Babe Ruth signed a contract for just $600 during his first year of baseball in 1914. More than a century later in 2020, another Yankee named Gerrit Cole signed a contract that will pay him an average of $36 million a year for a total of $324 million over nine years. Rich is a subjective term, but the country’s highest-paid athletes have always had a pretty sweet deal. Since it’s not always possible to quantify who, exactly, had the most money in any given decade, this article will introduce you to some of the richest and best-paid athletes.
Last updated: Oct. 29, 2020
Pictured: Just a few days after sweeping the Pittsburgh Pirates in the World Series, New York Yankees stars Babe Ruth, left, and Lou Gehrig pose at an exhibition game during a postseason barnstorming tour in October 1927.
The 1920s are often called the Golden Age of Sports. That decade saw a post-war economic boom, a social revolution, the emergence of the United States as a global superpower and the rise of true international movie stars and celebrity athletes. The biggest athletes of the decade broke the mold of owners truly owning players and rose to fame and fortune on the backs of unimaginably rich salaries, the likes of which wouldn’t be seen again for some time to come.
Tyrus Raymond “Ty” Cobb is one of the greatest hitters in history as well as one of the most controversial personalities. He earned $2,500 during his first year in Detroit in 1907. By the 1920s, he was a wealthy superstar. He earned a massive $85,000 in 1927, more than Babe Ruth made three years later, and by the time he died in 1961, he had a fortune of $12.1 million.
From early on, Cobb displayed investing acumen that nearly matched his performance on the field. He used his already hefty salary to amass huge financial holdings, including tens of thousands of shares of Coca-Cola and General Motors, mineral holdings, blue-chip stocks, bonds and dividend-paying securities, according to the Los Angles Times.
Each Golden Age sport had its golden boy, and in boxing, it was certainly Jack Dempsey. Heavyweight champion from 1919-1926, Dempsey and his promotor broke all the attendance records of the time, according to USA Today. He fought in the boxing world’s first $1 million gate as well as its first $2 million gate and earned $717,000 in a single fight in 1926. Compared to Ruth’s $80,000 a year, Dempsey put the Bambino — and all other athletes of his day — to shame.
Harold “Red” Grange was the first true NFL star. Iconic Chicago Bears owner George Halas — Halas spearheaded the creation of the NFL — signed Grange in 1925. The complex and lucrative deal was unlike any in sports. According to Forbes, it included a share of the gate, endorsements and even a movie deal. In the end, it netted Grange a payout that was unimaginable to football players of his era — $200,000.
At the height of his career, George Herman “Babe” Ruth was probably the most famous celebrity in the world and remains one of the best-known baseball players of all time. He was paid $600 for his inaugural year in Baltimore in 1914, according to the Baseball Almanac.
By 1919, the Red Sox were paying him $10,000, but that year — in what has since been known as the “Curse of the Bambino”— the Sox traded Ruth to the Yankees. In 1920, his salary doubled to $20,000 in New York, then to $30,000 the next year, then to $52,000 the year after that. Up and up it went all the way to a then-astronomical $80,000 a year at his peak in 1930 and 1931.
As late as 1931, the biggest Golden Age stars were still enjoying enormous salaries. That, however, all changed as the Great Depression flattened wages from top to bottom. Babe Ruth, for example, earned $80,000 in both 1930 and 1931, but by ’32, the highest-paid player earned $75,000. The next year that dropped to $52,000, then to $35,000 the year after that, according to the Society for American Baseball Research (SABR). The top salary in the league would remain in the $30,000s through 1940. In terms of dollars and cents, at least, the Golden Age was over.
According to Time, the Detroit Tigers paid Connie Mack of the Philadelphia Athletics $100,000 in 1934 to acquire Mickey Cochrane, the greatest catcher of his day and one of the greatest of all time. The Hall of Famer’s presence was immediately felt. The Tigers roared to two back-to-back AL pennants and their first world championship. Cochrane played the unique role of catcher-manager, and although SABR reports his salary at $36,000 for 1936-37 — the highest-paid player in the league both years — Time speculated in 1938 that his manager salary could have been as high as $45,000. In 1937, Cochrane was nearly killed when a pitched ball cracked his skull and ended his playing career. He was relegated to the role of manager and fired the very next year.
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In 1936, Joe DiMaggio was a post-Ruth rookie phenom and his teammate, Lou Gehrig, was a seasoned veteran from the Golden Age. In 1935, Gehrig earned only $31,000 but was the highest-paid player in the league, according to SABR. Perhaps trying to reclaim some of the Golden Age glory, Gehrig asked for $50,000 for the next season but was offered the same salary of $31,000 — DiMaggio was offered only $15,000. According to Bleacher Report, powerful owners across the league were playing hardball with stars who they believed had been wildly overpaid in the past — they were not nostalgic for the ’20s. Both DiMaggio and Gehrig held out but eventually, both men folded for little more than what they were originally offered.
The first half of the 1940s was dominated by World War II, which saw entire sports leagues suspended and postponed across the country as even famous and celebrated men of fighting age went off to war. This led to new opportunities for women both in the factory and on the field with the emergence of women-based franchises like the kind made famous in “A League of Their Own.” When the war ended, sports came roaring back — but the world it came roaring back to had changed. Jackie Robinson broke the color barrier that decade and Hank Greenberg defied anti-Semitism.
In the offseason before his legendary 1941 season — a hit in 56 straight games, a world championship and an MVP Award — legendary Yankee Joe DiMaggio shocked the sports world when he asked for $40,000, according to USA Today. It was nothing close to Golden Age wages of yesteryear, but certainly high for the Depression-era that was now passing. The average annual income for Americans in 1940 was $1,368. DiMaggio wound up getting $37,500, but he would go on to become an early six-figure ballplayer and the top-earning player in baseball for several years during the 1940s.
One of the greatest Detroit Tigers sluggers of all time, “Hammerin’” Hank Greenberg finished a 13-year career with a .313 batting average and 331 home runs despite losing four years of his prime to World War II. With 58 homers in 1938, he came close to toppling Babe Ruth’s record. He was the highest-paid player for four years of his career, according to SABR, all but one of which was in the 1940s. He became the first player ever to earn $100,000 a year, according to the Los Angeles Times, not to mention the first Jewish member of the Baseball Hall of Fame.
One of the most significant African-American athletes in history, boxer Joe Louis won the heavyweight crown in 1937 when he knocked out James Braddock. During the next 12 years, virtually all of the ’40s, Louis successfully defended his belt 24 times, earning roughly $4 million in prize money along the way, according to the Atlantic. Enormously generous and patriotic, Louis gave massive sums of money to family, friends and causes — many of them military in nature — and volunteered to enlist during World War II. He failed to keep up, however, with rapidly changing tax laws that increasingly targeted wealthy Americans. The late years of his life were consumed by relentless IRS pressure and he ultimately died broke and in debt.
The 1950s were a time of enormous change as athletes like Jim Brown, Hank Aaron, Mickey Mantle and Willie Mays swept in to replace the old guard of their sports. A boxer named Rocky dominated the decade, leagues were integrated and hockey began to gain national prominence. Perhaps most importantly, however, the ’50s launched the era of televised sports.
Yogi Berra was one of the greatest — not to mention most marketable — Yankees of all time, but he was also one of the richest athletes of the 1950s mostly because he changed the nature of the business of baseball.
Yogi Berra was the first player ever to have an agent negotiate endorsement deals on his behalf, according to CNN, most notably for his service as the spokesman for Yoo-hoo chocolate drink. Soon, all the big players started realizing that their fame could earn them more in endorsement deals than their talent earned them on the field.
Legendary Cleveland Browns quarterback Otto Graham joined the NFL in 1950 after dominating in the All-America Football Conference during that league’s four seasons after World War II. He led the Browns to the title game six seasons in a row and won three championships. When he considered retiring after the 1954 season, the Browns offered Graham a $25,000 contract to stay — it was the highest salary in the entire league back then, according to The New York Times.
In 1947, Rocky Marciano knocked out Lee Epperson in the third round of a highly anticipated fight. It was the beginning of what boxing historians refer to as “The Streak.” Eight years later in 1955, Marciano hung up the gloves with a record of 49-0. During the course of his astonishing career, the original Rocky earned a combined $1.7 million, according to ESPN, making him one of the richest athletes of the decade.
A Boston Red Sox legend and one of the greatest hitters of all time, Ted Williams remains the last Major League Baseball player to finish a season with a .400 batting average — .406, to be exact. In 1949, both he and Yankees rival Joe DiMaggio got raises that brought their salaries to $100,000, according to the St. Louis Post-Dispatch. A decade later in 1959, Williams earned $125,000 in what was the last year in his 10-year run as the highest-earning player in baseball.
The 1960s were among the most dynamic decades in sports. It began with Roger Maris dethroning Babe Ruth as the single-season home run king and ended with Joe Namath guaranteeing an upset Super Bowl victory — and delivering. A Celtics dynasty ruled still-emerging professional basketball, Muhammad Ali was at the center of one of the greatest eras in boxing history and NASCAR began attracting legions of race fans from small towns and rural America.
On Aug. 25, 1965, Celtics great Bill Russell signed a contract that made him the NBA’s highest-paid player with a salary of $100,001 — exactly $1 more than the salary of his arch-rival Wilt Chamberlain. The most dominant player of his era and perhaps of all time, Chamberlain is still the only player ever to have scored 100 points in a single game, which he did in 1962 — it remains the greatest record in basketball.
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Only three baseball players in history have earned the highest salary in the league for 10 years or more, according to SABR. Babe Ruth was the top dog 14 times, Alex Rodriguez claimed the title of the MLB’s highest-paid player 12 times and Willie Mays did it 11 times. In 1959, Mays was at the top of the league with a $75,000 salary. His last year at the top was 1970 when he earned $135,000. He had the highest salary every year between those two years except for one — Sandy Koufax had the top salary in ’66.
Arnold Palmer is one of the greatest and most accomplished golfers of all time, and he rose to prominence in the 1950s as his legendary charisma translated well through the new medium of television. By the 1960s, he was the sport’s biggest star and was partly responsible for extending golf’s appeal beyond the country club class to regular working Americans. He was also a hugely successful businessman and endorsement spokesman both during and after his career, according to Forbes. He earned only $3.6 million in prize money during his 52 years on the PGA and Champions tours, but he died with a nearly $1 billion fortune. He still earned more than $40 million the year after he died.
About 60 million people watched on Jan. 12, 1969, as “Broadway Joe” Namath made good on his public promise to lead his New York Jets to an upset over the heavily favored Baltimore Colts in Super Bowl III. The Colts were led by Hall of Fame quarterback Johnny Unitas. The NFL didn’t make payroll figures public then, according to U.S. News & World Report, but the average player was believed to have made about $25,000. At least half the league made at least $20,000 — not bad money at a time when the average U.S. salary was $5,900. Unitas, however, was believed to have earned more than $100,000 annually.
The most significant event in sports in the 1970s was the murder of Israeli athletes by Palestinian terrorists at the 1972 Munich Olympics. There were plenty of high points, too, however, in a decade that saw Sugar Ray Leonard win his first world boxing title, Pele play his last game and Reggie Jackson start a new era in Yankees history.
On April 8, 1974, Hank Aaron hit career home run No. 715, toppling Babe Ruth’s lifetime tally once and for all. Two years earlier in 1972, Aaron became the highest-paid player in baseball, according to the St. Louis Post-Dispatch, when he signed a three-year, $200,000 a year contract. By that point, he already had 639 home runs. The slugger earned less than $35,000 when he was named league MVP in 1957.
The goggles. The skyhook. The records. Aside from being the all-time leading scorer in NBA history, Laker great Kareem Abdul-Jabbar was named NBA MVP six times. When the Bucks traded Abdul-Jabbar to the Lakers in 1975 after drafting him six years earlier, The New York Times estimated the big man was earning $500,000 a year.
Muhammad Ali’s most thrilling and famous fights took place in the ’70s. The Rumble in the Jungle with George Foreman and the Thrilla in Manila versus Joe Frazier are considered two of the greatest sporting events in the 20th century. Ali, who was guaranteed $4.5 million for the Thrilla in Manila fight alone, died with an estimated fortune of $80 million, according to Forbes.
Jack Nicklaus was one of golf’s biggest stars in the 1960s and ’70s and was widely influential in expanding the game from a niche for the rich to the mainstream status it enjoys today. He spent the decade tallying PGA Tour tournaments too numerous to list, winning majors and earning the top nod as PGA Player of the Year. Today the 80-year-old Nicklaus is worth $320 million, according to Celebrity Net Worth, although the vast majority of that has come from his business dealings, endorsement contracts and, most notably, his vast golf course design empire.
Quarterback and Vietnam veteran Roger Staubach was a 27-year-old rookie who worked a real estate job on the side when he signed a $25,000 contract with the Dallas Cowboys in 1969, according to Sports Illustrated. By the time he retired in 1979, the team’s general manager offered the future Hall of Famer $750,000 a year for two years to stay on for a couple more seasons. Staubach refused — he wanted to make real money. Staubach fell back on his day job and became one of the biggest and most successful real estate developers in America. He has a net worth of $600 million, according to Celebrity Net Worth, and remains a perennial contender for the title of highest-earning former NFL star.
For sports fans, few decades were more dramatic and exciting than the 1980s, which witnessed an overlapping of perhaps the greatest dynasties ever assembled in hockey (Gretzky’s Oilers), football (Montana’s 49ers) and basketball (Jordan’s Bulls). Financially, it was the first time in history that the words “athlete” and “millionaire” became synonymous.
When Wayne Gretzky retired, he owned or shared 61 NHL records, including most goals, most goals in one season, most assists and most assists in one season. The greatest hockey player of all time, the legendary Canadian led the Edmonton Oilers to an astonishing four Stanley Cup victories: 1983-84, ’84-’85, ’86-’87, and ’87-’88. When he shocked Canada and the world in leaving Edmonton for an NHL outpost in Los Angeles to join the Kings in 1990, the Los Angeles Times reported his contract to be worth $22.3 million over 16 years.
Earvin “Magic” Johnson has a fortune of $600 million, according to Celebrity Net Worth, thanks to not just a lucrative career as one of the greatest basketball players, but also as a highly successful post-career businessman. In 1981, the Laker great signed the longest, richest and most unusual contract in sports at that time. That year, Los Angeles signed Johnson to a 25-year, $25 million contract that extended through 2009 and guaranteed him a management role with the team after he retired.
Sugar Ray Leonard
Sugar Ray Leonard ranks among the greatest and most marketable boxers in history, and his career spanned the 1970s through the ’90s, but the ’80s was his heydey. He — along with Roberto Duran, Marvin Hagler and Tommy Hearns — was part of the famous “Fabulous Four” rivalry that captivated boxing fans of the era. In 1989, the Los Angeles Times reported that Leonard’s earnings had reached $83.5 million and topped nine digits when factoring in endorsement deals.
Until the arrival of Tom Brady, there was essentially no argument that Joe Montana was the greatest quarterback of all time. He led the San Francisco 49ers to four Super Bowl championships and won three Super Bowl MVP titles through a series of dazzling and dramatic victories that were characterized by thrilling comebacks, often in conjunction with his right-hand man, wide receiver Jerry Rice. He earned nearly $25.56 million between 1979-1994.
Every baseball fan in Philadelphia knows the name Mike Schmidt, a two-time National League Most Valuable Player and six-time National League home-run leader. He was paid handsomely for his efforts. Schmidt was the highest-paid player in baseball for six seasons between 1977 and 1985, according to SABR, and was earning about $2 million a year by 1984.
In 1992, the U.S. Olympic basketball Dream Team became the most dominant team ever assembled in any sport. Also in the decade, women put the United States on the global stage of soccer by winning the World Cup twice, and crossover athletes like Bo Jackson and Deion Sanders changed the game in terms of sports marketing.
For the New York Mets faithful, July 1 is Bobby Bonilla Day. On the first day of the seventh month of every year between 2011-2035, that other New York baseball team is contracted to pay the famous switch-hitter nearly $1.2 million. In 2000, the Mets cut Bonilla and bought out the $5.9 million remaining on his contract, according to ESPN. They chose, however, to finance it over 25 years at a rate of 8% interest. In the early ’90s, Bonilla was the highest-paid player in baseball for three years straight, according to SABR.
Nick Faldo was one of the greatest golfers of his generation, racking up 34 non-Tour victories, 33 international victories and nine PGA Tour wins, including the Masters in 1989, ’90 and ’96. He earned more than $6 million on the course alone, not counting endorsements.
Arguably the greatest basketball player in history and one of the most recognizable celebrities for more than three decades, Michael Jordan led the Chicago Bulls to six titles. He earned about $90 million on the court, according to Forbes, but his real money came from his sponsorships. Jordan changed the nature of celebrity endorsement deals forever through enormous contracts with Nike, Gatorade, Hanes and many more. Three out of four NBA players take the court in Jordan brand sneakers. He bought a majority stake in the Charlotte Hornets in 2010 and is now worth $2.1 billion, according to Forbes.
Mike Tyson’s career represents one of the fastest rises in sports history. Once the youngest heavyweight champion in history and the most feared fighter, his downfall was equally fast and furious. Tyson earned $400 million during the course of his career, according to Forbes, but by 2003, he’d declared bankruptcy after a long and highly public string of struggles that had culminated in a long prison sentence.
Steve Young was tasked with filling the enormous shoes of Joe Montana, and fill them he did. With three Super Bowl victories, seven trips to the Pro Bowl and three All-Pro selections, Young extended the 49ers’ amazing record of winning through the 1990s. Between 1985-1999, Steve Young earned nearly $50 million on the field alone.
Icons rose and fell in the first decade of the 21st century as the world met LeBron James and learned to place asterisks next to records set by steroid-enhanced baseball heroes. There was also an NBA referee betting scandal, an NHL lockout and the rise of the NFL over baseball as America’s favorite pastime.
Green Bay Packer Brett Favre was one of the winningest and most beloved quarterbacks of his era. In 1997, the Packers signed Favre to a seven-year, $47.25 million contract that included a $12 million signing bonus. At the time, it was the richest contract in football history. Favre’s Hall of Fame career spanned through the 1990s and 2000s and included 11 trips to the Pro Bowl, three MVP titles and a Super Bowl victory.
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According to Forbes, Roger Federer is “the greatest men’s tennis player of all time.” He’s earned at least $124 million on the court, but even that hefty sum pales in comparison to what he has been paid from appearance and endorsement deals. He has a fortune of $450 million, according to Celebrity Net Worth, and in 2018, he struck a 10-year, $300 million deal with the Japanese brand Uniqlo, as reported by Forbes.
Kevin Garnett stormed into the NBA in the late 1990s and played all the way through the mid-2010s. A 15-time All-Star and nine-time All-NBA electee, Garnett will be remembered as one of the greatest and most dynamic power forwards in basketball history. He pulled in massive, eight-figure salaries for 16 seasons in a row. Overall, he earned more than $334 million on the court alone.
Alex Rodriquez was already in the middle of a record-breaking $252 million deal with the Texas Rangers when he smashed all salary records yet again by signing a 10-year, $275 million contract with the New York Yankees in 2007. The sheer size of the deal changed the game for athlete salaries across all major sports. The Rangers will continue to pay him through 2025, according to Sports Illustrated. During the course of his career, Alex Rodriguez earned more than $450 million.
Despite the greats who came before, the arrival of Tiger Woods changed golf forever. A man of color in a historically white sport, Tiger Woods remains the winningest golfer in history with a record-setting 82 PGA Tour wins. The 2000s was the decade of Tiger. He started the century with nine wins in 2000 alone, including the PGA Championship, the Open Championship and the U.S. Open. One of the most marketable athletes across all sports, he has a net worth of $800 million, according to Celebrity Net Worth, and earned more than $1.4 billion in sponsorship deals over the course of his career, according to Forbes.
In the 2010s, once-ubiquitous yellow Livestrong bracelets were falling out of favor as Lance Armstrong’s world came crumbling down in a doping scandal, the football world learned the word “Deflategate” and the Astros found themselves at the center of a sign-stealing scandal. As athletes became social media influencers, Tom Brady cemented his status as the greatest quarterback of all time in the 2010s, and the world mourned the loss of Muhammad Ali, Kobe Bryant and George Steinbrenner. Also, fans and athletes alike woke up to the dangers of concussions.
Serbian tennis great Novak Djokovic pulled in $50.6 million in 2019. His 15 titles put him behind only Federer and Raphael Nadal in terms of Grand Slam wins. He boasts an eight-figure yearly endorsement portfolio and his $132 million in cumulative prize money is the highest on-court haul of all time.
Michael Jordan was almost universally considered to be the greatest basketball in history until LeBron James came along — now, many credible people think King James is truly the king. It’s hard to overstate James’ dominance both on the court and in the world of celebrity contracts — he boasts the NBA’s top endorsement portfolio by far, according to Forbes. In 2018, he joined the Lakers as part of a four-year, $153 million deal. He has a net worth of $480 million, according to Celebrity Net Worth.
Part of a royal football dynasty that includes his brother, Peyton, and his father, Archie, Eli Manning is one of the greatest quarterbacks in Giants history. He went to the Pro Bowl four times and led New York to two Super Bowl championships. Over the course of his career, he earned more than $252 million across 16 seasons.
No celebrity in the 2010s can compare their earnings to those of Floyd Mayweather, who pulled in an astonishing $915 million during the past decade alone. He did it all on his own — no team, no sponsorship deals, no promoter. Nicknamed “Money” and widely considered to be the best pound-for-pound boxer in history, he retired unbeaten with a record of 50-0.
Albert Pujols was Rookie of the Year, a three-time MVP, won two Gold Gloves, a batting title and two World Series. He has earned nearly $300 million over the course of his career with the Cardinals and the Angels, pulling in eight-figure salaries every single year since 2005.
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