25 Biggest and Most Expensive Sports Contracts Ever Signed

Sports contracts over the years have gotten so extreme that they make even wealthy people envious. It wasn’t always like this, this era of contracts started in the late 80’s with Kirby Puckett being the first player to receive a $3 million dollar contract in 1989 according to the Sporting News. That might not seem like a lot, but for MLB, it was a great deal at that time. And it did not stop there. That was just what opened the flood gates.

Here’s a detailed breakdown of the 25 biggest and most expensive sports contracts ever signed (in descending order).

1 – Jason Giambi – New York Yankees – Baseball – $120,000,000

These days, Jason Giambi seems more of a DH than a power hitting first baseman. That said, he was once the power hitting first baseman for the Oakland Athletics, but when Mark McQuire was traded in 1997, Jason became the first baseman.

In 2003, Giambi was named in the Balco investigation, blemishing his otherwise promising career. Since then, he apologized to the organization as well as the fans and promised to return to his previous form.





2 – Shaquille O’Neal – Los Angeles Lakers – Basketball – $120,000,000

Shaquille O’Neal originally played college basketball for the LSU tigers. He is probably one of the biggest players in the NBA to come along since Kareem Abdul-Jabbar or Wilt Chamberlain, and we’re not referring to his stature. The contract in question was signed in 1996 and ran through the 2003 season and made NBA history.

Shaq, as he is endearingly called, spent the first 4 years of his career with the Orlando Magic where he helped them win 20 more games than in the previous year, and made his first NBA All-Star game in1993. Shaq is also one of the few players that has a better average shooting field goals (.581 lifetime) than he does with free throws (.524 lifetime).




3 – Mike Hampton – Colorado Rockies – Baseball – $121,000,000

Mike Hampton signed an 8 year deal with the Colorado Rockies worth $121,000,000 in 2001. What’s interesting about this deal is that Hampton hasn’t even pitched extensively since August 19, 2005. He faced several injuries in 2005, and underwent Tommy Johns surgery to repair his throwing arm.

In 2002, a year after the contract was signed, the Rockies traded him to the Florida Marlins, who then proceeded to trade him to the Atlanta Braves. Once in Atlanta, Mike was able to work with then pitching coach Leo Mazzone who helped him get out of the funk he had gotten himself into while in Colorado.


4 – Tim Duncan – San Antonio Spurs – Basketball – $122,007,704

Tim Duncan’s contract runs through the 2010 season with the San Antonio Spurs. Tim was born on the US Virgin Island of Saint Croix, and is still featured prominently on billboards all over St. Croix. Duncan was originally picked in the 1997 draft by the Spurs after a stellar college career for the Wake Forest Demon Decons.

Tim Duncan’s entire professional career has been with this one team, which in today’s sports, is remarkable in itself. Tim holds many awards, including the 1998 NBA Rookie of the year, 2002 and 2003 NBA MVP, 1999, 2003, and 2005 NBA Finals MVP, and a 4 time NBA Champion. He was on the winning team in 1999, 2003, 2005, and 2007.





5 – Chris Webber – Sacramento Kings – Basketball – $122,718,750

Chris Webber might be best known as a member of the famed Fab Five for the Michigan Wolverines. This group of five outstanding players all entered into college in 1991 and took their team to the finals twice, but did not win. In the 1993 draft, he was selected by the Orlando Magic who then proceeded to trade him to the Golden State Warriors. Chris played there through 1994 when he was traded to the Washington Bullets where he played until 1998. In May of that year, Chris was traded again; this time he was going to the Sacramento Kings. In 2001, the Kings locked him into a 7 year deal, but traded him once again in 2005, this time to Philidephia. Chris is still playing today as he has come full circle, playing in 2008 for the Golden State Warriors.





6 – Alexander Ovechkin – Washington Capitals – Ice hockey – $124,000,000

This is by far the longest contract that made this list. In 2008 the Washington Capitals of the National Hockey League signed Alexander Ovechkin to the biggest contract of the league. He was originally drafted by the Capitals in the 2004 NHL Entry Draft first overall. Due to the 2004-05 NHL lockout, Ovechkin did not start playing in the NHL until the 2005 season, but when he did start playing, he became the first rookie that was named to the NHL First All-Star Team in 15 years.

Overchkin’s performance, and therefore his value continued to rise the more he played and continued to set records and collect rewards. On January 13, 2008, ESPN reported that Ovechkin and Washington Capital had come to terms on this 13 year contract for $124 million.




7 – Michael Schumacher – Ferrari – Auto racing – $124,000,000

In 1996, Michael Schumacher and Ferrari came to an agreement on a 4 year contract. One of the most amazing things was that out of the 7 championships that Schumacher won, none of them was during this span. His first two championships were 1994 and 1995 and his last 5 were 2000 – 2004. The first titles he was racing for the Benetton-Ford team.

Schumacher made his debut Formula One race at the 1991 Belgian Grand Prix for the Jordan-Ford team, wining his last five titles. Schumacher decided to retire in 2006 from Formula One racing and later came back as an advisor to Ferrari and Jean Todt’s super assistant in 2007.



8 – Rashard Lewis – Orlando Magic – Basketball – $126,000,000

In July of 2007, the Orlando Magic and Rashard Lewis came to an agreement in a contract that would lock him in for 6 years and pay him $118 million dollars over those 6 years. After spending the first 9 years of his career with the Seattle SuperSonics, he opted out of his final 2 years on May 25, 2007.

Rashard has averaged 16.8 points a game over his 10 year career. Rashard never played college ball as he opted out and went into the 1998 NBA draft. He was selected by the SuperSonics in the third pick of the second round that year, making him the 32nd pick overall. Lewis has been to the playoffs a total of 4 times, three times with Seattle and the last time (07-08 season) with Orlando. He holds an average of 17.1 points during the playoffs


9 – Vernon Wells – Toronto Blue Jays – Baseball – $126,000,000

December 15, 2006 saw Vernon Wells locked in with the Toronto Blue Jays on a seven year contract that would pay him $126 million dollars over that time. This contract will take him through the 2014 season and includes a “no trade” clause in it as well to protect the interest of Wells.

Vernon broke into pro baseball when he entered the amateur draft in 1997 and was selected by Toronto in the first round as the fifth overall pick. He bounced through the organization until he got his shot in 2002 with the Major League club. He belongs to the Top 500 home run hitters of all time list.


10 – Barry Zito – San Francisco Giants – Baseball – $126,000,000

Barry Zito locked into a 7 year deal with the San Francisco Giants worth $126 million dollars. Barry has become one of the dominant left-handed pitchers of the decade. He was originally drafted in 1996 by the Seattle Mariners and again in 1998 by the Texas Rangers, but did not sign with either of these teams.

Instead, he finished his college days at USC after transferring from Los Angeles Pierce College (and UC Santa Barbara before that). Barry was drafted again by the Oakland Athletics in 1999 and made major league debut against the Anaheim Angels on July 22, 2000. He pitched for the Athletics from 2000 to 2006.


11 – Kevin Garnett – Minnesota Timberwolves – Basketball – $126,000,000

Kevin Garnett is currently playing for the NBA’s Boston Celtics. When he was with the Minnesota Timberwolves, he had signed a seven year deal with the Timberwolves that would pay him $126 million dollars. Garnett was originally drafted in the 1995 NBA draft and was the first player since Moses Malone to be drafted right out of high school since 1974.

Minnesota decided that this would be their Franchise Player but they became increasingly frustrated with him starting in 2004 and through 2007 due to issues with the team and their inability to win. On July 31st of 2007, all of that was remedied as Kevin was traded to the Boston Celtics. Ironically enough, he would go on to win a NBA Championship with the Boston Celtics in 2008.


12 – Jermaine O’Neal – Indiana Pacers – Basketball – $126,558,000

Jermaine O’Neal is another player that never graced the floor of a college basketball team. A 6′ 11″, he declared his NBA eligibility in the 1996 draft. He was taken 17th overall by the Portland Trail Blazers that year. From the day O’Neal entered the league, till the time he was traded to the Indiana Pacer, O’Neal believed that he was treated unfairly.

O’Neal spent most of his time in Portland on their bench and was eventually traded to the Pacers where he debuted as a starter in the 2001 season. The Pacers were so impressed with O’Neal that on Jul 16, 2003, they decided to give Jermaine a six year deal that held a value of $126,558,000.


13 – Peyton Manning – Indianapolis Colts – Football – $132,500,000

Peyton Manning got his long term contract in 2005 when he signed on with the Indianapolis Colts. Peyton had already spent 7 years in Indianapolis as the Colts quarterback, and in 2004 he would have a record setting season (which was one of the main reasons the Colts wanted to desperately lock him in for the remainder of his career).

While still in college, Manning had amassed 11,201 yards and 89 touchdowns, winning 39 of 45 games as a starter, and becoming the Volunteer’s all-time leading passer. His highlights, records, and awards would not stop there though. In 2006, the Colts had their best season yet as Peyton led them to a Superbowl Championship against the Chicago Bears in Super Bowl XLI.


14 – Alfonso Soriano – Chicago Cubs – Baseball – $136,000,000

Alfonso Soriano has made a name for himself during the New York Yankee years as their lead off hitter. He has made the 30-30 club, the 40-40 club, and is part of the Top 500 home run hitters of all time just to name a few of his achievements so far. 2001 was Soriano’s rookie year and he finished third in the Rookie of the Year award.

In 2004, Alfonso was traded to the Texas Rangers along with a minor leaguer for Alex Rodriguez and a cash compensation of $67 million. Soriano played in Texas through the 2005 season when in December, he was traded again. The Chicago Cubs also offered him an eight-year contract worth nearly $136 million dollars which he accepted.


15 – Kobe Bryant – Los Angeles Lakers – Basketball – $136,400,000

Kobe Bryant’s 7-year contract with the Los Angeles Lakers gives him the title of the most expensive Basketball contract of all time. Kobe has been instrumental in leading the Lakers to 3 consecutive NBA Championships between 2000 and 2002. He made history when he became the first guard to ever be drafted out of high school in 1996, giving him instant notoriety.

Kobe’s contract came around the same time that the Lakers decided it was time to part ways with Shaquille O’Neal in favor of building their team around Kobe. Unfortunately, the Lakers have not won another NBA Championship since then (even as Kobe has ammassed numerous awards and achievements).


16 – Johan Santana – New York Mets – Baseball – $137,500,000

Johan Santana had one of the biggest and most talked about trade potentials in baseball’s off season. The New York Mets signed him to a 6-year, $137 million dollar contract that would make him the highest paid pitcher in the Major Leagues. And well-deserved when you look at what he can do to an offense. Santana debuted with the Minnesota Twins on April 3, 2000 and came out of the bullpen against the Tampa Bay Devil Rays, as they were known then. He got his first major league start against the Kansas City Royals on August 7, 2000.

Santana holds a 3.29 career ERA that teams lovem and opponents are batting just .219 lifetime against him. With masterful control, he might be one of the greatest left handed pitchers to grace the mound in some time.



17 – Todd Helton – Colorado Rockies – Baseball – $151,500,000

Todd Helton, born in Knoxville, Tennessee, holds the second longest contract of this list at 11 years. He originally signed this long term deal in 2001, which was stated as a 9 year extension to his current contract. He also has an option for the 2012 season. Todd has accomplished a number of notable achievements over the years, including 5 time All-Star and a 3 time Gold Glove winner.

Todd was drafted in his junior year in the first round, eighth overall, in the 1995 Major League Baseball Draft by the Colorado Rockies. He was signed in July of the same year. Todd has spent his entire career with the Colorado Rockies and only recently have talks started about trading him away.


18 – Miguel Cabrera – Detroit Tigers – Baseball – $152,300,000

Miguel Cabrera busted on the scene in 2003 in style with the Florida Marlins by hitting a walk off home run in his first major league game on June 20, 2003. He was just 20 years old. His bat was so good that he was very instrumental in the playoffs for the Florida Marlins and was a huge part of them beating the Yankees that year. Miguel would end up on the cover of the ESPN magazine during the off season due to his exceptional statistics which showed no signs of tapering off. In December of 2007, the Marlins agreed on a deal that would send Cabrera and team mate Dontrelle Willis to the Tigers for 6 players. In March of 2008, Miguel Cabrera and the Detroit Tigers came to an agreement on his most impressive contract of his still young career. It is an 8 year deal that will take him through the 2015 season.




19 – Kimi Räikkönen – Ferrari – Auto Racing – $153,000,000


2007 saw Ferrari snap up one of the best drivers in Formula One Racing and giving him the second largest contract in racing history. Kimi Räikkönen busted on the scene in 2001 with the Sauber Formula One team and soon enough, he left them for McLaren where he would stay until 2006. During that span he was only able to muster a second place finish twice. The other 3 years saw a 6th place finish in 2002, a 7th place finish in 2004, and a 5th place finish in 2006. Kimi did not see success until 2007 when he moved to Ferrari. He was able to capture a 1st place finish in 2007 and currently is 2nd in 2008. His career was plagued with technical problems which caused 38% of his races to end in retirement.





20 – Fernando Alonso – McLaren – Auto Racing – $160,000,000

Even though McLaren™ decided to make Fernando the highest paid driver on the Formula One circuit in 2007, Alonso didn’t stick around for the 4 years of the contract due to an “on again, off again” relationship over the next two years. Alonzo started his F1 career with Minardi in 2001, as the third youngest driver ever to start a Formula One race when he debuted at the 2001 Australian Grand Prix. On August 24, 2003, Alonso would be the youngest driver ever to win a Formula One race when he took the checkered flag at the 2003 Hungarian Grand Prix. On December 19, 2005, Alonso announced that he would be moving to McLaren in 2007 after his contract expired with Renault. In 2008, Alonso would be back in a Renault owned car.


21 – Manny Ramirez – Boston Redsox – Baseball – $160,000,000

When Manny Ramirez signed this contract, it made him the highest paid Red Sox player of all time.

His strong bat has led him to be one of the most feared power hitters and placing him in the group of 24 sluggers that have hit 500 or more home runs.







22 – Michael Vick – Atlanta Falcons – Football – $167,000,000

Michael Vick had a celebrated career at Virginia Tech prior to be drafted by the Falcons in 2001. He joined Tommy Nobis, Steve Bartkowski, and Aundray Bruce as the Falcons only #1 overall picks in all of club history. Michael’s contract was short lived as he is currently serving a sentence for issues relating to his property in Virginia. His contract was signed in 2005 and extended to 2014. It remains to be seen if he can come back to the Falcons and even if he can, will he still have the effect that he once had.




23 – Derek Jeter – New York Yankees – Baseball – $189,000,000

One of only 2 baseball players with a 10-year contract, Derek Jeter started his career as a Yankee in 1992 as he was drafted 6th overall and has always worn the pinstripes. He has earned himself the name of Mr. Yankee, and is currently listed as the Yankees’ captain. He has also played in 9 All-Star games representing the New York Yankees and ranks in the top ten in the production catergories of hits (second), runs (fourth), and batting average (seventh). Derek signed his new 10-year contract in 2001. It currently runs through 2011.


24 – Alex Rodriguez – Texas Rangers – Baseball – $252,000,000

Alex received his first major contract in Texas when he became a free agent after the 2000 season was over. The Texas Rangers needed someone to build their team around after hitting rock bottom, and Alex seemed like the perfect player for the job. Unfortunately, however, A-Rod did not seem to be working for Texas as in 2001 and 2002 they still finished in the cellar of their division. It was time to let Alex go, and Texas did exactly that, right before the start of the 2004 season.




25 – Alex Rodriguez – New York Yankees – Baseball – $275,000,000

One of only 2 baseball players with a 10 year contract, Alex was originally traded to the Yankees on February 15, 2004 to replace a void created when then third baseman Aaron Boone injured his knee in a pick-up game of basketball. This injury put him out for the entire year. Furthermore, Texas had already been looking for a place to dump Alex and his enormous salary and this was just the opening that they had wanted. The re-signing of Rodriquez was strange to say the least as he would be opting out of his $252 million dollar 10-year contract. Lucky for him, the New York Yankees picked him up soon after, and signed him to a new 10-year contract worth $275 million.

Written by Jeff Springer

Jeff Spring is the Finance & Markets Editor at BusinessPundit.com. He's currently spending his days backpacking across Europe. While he may be living outside of the United States, he stays connected to American financial markets and M&A's more than is probably healthy for any single person. His love of a good book and a Bloomberg terminal can't be understated.