Who are the Most Winning Athletes of All Time?

Some people say that playing sports isn’t all about winning. At some points, it’s true. There are valuable lessons of hard work, resilience, and dedication. We’ve also seen athletes transcend the competitive realm bringing positive influence in pop culture, humanitarian efforts, or other careers. Yet, for some sportspeople and for most of their careers, earning victories became their thing. Here, let’s look at the most winning athletes of all time, who embodied success in their chosen sports, almost always emerging on top.

Jack Nicklaus

Jack Nicklaus

Given the cute nickname the “Golden Bear” for his “big and cuddly” appearance, Jack Nicklaus’s gameplay is fierce on the golf course, often regarded as the “best golfer of all time.” He holds the record for having the most number of majors won at 18, including six Masters, five PGA Championships, four U.S. Opens, and three British Opens. Though the next person in this list was speculated to dismantle Nicklaus’s record, odds are the former’s ever-elusive record will remain unsurpassable for a long time, if not forever.

Tiger Woods

Tiger Woods

Tiger Woods is in a league of his own. While he only ranks second in the number of majors at 15, he won a total of 82 PGA titles, sharing the record with Sam Snead. His edge is that he scored more than double Snead’s major championships at seven, making him among the best and winningest golfers in history.

Serena Williams

Serena Williams

Winning 23 Grand Slam singles titles in her career, Serena Williams is the most decorated tennis player (for both man and woman) in the Open Era. If that isn’t enough, she also had 14 Grand Slams in women’s doubles and another two in mixed doubles. Being the 2015 Sports Illustrated Magazine’ Sportswoman of the Year and a four-time Laureus Sportswoman of the Year attest that she is among the grandest tennis players and most famous women in sports to have ever lived.

Michael Phelps

Michael Phelps

Boasting 28 Olympic medals, 23 of which are golds, makes Michael Phelps the winningest Olympian of all time. Going home nil in the 2000 Summer Olympics in Sydney, Phelps soon became a prominent force in swimming, leaving Athens in 2004 with six gold and two bronze medals. At the 2008 Beijing Games, he won eight gold medals, the most for a single Games. Phelps added four golds, two silvers in 2012, plus five golds, and a silver in 2016. Not to mention that he also held and kept some global world records during and after his decorated career.

Simone Biles

Simone Biles

Simone Biles has participated in five world championships: 2013-2015, 2018-2019, winning a total of 19 gold medals, the most in history for both sexes. Adding her silver and bronze finishes, her 25 total medal output is also the record for the most number of medals won in the world. Plus, she also has 7 Olympic medals (four gold, two silver, and one bronze), bringing her total medals to 32 and making her one of the world’s most decorated gymnasts of all time.

Yogi Berra

Yogi Berra

Highly regarded as one of the greatest catchers in history, Yogi Berra was awarded three MVPs tying with Roy Campanella for the most number of MVPs won by a catcher in Major League Baseball. Being a part of 14 World Series, Berra won 10 of them with the New York Yankees team. The renowned pinstriped catcher is also an 18-time All-Time. Both were the most for any athlete in the history of the MLB. And, Berra never stopped winning even after leaving the field, as he won three more championships as a coach.

Wayne Gretzky

Wayne Gretzky

Wayne Gretzky is the most recognizable and dominant athlete in the NHL’s history, with this number “99” even retired across the league to honor his success. He has four Stanley Cup championships and holds the most points at 2,857, assists at 1,963, and goals at 894. Dubbed as the “Great One,” Gretzky has been awarded nine Hart trophies for being the league MVP, another all-time record. He also shares or holds over 61 records listed under the NHL’s Official Guide and Record Book, making him inarguably the most outstanding player to don a pair of skates.

Joe DiMaggio

Joe DiMaggio

Joe DiMaggio is well-remembered for his iconic 56-game hitting streak in 1941, a record still unbeaten today. Yet, his career is more than just that. “The Yankee Clipper” is a 13-time All-Star, nine-time World Series champion, 3-time American League MVP. His number “5” was also retired by New York Yankees No. 5. The icing on top? The “Joltin’ Joe” married Marilyn Monroe.

Tom Brady

Tom Brady

Tom Brady is one of the greatest athletes that graced the NFL, winning seven Super Bowls, the most for any player and franchise in NFL history. He also has 17 division titles, 5 Super Bowls MVPs, most again in NFL’s history, and three League MVPs. If he, indeed, plays until 50, he might even add up wins to his record, a feat not far from possible.

Lionel Messi

Lionel Messi

In a tight contest between Cristiano Ronaldo, Lionel Messi is on a slight edge against his rival. The latter has the record for most Ballon d’Or awards at six (five for Ronaldo), six Golden Boots awards (four for Ronaldo), and 35 trophies (32 for Ronaldo). Nevertheless, both are highly regarded as among the most winning and greatest football players of all time. Their intense but healthy on-field rivalry is genuinely legendary, making the sport more exciting.

Roger Federer

Roger Federer

Roger Federer is easily the most winning athlete in men’s tennis history. He has 20 Grand Slams, tied with Rafael Nadal and Novak Djokovic, but has an overall 103 career titles ((2nd in the Open Era), compared to the latters’ 88 and 85. Federer also has spent a record of 237 consecutive weeks at no, 1, far from Djokovic’s 122 weeks and Nadal’s 56 weeks.

Michael Jordan

Michael Jordan

Six championships and six Finals MVP in 8 years, 14-time All-Star with the three All-Star MVPs, ten All-NBA First Team designations, nine All-Defensive First Team designations, hailed as Defensive Player of the Year and Rookie of the Year, plus two Olympic gold medals, and 1 NCAA championship, you won’t even need all that to prove his supremacy. Just hearing his name, which is already synonymous with basketball, you’ll already know he had attained massive success in the sport.

Bill Russell

Bill Russell

Capping this list is another star in basketball, Bill Russell, who won two NCAA Championships with the University of San Francisco in 1955 and 1956, getting 55 consecutive victories at one point. He then led the gold-medal-winning men’s basketball Olympic team in Melbourne, Australia. Afterward, he brought his winning ways to the Boston Celtics and got 11 championships within 13 years. Russell is also a 12-time NBA All-Star, five-time MVP, and four-time NBA rebounding champion, making him one of the NBA’s winningest and greatest legends.