The 40 Biggest Free-Agent Signings in Sports History

There are three ways you can look at what defines a "big" free-agent signing: the unprecedented or shocking monetary terms of the deal, the success that the player brought the franchise after signing the deal or the turmoil that the player caused to any number of franchises because of the deal.

In this slideshow, we'll attempt to streamline the three. Yes, there will be a few huge-money deals that won't be mentioned because that player was neither a hero nor a goat over the terms of the deal. If it was only about money, we'd really only be talking about the last decade in sports.

And yes, there will be a few positive or negative signings that won't be mentioned in this slideshow because they simply weren't very controversial or widely discussed at the time. (David Ortiz signing a one-year deal with the Red Sox in 2003 for $1.25 million was an incredible bargain, but it was hardly newsworthy at the time.)

Now show me the money.

(Note: Contract extensions won't be accepted unless in sign-and-trade situations, and we'll keep it to American sports for the sake of maintaining a more focused scope.)

40. The New York Rangers

Some teams have such a poor past with free agents that they get their own slide. We'll start with the Rangers.

All four free-agent signings failed to come anywhere close to meeting expectations. Each is widely cited when the discussion of "horrible hockey signings" is brought up.

Bobby Holik in 2002: five years, $45 million.

Chris Drury in 2007: five years, $37.5 million.

Scott Gomez in 2007: seven years, $51.5 million.

Wade Redden in 2008: six years, $39 million.

Where have you gone, Mark Messier?

39. The New York Knicks

In an era of horrific Isiah Thomas decisions as a GM, two free-agent signings stand above all others:

Jerome James in 2005: five years, $30 million.

Jared Jeffries in 2006: five years, $30 million.

If you have no idea who these players are, don't fret—they are as obscure now as they were terrible then.

Ridiculous.

38. The Washington Redskins (a.k.a. Daniel Snyder)

Daniel Snyder, you silly, silly man.

Jeff George in 1999: four years, $18 million, cut two games into his second season with the team.

Deion Sanders in 2000: seven years, $56 million, cut after one season.

Jeremiah Trotter in 2002: seven years, $35 million, cut after two seasons.

Brandon Lloyd in 2006 (he was a restricted free agent for the 49ers and cost the 'Skins a third- and fourth-round pick): $31 million deal with $10 million guaranteed; 25 catches over two years before being cut.

Adam Archuleta in 2006: seven years, $35 million, cut after one season.

37. Dana Stubblefield

One year before Snyder would buy the team, the Redskins signed defensive tackle Dana Stubblefield to a six-year, $36 million deal.

Stubblefield only played in seven games his first season and finished with seven sacks after three seasons in Washington.

And to think that we aren't even done with the Redskins yet. That's right—there's a signing so egregiously bad it simply had to be higher on this list.

36. Vlade Divac, Sacramento Kings

The Deal: Six years, $62.5 million

Why it mattered: When Divac signed with the Kings in 1999, he became a piece of the puzzle—along with Chris Webber—that began to turn the Kings from a lottery team into a championship contender.

When Mike Bibby was added via a 2001 trade, the core of the Kings was set. During Divac's time with the team, they made seven straight postseason appearances.

35. Dikembe Mutombo, Atlanta Hawks

The Deal: Five years, $50 million

Why it mattered: Denver's loss was Atlanta's gain in 1996.

Denver tried one year of run-and-gun before falling apart entirely in the hands of GM/coach Dan Issel over the next half-decade.

Mutombo missed only seven games in his four-and-a-half seasons with the Hawks, winning two Defensive Player of the Year awards and making the All-Star team four times while manning the pivot for a team that made the conference semifinals twice.

34. Curtis Martin, New York Jets

The Deal: Six years, $36 million.

Why it mattered: I'll let NFL.com do the work for me on this one.

When Bill Parcells moved on from the Patriots to the Jets, he targeted his former running back Curtis Martin as a necessary cornerstone signing for his new team. He handed the rusher such an exorbitant contract that the Patriots declined to match the offer for the restricted free agent.

In his first seven seasons with the Jets, he never rushed for fewer than 1,094 yards and had 67 total touchdowns with New York.

33. Carlos Lee, Houston Astros

The Deal: Six years, $100 million.

Why it mattered: When Lee signed this deal, he was 31 years old. In other words, the Astros were out of their caballos.

While Lee put up quality numbers from 2007-09 (averaging 28 home runs, 107 RBI and a .305 batting average), he has continued to decline with each season and is still owed $18.5 million next season.

He's putting up Mark Trumbo numbers at this point in his career but still pocketing Albert Pujols money.

32. Amar'e Stoudemire, New York Knicks

The Deal: Five years, $99.7 million

Why it mattered: It was supposed to be the first step in the super-team headed by LeBron James.

Instead, it will end up being the first step toward the super-team that will include Amar'e, Carmelo Anthony and likely Chris Paul before everything is said and done.

Either way, it was one of the premier signings in the insanity that was the 2010 NBA offseason.

31. Nnamdi Asomugha, Philadelphia Eagles

The Deal: Five years, $60 million.

Why it mattered: For one, Asomugha was the biggest free-agent name during one of the craziest free-agency periods in NFL history.

For another, he was one of a number of moves made by the Eagles this offseason, along with the signings of Jason Babin, Cullen Jenkins, Vince Young, Ronnie Brown and Steve Smith and the trading of Kevin Kolb for Dominique Rodgers-Cromartie.

If the Eagles win a Super Bowl in the next year or so, Asomugha will be a huge reason why. As it is, he will probably be a bargain at this price, as he likely could have gotten more money from either the Jets or Cowboys.

30. Alexei Yashin, New York Islanders

The Deal: After trading Bill Muckalt, defenseman Zdeno Chara and the second overall pick (used to take Jason Spezza) to Ottawa for Yashin in 2001, the Islanders then signed the restricted free agent to a 10-year, $87.5 million contract.

Why it mattered: For one, he kind of sucked considering the huge payout, averaging only 58 points over five years. The Islanders eventually had enough and decided to buy him out in 2007 for $17 million.

And they're still paying him: Even with the buyout, Yashin's contract continues to haunt the Islanders. They take an annual salary cap hit of $2.204 million—and will continue to do so through the 2014-15 season.

Yikes.

29. Julius Peppers, Chicago Bears

The Deal: Six years, $91.5 million.

Why it mattered: Peppers was the jewel of the 2010 free-agent class, landing on a Chicago defense already stacked with superstars such as Brian Urlacher and Lance Briggs.

Peppers finished the season with eight sacks, not exactly the sparkling production you would expect from such a highly-paid player. Still, Peppers is widely respected around the NFL (the players voted him the game's 10th-best player), and his contributions to the defense extend far beyond sacks.

It remains to be seen whether this contract will be a great move for the Bears or a bust. One way or another, it was a huge signing.

28. Barry Zito, San Francisco Giants

The Deal: Seven years, $126 million.

Why it mattered: The Giants' farm system has routinely churned out great starting pitchers, such as Tim Lincecum, Matt Cain, Madison Bumgarner, Jonathan Sanchez and Ryan Vogelsong.

The Giants haven't done so well securing pitching in free agency, however, as witnessed by Barry Zito.

Zito was 102-63 in seven seasons with Oakland with a 3.55 ERA, 1.25 WHIP and a Cy Young Award. In San Francisco, he is 43-61 with a 4.52 ERA, 1.40 WHIP and not so much as an All-Star game appearance.

The equivalent of dumping money into a document shredder.

(Note: Vogelsong was originally drafted by the Giants, eventually traded to the Pirates, had Tommy John surgery, recovered, went to Japan, signed with the Phillies, was released, signed with the Angels and eventually re-signed with the Giants. Whew.)

27. Rashard Lewis, Orlando Magic

The Deal: Six years, $126 million.

Why it mattered: Wait, they paid Rashard Lewis how much?

When the Magic signed Lewis in 2007, he was coming off a season in which he averaged 22.4 PPG (a career high) and 6.6 RPG. The Magic envisioned a dominant interior-perimeter combination of Dwight Howard and Lewis.

Lewis went from 18.2 PPG and 5.4 RPG during the first year of the deal to 12.2 PPG and 4.2 RPG by 2010-11, eventually being traded from Orlando to Washington for Gilbert Arenas that year.

Lewis had a solid—though not spectacular—first two years and never came close to living up to his monumental contract.

26. Alfonso Soriano, Chicago Cubs

The Deal: Eight years, $136 million.

Why it mattered: Soriano hasn't earned the dough, and the Cubs have been stuck with his contract since.

Soriano signed this deal coming off a 40-40 season and five straight seasons of 25 home runs and 90 RBI.

He hasn't knocked in more than 77 RBI once with the Cubs. For you advanced metrics folks out there, the highest oWAR (offensive wins above replacement) Soriano posted with the Cubs was 2.5 in 2007, a mark he had exceeded the previous five years.

In other words, Soriano's best years all came before the Cubs made him rich.

25. Andre Rison, Cleveland Browns

The Deal: Five years, $17 million.

Why it mattered: When Rison signed this deal in 1995, it made him the highest-paid receiver in NFL history.

He didn't live up to that billing, however: That season, he had career lows in receptions (47), yards (701), touchdowns (three), receptions per game (2.9) and yards per game (43.8). He was released at the end of the season.

There was a bad moon Rison indeed.

24. Cliff Lee, Philadelphia Phillies

The Deal: Five years, $120 million.

Why it mattered: Three reasons come to mind:

1. Lee was the prized jewel of this offseason's free-agency period and shocked everyone by passing over the Yankees and Rangers to return to the Phillies.

2. When Lee's salary increases to $25 million in 2013, it will be the most money a pitcher has ever made in a season (assuming another pitcher does not sign for a higher contract before then).

3. Lee is probably a front-runner for the NL CY Young, alongside the Dodgers' Clayton Kershaw this season (Roy Halladay being a close third). Oh, and take another look at that picture—he's been unhittable at times this season.

23. Kevin Brown, Los Angeles Dodgers

The Deal: Seven years, $105 million.

Why it mattered: Brown was baseball's first $100 million man, a fact that many in baseball were not pleased with.

Many general managers said the Dodgers acted irresponsibly, suggesting that they could have at least stopped at the $14 million plateau, which they zoomed past.

"I think this is dangerous for the competitive balance of the game," said Jim Bowden of the Cincinnati Reds. "The fact that Kevin Brown will make more in the next seven years than our whole team in the next four is not good."

Brown was solid during his tenure with the Dodgers (though injury-prone), compiling a 58-32 record in five seasons with a 2.83 ERA and a 1.1 WHIP. Then again, he was named in the Mitchell Report, so you can probably take those marks with a grain of salt.

22. Adrian Gonzalez and Carl Crawford, Boston Red Sox

The Deal: For Gonzalez (who was traded to Boston because he obviously was not going to re-sign with the Padres and immediately signed a contract extension), seven years and $154 million. For Crawford, seven years and $142 million.

Why it mattered: For starters, when the Red Sox made these moves, it was the second-largest amount of money ever spent on a pair of incoming players in MLB history.

Just how wise these investments are remains to be seen.

While Gonzalez has been phenomenal and is an AL MVP candidate, Crawford has been a bust this season. Still, Crawford seems too talented and dedicated to struggle in the future, and these two should lead the Sox to a World Series title (or more) in the upcoming years.

21. Albert Haynesworth, Washington Redskins

The Deal: Seven years, $100 million (with incentives—ha!—that could have maxed out the contract at $115 million).

Why it mattered: Hey hey hey, it's Fat Albert!

This 2009 deal blew up in Washington's face. Haynesworth only appeared in 20 out of a possible 32 games over two seasons and entered Mike Shanahan's doghouse in 2010 after coming to camp out of shape and disgruntled with his role in the team's new 3-4 scheme.

After recording 8.5 sacks in his last season with the Titans, Haynesworth only mustered 6.5 in his two seasons with the 'Skins.

Washington's leap of faith in signing Haynesworth was a historical one, as John Clayton of ESPN reported at the time:

"The deal, which was reached early Friday morning, includes an NFL-record $41 million in guarantees. During the first 13 months of the contract, Haynesworth will earn approximately $32 million."

Ladies and gentlemen, give it up for Daniel Snyder!

20. Tracy McGrady and Grant Hill, Orlando Magic

The Deal: McGrady and Hill signed identical seven-year, $92.8 million contracts in 2000.

Why it mattered: Four years after Shaq bolted for Los Angeles, the Magic thought they had added the cornerstones of a championship team.

However, Hill spent more time on the bench injured than he did on the court, and despite McGrady blossoming into a star, the team didn't win a playoff series in the four years he was there before being traded to the Rockets.

It was a disappointing period for Orlando, though the 2004 offseason ushered in the beginning of the Dwight Howard era.

19. Ilya Kovalchuk, New Jersey Devils

The Deal: Originally a 17-year, $102 million contract, changed to 15 years and $100 million after the original deal was disallowed by the NHL.

Why it mattered: It changed long-term contracts in the NHL. From ESPN:

"

A news release from the NHL and NHLPA said that "under the terms of the agreement, the new rules will apply only to long-term contracts, defined as those with terms of five years or longer, and only to contracts executed after Sept. 4, 2010. The new rules apply to contracts signed between now and the end of the CBA, as well as all contracts signed that begin in the 2012-13 season. The parties have agreed that the new rules do not automatically carry over into a new CBA."

In the future, the salary cap hit for any contract that is five years or more in length and takes a player to his 41st birthday or beyond will be determined by the average of the yearly salaries only until the year in which the player turns 40.

All remaining years in the deal after a player turns 41 will be recalculated based on the actual salary of those final years of the contract.

"

18. Deion Sanders, 49ers and Cowboys

The Deal: With the 49ers, a one-year deal in 1995 for $1 million. The following year with the Cowboys, a seven-year deal for $25 million.

Why it mattered: Sanders helped the 49ers and Steve Young win the Super Bowl in 1995.

The next year, he helped the Cowboys win their third Super Bowl in four years.

The flashy Hall of Famer is the perfect example of getting instant return on your investment.

17. Bobby Bonilla, New York Mets

The Deal: First with the Mets in 1991 at five years for $29 million, then later with the Marlins in 1996 at four years for $23.3 million.

Why it mattered: The Mets owe him $1.19 million a year for the next 25 years!

Yes, you read that correctly.

The first contract was bad enough, as Bonilla was a major disappointment, the Mets stunk and he was eventually traded to Baltimore in 1995. After signing another sizable deal in 1996 with the Marlins, he was traded to the Dodgers in 1998 and eventually to the Mets in the following offseason.

The second stay was just as poor as the first. Bonilla wanted out of New York, and the Mets wanted to clear the $5.9 million they still owed him for 2000. The Mets proceeded to postpone the payments owed to Bonilla for 11 years, at an eight percent interest rate, thus ensuring that he will earn just under $30 million from 2011 to 2035.

For the entire (ridiculous) tale, check out the Wall Street Journal's article on the story.

16. Mike Hampton, Colorado Rockies

The Deal: Eight years, $121 million

Why it mattered: Remember when it was assumed that no pitchers could succeed at Coors Field? Remember when the Rockies tried to dispel that notion by giving huge money to pitchers Mike Hampton and Denny Neagle (five years, $55 million) in 2001?

Yeah, that didn't work out so well.

Hampton only spent two years in Colorado, compiling a dismal 21-28 record with a 5.75 ERA and a 1.67 WHIP.

Ouch.

Neagle wasn't any better, lasting only two complete seasons himself (and a fraction of a third), finishing with a 19-23 record, a 5.57 ERA and a 1.47 WHIP.

15. Ichiro Suzuki, Seattle Mariners

The Deal: Three years, $27.125 million (including a $13.125 million posting fee).

Why it mattered: The first Japanese position player in the U.S. turned out to be one of the best signings in MLB history after Seattle signed Ichiro in 2001.

All he did that year was win both the Rookie of the Year and MVP awards en route to accumulating 2,407 hits, 1,120 runs, 420 stolen bases, a .326 batting average and a .377 OBP over 11 seasons and counting.

14. Manny Ramirez, Boston Red Sox

The Deal: Eight years, $160 million.

Why it mattered: They were the best of times—Manny led the Sox to two World Series titles while hitting .312 with 274 homers and 868 RBI during his stay in Boston—and they occasionally were the worst of times, such as when the Sox were so fed up with Manny that they put him on waivers, or when they finally traded him to the Dodgers in 2008.

Mostly, though, Manny being Manny translated into the Red Sox being champions.

13. CC Sabathia and Mark Teixeira, New York Yankees

(Pictured: $667 million in contracts)

The Deal: For Sabathia, seven years and $161 million. For Teixeira, eight years and $180 million.

Why it mattered: The Evil Empire strikes again!

Not only did Sabathia receive the largest contract for a pitcher in MLB history in 2009, but in that same offseason, the Yankees gave Teixeira what currently resides as the fifth-largest contract in MLB history.

To truly put this into perspective, the $55.5 million these two made this year is more than the payrolls of six MLB teams! (Those six being Kansas City, Tampa Bay, Pittsburgh, San Diego, Cleveland and Arizona.)

As much as you could possibly get your money's worth in this situation, the Yankees have: Sabathia and Teixeira have remained superstars, helping lead the Yankees to a World Series title in 2009.

12. Catfish Hunter, New York Yankees

The Deal: Five years, $3.35 million.

Why it mattered: Hunter was essentially baseball's first big-name free agent in 1975, and after winning three consecutive titles with Oakland, he didn't disappoint in New York.

In his five seasons with the Yankees, Hunter went 63-53 with a 3.58 ERA and was splendid in both 1975 and 1976, throwing—and here comes the time warp—a remarkable 30 complete games in 1975 (tops in the American League).

Let's review the season he had in 1975, the year he finished second in the Cy Young voting to Jim Palmer: 23-14 (tied for first in wins in AL), 2.58 ERA (second-best ERA in AL), 177 strikeouts (seventh in AL), 1.009 WHIP (best in AL), seven shutouts (second in AL) and 328 innings pitched (most in AL).

Had it not been for a remarkable year by the Orioles' Palmer, Hunter would have been the easy choice for the American League Cy Young Award.

11. Andy Messersmith, Atlanta Braves

The Deal: Three years, $1 million.

Why it mattered: While Catfish Hunter became the first free agent after A's owner Charlie Finley did not properly meet his contract—and Curt Flood's reserve clause battle got the conversation started—free agency didn't become institutionalized until it was granted to Andy Messersmith and Dave McNally in 1975 (although McNally retired).

Messersmith's motivation wasn't purely financial in nature (read the entire article—it goes into far more depth than I can here):

"

"It was less of an economic issue at the time than a fight for the right to have control over your own destiny," Messersmith told The Sporting News more than 10 years later. "It was a matter of being tired of going in to negotiate a contract and hearing the owners say, 'OK, here's what you're getting. Tough luck.'"

"

Ballplayers ever since are grateful that "tough luck" wasn't good enough for Messersmith.

10. Reggie White, Green Bay Packers

The Deal: Four years, $17 million.

Why it mattered: ESPN is more concise than I would be.

Three months after a collective bargaining agreement was reached that brought free agency to the NFL, White, the most coveted player available, stunned the football world and signed with the Packers for four years and $17 million.

On the field, White's contributions over the next six seasons far exceeded the investment.

He became the anchor of a defense that ranked No. 1 in the league when the Packers won Super Bowl XXXI. With his signature pass-rush techniques, he registered 76.5 sacks and retired—after a final season in Carolina in 2000—as the game's all-time sack leader.

With the possible exception of Brian Dawkins, there has never been a sadder departure in Eagles history than when the team decided against re-signing White in 1993.

9. Drew Brees

The Deal: Six years, $60 million.

Why it mattered: Generally in these types of deals, it is the team that releases a player like Brees that will suffer the consequences.

Not so in this case, as the Chargers accurately predicted in 2006 that Philip Rivers would be an elite quarterback.

No, the team in this case that is still kicking itself to this day is the Miami Dolphins, who were Brees' first choice when he became a free agent.

But Miami was concerned with his shoulder and ended up signing Daunte Culpepper (bust). Brees joined Sean Payton in New Orleans, where the two have won a Super Bowl, while Miami is currently taking its chances with Chad Henne.

Yup, Chad Henne. Miami is wishing they saw in Brees what the Saints did right about now, that much is for sure.

8. Randy Johnson, Arizona Diamondbacks

The Deal: Four years, $53 million.

Why it mattered: Johnson won the Cy Young Award four straight times over the course of this deal, along with leading the Diamondbacks (along with Curt Schilling) to a World Series title in 2001.

Methinks fans of the Diamondbacks found him to be worth every penny.

Only one other player in MLB history has ever won four straight Cy Youngs, and he happens to appear on the next slide.

7. Greg Maddux, Atlanta Braves

The Deal: Five years, $28 million.

Why it mattered: For one, Maddux could have gotten a $34 million deal from the Yankees, which he turned down.

A $28 million steal?

Considering that Maddux would go on to win the Cy Young Award in the first three years of this deal (1993-95) and would help Atlanta to its 1995 World Series title, yeah, I'd say it was a steal.

For the record, Maddux won four straight Cy Young Awards, also claiming the 1992 award while with the Cubs. He joins Johnson as the only pitchers in history to accomplish this feat.

6. Reggie Jackson, New York Yankees

The Deal: Five years, $2.9 million

Why it mattered: Can you say Mr. October?

After signing with the Yankees in 1977, Jackson famously smacked three home runs in Game 6 of the World Series, leading to the first of two consecutive titles for the Bronx Bombers.

Though his relationship with manager Billy Martin was tumultuous, Jackson was undeniably the missing power bat the Yankees lineup desperately needed.

5. Kobe Bryant, Los Angeles Lakers

The Deal: Seven years, $136.4 million

Why it mattered: Kobe flirted with the free-agent market in 2004, allegedly coming close to signing with the Clippers.

For his sake, and that of the Lakers, it's probably best that he didn't. Kobe has since won two more championships with the Lakers, pushing his total to five.

The Clippers? Well, they're still the Clippers.

4. Shaquille O'Neal, Los Angeles Lakers

The Deal: Seven years, $120 million.

Why it mattered: Just ask Orlando.

While Shaq went on to win three NBA titles, three NBA Finals MVP awards and one regular season MVP award, the Magic never amounted to much more than a playoff team that struggled to get out of the first round.

Dwight Howard revitalized the organization when he was drafted in 2004, but by that point, Magic fans everywhere were surely jealous of the Lakers and their three-peat with Shaq.

3. Alex Rodriguez, Texas Rangers

The Deal: 10 years, $252 million.

Why it mattered: Many reasons. Here are a few, as laid out by Jason Reid of the Los Angeles Times at the time of the signing:

"The deal surpassed the previous U.S. athlete record for total value and average annual salary—the six-year, $126-million contract Kevin Garnett signed with the NBA's Minnesota Timberwolves in 1997."

Which obviously made it controversial within baseball circles.

News of Rodriguez's contract was not well received by baseball officials concerned about payroll disparity and dizzying amounts of spending.

The Rangers were criticized for being the first sports team to break the $200 million barrier, but they got the player they coveted.

To his credit, Rodriguez played up to expectations in the three years he remained in Texas, winning an MVP his last year there and finishing as the runner-up the year before. He averaged a .305 batting average, 52 home runs and 131 RBI in his three seasons with the team, or a total WAR of 23.9 for the advanced metrics folks out there.

Oh, and A-Rod's current contract with the Yankees (10 years, $275 million) is even larger than the one he signed with the Rangers.

Jealous yet?

2. Barry Bonds, San Francisco Giants

The Deal: Six years, $43 million.

Why it mattered: Ask a Pirates fan.

While Bonds won five MVP awards for the Giants and (controversially) broke Hank Aaron's all-time home run record, the Pirates have suffered through 18 straight losing seasons since his departure. Keep in mind that this was a team that won three straight division titles from 1990-92.

Ouch.

1. LeBron James, Miami Heat

The Deal (sign-and-trade with Cleveland): Six years, $110.1 million. Chris Bosh signed an identical deal, but we all know this was all about LeBron.

Why it mattered: Oh, it was only the largest free-agency spectacle in American sports history, that's all.

Teams had spent the previous two seasons clearing cap space for the chance to sign James (and other free-agents-to-be such as Bosh, Dwyane Wade, Amar'e Stoudemire and Carlos Boozer).

And then James went on national television and The Decision happened; the Heat retained Wade along with the additions of James and Bosh, while everyone outside of Miami instantly despised James and the Heat. James predicted a bunch of championships, and everyone became huge Dirk Nowitzki fans during the NBA Finals.

The whole thing turned James from a generally beloved superstar into a widely despised superstar (you're off the hook, Kobe). Paired with an amazing postseason that saw a talented young crop of players seize control of the league, it all turned out to be really good theater for the NBA.

It's just a shame the lockout might ruin all of that.

Be sure to hit me up on Twitter (@TRappaRT) along with the entire B/R Swagger team (@BR_Swagger).