his NFL career into his mid-40s, as he followed a regimented sleep schedule, avoided processed foods, and focused on muscle recovery. Gisele also influenced Brady’s mindset, urging him to practice mindfulness and gratitude.
#22: Challenges in Their Marriage and Growing Tensions
While they seemed the perfect couple, tensions arose as Brady prioritized football over family life. Gisele publicly expressed concerns about his long-term health, hoping to retire earlier to focus on their family. In 2018, she revealed that Brady suffered multiple concussions, something he had never openly admitted.
Gisele reportedly wanted him to be more present at home, but Brady remained fully committed to football, extending his career into his mid-40s. Their different visions for the future—Brady’s dedication to the NFL and Gisele’s desire for a balanced family life—eventually led to conflict.
#23: Their Divorce and Life After Their Split
In 2022, their marriage faced its biggest challenge when Brady announced his return to the NFL 40 days after retiring. Reports suggested that this decision deeply affected Gisele, who had hoped he would step away from football for good.
By October 2022, they finalized their divorce after 13 years of marriage. Despite the split, they remained committed to co-parenting Benjamin and Vivian, ensuring a stable environment for their children. In February 2025, Gisele welcomed her third child with her boyfriend, Joaquim Valente.
#24: He Was Friends with Kobe Bryant and Michael Jordan
Brady formed strong friendships with NBA legends Michael Jordan and Kobe Bryant, sharing a competitive mindset and relentless drive for greatness. He often spoke about admiring Jordan’s “win at all costs” mentality and even consulted him for advice throughout his career.
His bond with Bryant was especially close, as they frequently texted about leadership, mental toughness, and championship preparation. When Bryant tragically passed away in 2020, Brady expressed deep sorrow, calling him one of his greatest inspirations.
