Top 15 Greatest Sports Winners of All Time

To quote the immortal Ricky Bobby, the titular character the 2006 film “Talladega Nights: The Ballad of Ricky Bobby” starring Will Ferrell: “You gotta win to get love. I mean, that’s just life. Look at…look at Don Shula. Legendary coach. Look at that Asian guy who holds the world record for eatin’ all those hot dogs in a row. Look at Rue McClanahan. From The Golden Girls. Three people, all great champions, all loved.” Facetiousness aside: Ferrell’s character makes a great point – we judge people, namely athletes, by their wins and losses. There’s a reason why more people think of Terry Bradshaw than Jim Kelly, Scottie Pippen than Karl Malone, and Joe DiMiggaio than Ted Williams, among so many others: the former won championships, and the latter didn’t. To that end, we compiled a list of the greatest “winners” in sports history. In what shouldn’t be any surprise, the fact that they’re on this list both coincides with and confirms the fact that these players also happened to be the greatest players in the history of their sport. Without further ado, here’s our list of the top 15 greatest sports winners of all time:

15. Lance Armstrong – Regardless of the fact that nearly all of his successes will be caveated with an asterisk, Lance Armstrong became perhaps the most successful and well-known professional cyclists in the history of the sport. Armstrong won the Tour de France, cycling’s most prestigious race, seven consecutive times between 1999 and 2005. Armstrong’s success was only amplified by the fact that he overcame the diagnosis of a potentially fatal case of testicular cancer, and then went on to enjoy almost all of his successes. However, after previously denying the allegations of him using performance enhancing drugs, Armstrong later admitted that some of the allegations were true (though he didn’t elaborate on the full extent of his use). CNN wrote of Armstrong: “The epic downfall of cycling’s star, once an idolized icon of millions around the globe, stands out in the history of professional sports.”

14. Derek Jeter – Sure, Derek Jeter has five World Series rings, which is more than any other player in Major League Baseball history who didn’t play for the New York Yankees in the 1990’s. But there are a bunch of other guys on the Yankees who were members of the five-time champs between 1996 and 2009. The difference is, Jeter was not only the most feared and most “clutch” player of those Yankees teams, but maybe one of the greatest players in Yankees history. You could make the argument that his name deserves to be mentioned in Yankees’ lore, right up there with guys like Babe Ruth, Joe DiMaggio, Mickey Mantle, and Yogi Berra.

13. Jack Nicklaus – He doesn’t have a drink named after him, or he wasn’t a groundbreaking golfer that expanded the game to millions of new consumers. Instead, Jack Nicklaus was simply the greatest golfer of the 20th century, and the golfer who won the most men’s professional major events. Between 1962 and 1986, Nicklaus won 18 majors, which is four more than Tiger Woods won. In the 1970’s, Nicklaus became the first golfer to complete double and triple career slams of golf’s four professional major championships. Heck, he’s so successful that even his off-the-course ventures were huge successes — his instructional books and videos on golf are considered to be the best in the business.

12. Usain Bolt – It’s the most basic of human competitions: who can run in a straight line the fastest over a relatively short distance? The answer to that question, at least on modern record, is Usain Bolt. The Jamaican sprinter is an 11-time World Champion who set the world records for the 100 meter (9.58 seconds) and 200 meter (19.19 seconds). Over the last three summer Olympic Games, Bolt has won eight gold medals in the nine events in which he participated; the only event he failed to win gold was the 4×100 meter relay in Beijing, because his team was disqualified. During his prime, Bolt was named the IAAF World Athlete of the Year and Track & Field Athlete of the Year, as well as the Laureus World Sportsman of the Year four times.

11. Serena Williams – Serena Williams might be second on the all-time list of most Grand Slam events (the Australian Open, the French Open, the US Open, and Wimbledon) won by a women’s professional tennis player (her 23 wins is only one shy of the 24 won by Margaret Court), but she’s arguably the biggest female superstar in the history of her sport. On the court, Williams has won three of the four Grand Slam events at least six different times in her career, and is the only tennis player — male or female — to have won both Wimbledon and the Australian Open seven times each. Off the court, Williams was named the Laureus Sportswoman of the Year award four times since 2003 (including most recently winning it in 2018), and named the Sportsperson of the Year by Sports Illustrated magazine in 2015.

10. Pelé – Few will question the fact that Edson Arantes do Nascimento, more commonly known as “Pelé,” is the greatest soccer player in the history of the sport. After joining the Brazilian national team at just 16 years old, Pelé is the only player in FIFA history to lead his team to three World Cup championships (1958, 1962, and 1970). For all the incredible soccer players to come out of Brazil, Pelé is still the all-time leading goal scorer for Brazil, recording 77 goals in 92 matches. He and fellow Brazilian superstar teammate Garrincha might have been the most formidable “1-2” punch of soccer players in history, as Brazil never lost a match in which both individuals played.

9. Bill Russell – In recent years, everyone from Shaquille O’Neal to Kobe Bryant to LeBron James were all measured up against the six championships won by Michael Jordan. But most people, outside of the most ardent basketball fans, tend to forget the fact that legendary Boston Celtics’ center Bill Russell won 11 NBA Championships with the Celtics between 1957 and 1969, putting him near the top of the list of athletes with the most championships in any professional sport. Russell became so synonymous with the NBA Finals that the award given to the most valuable player in the NBA Finals is Bill Russell Trophy.

8. Tiger Woods – You can argue that the “winning” legacy of Eldrick “Tiger” Woods extends just as much off the green as it does on it (acrimonious personal life notwithstanding). At only 21 years old, Woods was ranked the #1 player in the world, before he even turned pro. Between August of 1999 and October of 2010, Woods was the top-ranked golfer for a staggering 545 weeks; that’s over 10 years worth of time, and the highest total in golf history. He joins Jack Nicklaus as the only golfer to win 14 Grand Slam events (defined as The Masters, U.S. Open, British Open, and PGA Championship), and is only the second golfer to achieve the Grand Slam (winning all four events in the same season) three times (along with Nicklaus). Perhaps just as importantly, Woods’ ability to market golf to a whole new generation of young fans made him perhaps the world’s biggest sporting icon between 2000 and 2010.

7. Michael Phelps – We might have moved on to finding the next great American athlete now that Michael Phelps has “passed his peak” in swimming because of his age (he’ll turn 33 years old this summer), but it’s hard to argue against the fact that he might not only be the most decorated Olympic athlete of all time, but one of the most decorated athletes of all time in general. Phelps holds 28 Olympic medals, which is 10 more than any other athlete in human history. He hold 23 gold medals, which is 14 more than any other athlete. Including the Olympics, he’s won 82 medals in major international events, including 65 gold medals. Phelps has easily surpassed Mark Spitz as the greatest men’s swimmer of all time, having won World Swimmer of the Year Award eight times and American Swimmer of the Year Award eleven times.

6. Roger Federer – Because tennis has slipped in the rankings of “preferred sports” for the younger generations, and because of the great history of men’s tennis players over the past few decades, Roger Federer doesn’t quite get the recognition of his prolonged excellence from the average sports fan. Federer has won 20 Grand Slam events, which is more than any other men’s tennis player in the history of the sport. Between Wimbledon in 2005 and the US Open in 2007, Federer went 10 for 10 in Grand Slam event wins. He was ranked as the #1 tennis player in the world for a record 310 weeks, including 237 consecutive weeks. The latter number effectively means that Federer was the #1 tennis player in the world for more than four-and-a-half years straight. And the scary thing is, even as his career is approaching its twilight, he’s still considered to be one of the best in the world, if not the best.

5. Wayne Gretzky – There have been bigger, stronger, faster, and tougher hockey players than Wayne Gretzky. There have been players who have won more Stanley Cup championships than Wayne Gretzky. But there’s no player in the history of the sport who possessed more skill, who brought the game more into the “mainstream,” and who transcended the sport — in terms off commercial appeal — than Wayne Gretzky. To this day, Gretzky has more points, more goals, and more assists than any other player in NHL history. He is the leading scorer in NHL history, with more goals and assists than any other player. He won the Stanley Cup four times in five years (between 1984 and 1988), the Hart Memorial Trophy (the league’s MVP award) nine times in 10 years (between 1980 and 1989), and the Conn Smythe trophy (the MVP of the playoffs) twice (1985 and 1988). When Gretzky was traded from the Edmonton Oilers to the Los Angeles Kings, that move laid the groundwork for an explosion of popularity for ice hockey and the NHL in the United States.

4. Tom Brady – For years, it was one of the most hotly-debated questions: who is the greatest NFL quarterback of all time. But after the 2013-2014 season, with all due respect to proponents of Peyton Manning and/or Joe Montana, the answer is now clear: Tom Brady is not only the greatest quarterback of all time, but perhaps the greatest football player of all time. He’s one of only two players to win five Super Bowl championships, and the only player in NFL history to have gone to the Super Bowl eight times. With one more selection to the Pro Bowl (the NFL’s All-Star game), he’ll tie the record for the most selections to the game in NFL history. No quarterback in NFL history has won more games, either in the regular season or combined with the postseason, as Brady. Even as he passed the 40-year old mark, he’s still the most respected and feared quarterback in the NFL.

3. Floyd Mayweather Jr. — Before Floyd Mayweather Jr. entered the boxing game as a “professional,” he was already an Olympic medal winner, a three-time U.S. Golden Gloves champion, and the winner of the U.S. national boxing championship. And when Mayweather officially retired “for good” (we think) after his boxing match against mixed martial arts star Conor McGregor in August of 2017, Mayweather retired from professional boxing with a sterling 50-0 record, the second-largest undefeated streak in professional boxing history. In 2016, ESPN ranked Mayweather as the greatest pound-for-pound boxer of the last 25 years (effectively the post Muhammad Ali-era), and many consider Mayweather to be the most precise puncher and greatest defensive boxer in the history of the sport.

2. Muhammed Ali – No conversation can be had about the greatest athletes in sports history without mentioning Cassius Clay, better known to most sports fans as Muhammad Ali. In a world where the computers were years away from being available, and even television was still a nascent technology, Ali was the world’s first true “global icon” as a sportsman. His incredible talents and successes in the boxing ring, combined with his unprecedented personality and showmanship, made him the most well-known athlete in the world during his heyday. Ali won 56 of his 61 career fights, and became the heavyweight champion of the world three separate times. Ali’s prominence also made him an integral figure in the Civil Rights movement of the 1960’s as well.

1. Michael Jordan – Talking about Michael Jeffrey Jordan is like talking about a folk hero or even a superhero. He is, without question, the greatest player in NBA history, and the man to whom every player — past, present, and future — will be compared. In the 1990’s, Jordan won six NBA championships, and likely would’ve won a couple more if he didn’t take the two-year sabbatical from the NBA. Under Jordan, 1995-1996 Chicago Bulls are considered to the greatest NBA team of all time. We use a tone of voice when describing his feats and accomplishments like they’re legends that us regular mortals cannot aspire to duplicate. He inspires equal parts admiration, awe, and fear from his teammates, contemporaries, and fans. In addition, he certainly equaled — if not surpassed — Muhammad Ali as the biggest sports icon in the world.

Honorable Mentions – It just wouldn’t be fair to end this article without mentioning Babe Ruth, Magic Johnson, Kareem Abdul-Jabbar, Martina Navratilova and Gordie Howe. Did we miss anyone?

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