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MLB Free Agency: 50 Greatest Players Ever to Hit the Free Agent Market

Dan TylickiAnalyst IDecember 4, 2016

MLB Free Agency: 50 Greatest Players Ever to Hit the Free Agent Market

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    MLB Free Agency has not been around all that long compared to the history of baseball, as it has only been 35 years since the first free agents made their money. Since then, contracts have shot up, and players make far more money than anyone thought imaginable.

    Larger contracts and more players entering free agency means more teams trying to grab the best players as well, and some of the players are so good that most teams are going to at least look at them as options.

    The following are the top 50 free agents ever, rated by player quality, demand, and most importantly, how good they were at the time of their free agency.

50. Darryl Kile

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    In eight years as a starter for the Houston Astros, Darryl Kile turned into a reliable starter. He went 19-7 with a 2.57 ERA in 1997, and was naturally heavily pursued as a free agent that offseason.

    Houston, Arizona, San Diego, and others made offers, but in the end, the Colorado Rockies got him for three years and $22 million. They forgot that pitchers fall apart in Colorado, so he was traded to St. Louis, where he again showed great consistency.

49. Ichiro Suzuki

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    The biggest free agent battle involving the posting system was actually not Ichiro. He was, however, the first, and there were a huge number of teams that bid on the Japanese star.

    The Cleveland Indians tried to acquire him to replace Manny Ramirez, and the Boston Red Sox took a shot at him, but the Seattle Mariners won with a bid of over $13 million, far higher than what was expected.

    That being said, the move has more than paid dividends for them.

48. Jack Morris

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    When Jack Morris was done in Detroit at 35, the Twins signed him to a one-year deal in 1991, where he went on to win a World Series and go 18-12. As a result, he was suddenly a highly sought-after free agent.

    Despite being at home in Minnesota and despite his age, he got offers from multiple teams, and ended up with the Blue Jays for two years and over $10 million. As a result, Toronto won two World Series titles, though Morris was done by then.

47. Mark Langston

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    Mark Langston started his career with the Mariners before going 12-9 with a 2.39 in half a season for the Montreal Expos. As a result, he was a big target in the 1989 offseason.

    The New York Yankees, Los Angeles Dodgers, and California Angels all offered him five years, but the Angels' $16 million offer won him over, and for a very short time it was the highest contract in history. Langston was a key part of the rotation for many years after.

46. Bobby Grich

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    In 1976, the first group of free agents broke free, and perhaps the cream of that first class was infielder Bobby Grich. He won four Gold Gloves and had three All-Star bids with Baltimore.

    While many teams were interested, the California Angels gave him a five-year, $1.35 million deal, which was huge at the time. He improved offensively with the Angels but did not win another Gold Glove, and given how new free agency was, it's tough to evaluate this deal in hindsight.

45. Rich Gossage

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    Relievers have not necessarily been huge free-agent pickups, but a few end up being in high demand. One of the first was Rich Gossage, who had a great year in 1977 with Pittsburgh and was ready to earn a long-term deal.

    The Yankees gave him just that, signing him for six years in what ended up being a great move. His six excellent seasons in New York as a closer is likely what helped him get in the Hall of Fame more than anything else.

44. Rollie Fingers

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    From one great mustache on a reliever to another, Rollie Fingers was a great reliever for the Oakland Athletics, coming close to a Cy Young win before opting for free agency in 1976.

    He ended up signing with the San Diego Padres for six years and $1.6 million. He played four years in San Diego and was traded to the Brewers, so naturally, the next season he was declared MVP.

43. Mark Davis

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    Tired of relievers yet? How about that he won the Cy Young Award, then became a free agent? That's exactly what Mark Davis did in 1989 for the Padres.

    After he declared free agency late, the Padres shrugged him off, though they were one of the few. He signed with the Kansas City Royals for three years, and there's no question that the move was a bust.

42. Tim Raines

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    Tim Raines was a perennial All-Star for the Montreal Expos, and was a sure thing to steal bases through 1986, when he opted for free agency after a career year, winning his only Silver Slugger Award.

    Owner collusion led to low demand, though he did receive an offer from the Padres. On May 1, when he could finally negotiate with his former team, he did exactly that, and quickly re-signed with the Expos.

    He was projected as a premier signing that year had free agency not been trouble under Commissioner Peter Ueberroth.

41. Andres Galarraga

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    Andres Galarraga, the first baseman primarily for the Expos, put up huge numbers for the Colorado Rockies in their first five years of existence. Thanks to placing high in MVP voting those years, he was a free agent who was looked at even though he was 36.

    The Atlanta Braves had traded Fred McGriff and made an opening for him, signing him to a three-year, $24.75-million deal. He had two good years for Atlanta, but had he not missed the 1999 season, the deal may have looked better.

40. Bernie Williams

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    One of the key Yankees during their run in the late 1990s, it's hard to picture Bernie Williams as a free agent, but after a career year in 1998, that's what Williams opted to do.

    After being the subject of a Red Sox-Yankees bidding war, the Yankees won out, giving him $87.5 million. He went on to finish his career with the Yankees in 2006.

39. Bruce Sutter

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    After nine years with the Chicago Cubs and St. Louis Cardinals, Bruce Sutter was coming off one of his best seasons in 1984, where he had a 1.54 ERA and finished third in Cy Young voting.

    While demand was high, the Atlanta Braves moved quickly, and after a back-and-forth between both sides, Sutter signed for six years and $10 million in what ended up being a bad deal for the Braves.

38. Kirk Gibson

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    Kirk Gibson is now known as the manager turning the Arizona Diamondbacks around, but for a long time he was known for his performance in 1988, winning MVP and having the well-known walk-off home run in the World Series.

    The year before, he had become a free agent after a solid 1987 season with Detroit. He had offers from the Tigers and Padres, but in the end agreed to a deal with the Los Angeles Dodgers. The three-year, $4.5 million deal was definitely a great one for them.

37. David Cone

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    David Cone was a free agent a few good times in his career. He signed with the Royals in 1992 and ended up winning the Cy Young Award in 1994. A year later, after splitting time with Toronto and New York, he opted for free agency.

    The Baltimore Orioles came close to acquiring him, and the Florida Marlins considered signing him, but in the end the Yankees kept him, signing him for three years and $19.5 million, which paid dividends when he won 20 games in 1998.

36. Pete Rose

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    Pete Rose became a free agent in 1978, and while he had continuous success with the Cincinnati Reds, he was 37 and no one knew how much he had left in the tank. Still, five teams wanted to acquire him.

    The Pirates, Braves, Cardinals, and Royals all made offers, but in the end, the Phillies got him for four years and $3 million. They went on to win the World Series in 1980, and after his contract was done, he was just about at 4,000 hits.

35. Mark McGwire

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    Had McGwire been a free agent in 1997 or 1998, there's no question he would be near the top of this list.

    However, his free agent season came in 1992, where he had a great year, but was overshadowed by a certain other power hitter who broke his home run record.

    He seemingly came close to leaving Oakland, especially after Jose Canseco was traded, but in late December, he re-signed with them for five years and $28 million. The rest is history.

34. Carlton Fisk

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    Free agency was still relatively young in 1980, but after an All-Star appearance and overall solid numbers year after year for the Boston Red Sox, Fisk became a free agent that season after arbitration failed.

    The Boston Red Sox and Toronto Blue Jays pushed hard to acquire Fisk, and in the end, he signed with the Chicago White Sox for five years and $2.9 million.

    He spent 13 more years with the White Sox and was a staple of their team.

33. Paul Molitor

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    It's not too often that a 15-year veteran and future Hall of Famer enters free agency, but that's precisely what Paul Molitor did. After having multiple great seasons for the Milwaukee Brewers, he became a free agent in 1992.

    Once Molitor rejected the offers by the Brewers, the floodgates opened on him, and he cited moving closer to home in Minnesota. In the end, Toronto signed him to a three-year deal, where he remained a strong presence and nearly won MVP in 1993.

32. Andy Pettitte

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    Andy Pettitte was a great nine-season veteran of the New York Yankees who elected for free agency in 2003. Like Bernie Williams, it seemed like he would probably stay with the Yankees.

    The Yankees offered three years and $30 million, but the Houston Astros offered a big deal as well.

    Surprisingly, a bidding war did not really emerge, and Pettitte ended up with Houston for three years alongside Roger Clemens.

31. Gary Sheffield

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    During the Steroid Era, age was mostly disregarded, and players who were great power hitters were picked up for big money even if they were 35. Gary Sheffield was one of these in 2003 after two great years with Atlanta.

    Despite testifying in the BALCO case during the free agency period, the New York Yankees pushed to acquire Sheffield big time, to the point where other offers were not really noted.

    He played with the Yankees for three years, and was highly productive two of those years.

30. Prince Fielder

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    Prince Fielder would likely be a lot higher on the list, but his free agency is somewhat overshadowed by that of Albert Pujols. Either way, the 27-year old is being looked at by many teams, including the Cubs, Mariners and others.

    Should a bidding war emerge after Pujols signs somewhere, he could deserve to jump higher on here.

29. Wade Boggs

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    While 1992 is quickly being established as the best free agent class just by some of the players on this list, the Boston Red Sox and New York Yankees know it for one man: Wade Boggs, who moved on from Boston after 11 years.

    The Los Angeles Dodgers and New York Yankees both gave him offers, and as both sides drew closer, it became evident Boggs would sign with New York. He did just that, signing with them for five years and drawing the ire of Boston.

28. Kevin Brown

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    Kevin Brown was a pitcher who didn't really get it going until 30 except for one season, but from 1995 to 1997, he was a premier pitcher. After an 18-7 season in 1998, Brown went into free agency to finally get that big payday.

    The Baltimore Orioles took a shot at Brown, as did the Atlanta Braves, but in the end the Dodgers gave Brown a seven-year, $105 million deal. The record contract ended up being too long, but it was far from the worst deal, as Brown pitched well most of the five years he was in L.A.

27. Daisuke Matsuzaka

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    In hindsight, it seems odd that Daisuke Matsuzaka was the Japanese prospect who garnered way more attention than any other one in the posting system, but this was the case in 2006, after a successful career with the Seibu Lions, perhaps due to his agent being Scott Boras.

    The Texas Rangers, New York Mets and New York Yankees bid on him, but the Boston Red Sox crushed them with a bid of over $50 million. He has a year left on his deal, but he has arguably been a bust with how much hype there was on his signing.

26. Mike Hampton

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    Mike Hampton is the poster child for teams to beware of signing a player to a big deal when they had one great year out of nowhere. In 1999, Hampton had that year, going 22-4 with a 2.90 ERA. He was traded to the Mets and had another very good year, and entered free agency in 2000.

    The Chicago Cubs and Boston Red Sox tried to sign him, but the Colorado Rockies ended up winning, signing him for way too many years and way too much money en route to having the all-time bust. It pays to have that one year on your resume, it seems.

25. Andre Dawson

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    For 11 years, Andre Dawson was a staple of the Montreal Expos, regularly making the All-Star team and putting up great numbers. In 1986, the 31-year-old became a free agent after declaring his time in Montreal was done.

    Dawson was one of the few to break through owner collusion stopping free agency in the mid-1980s, signing with the Chicago Cubs for less money than Montreal offered.

    It worked well, since Dawson won the MVP that year and got a much bigger deal from Chicago after that.

24. Adrian Beltre

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    Third baseman Adrian Beltre had a career year in 2004, hitting 48 home runs, batting .334, and nearly winning the MVP. As a result of that as well as his age (25), he was in high demand.

    The Dodgers tried to re-sign him, and others tried to acquire him, but the Seattle Mariners ended up signing Beltre to a five-year, $64 million deal. He was still a good power hitter, but there was no question that Seattle overpaid.

23. Barry Zito

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    For as much flack as Barry Zito gets, he was a very good pitcher for Oakland for seven years. None of those seasons were bad, and he won a Cy Young Award in 2003. As a result, when he became a free agent in 2006, many teams tried to sign him.

    The Mets and Rangers were among the teams trying to acquire him, but they were beaten out by the San Francisco Giants. The expensive seven-year deal is, to put it simply, one Giants fans do not like to talk about.

22. Jim Thome

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    Jim Thome was a staunch veteran of the Cleveland Indians for 12 seasons, and in 2002, he had one of his best seasons yet. He finished seventh in MVP voting, and hit .304 with 52 HR and led the league in walks.

    Many teams tried to take hold of him, and the Indians were definitely at the front of that charge. The Phillies ended up signing him for six years and $85 million. He still had great power, but that's about when his average started falling.

21. Vladimir Guerrero

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    Not unlike Andre Dawson, Vladimir Guerrero was a big-time power hitter for the Montreal Expos, and in the early 2000s was a perennial All-Star who could hit for power and average.

    After becoming a free agent in 2003, the Baltimore Orioles and New York Yankees came out firing and wanted the slugger badly. In the end, though, the Angels got him for five years and $70 million, and Guerrero went on to be MVP the next year.

20. Albert Belle

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    For those wondering where the big power hitters of the '90s are, a bunch are on their way. Leading off that pack is Albert Belle, the left fielder who was the leader of the Cleveland Indians for four seasons as a power hitter before becoming a free agent in 1996.

    The Indians made a big offer to him, as did the Florida Marlins, but the Chicago White Sox made a bigger one, signing him with a clause stating that he remain one of the highest paid players in baseball. That's likely why he was only in Chicago for two years.

19. Mo Vaughn

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    Mo Vaughn, first baseman of the Boston Red Sox, was a big guy with a bigger bat, winning MVP in 1995 and having multiple great power seasons. In 1998, after hitting .337, he became a free agent.

    After rejecting the Red Sox offer, the Angels gave him a six-year, $72 million deal. After a bidding war, the deal became $80 million, which he signed, and while he was solid the first two years, he fell apart after that.

18. Bobby Bonilla

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    Bobby Bonilla and Barry Bonds formed a dynamic one-two punch in Pittsburgh in 1990 and 1991, with Bonilla nearly winning two straight MVPs. After 1991, Bonilla became a free agent, and was the star of that crop.

    The Phillies, Pirates and Angels were all interested, but the Mets signed him to a five-year deal worth $29 million. The move ended up being so bad in hindsight that the Mets are literally still paying for it.

17. Roger Clemens

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    Despite all the money Roger Clemens made, he could have made more had he become a free agent after his best seasons.

    When he became a free agent in 1996, he was a hot commodity who could still lead in strikeouts, but he wasn't the premier pitcher he used to be the past couple years.

    Still, he was Roger Clemens, so of course teams tried to acquire him, shrugging off both the Red Sox and Yankees with their big offers to pitch for the Toronto Blue Jays, signing a three-year, $24.75 million contract.

    In both seasons, with Toronto he won the Cy Young Award.

16. Mark Teixeira

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    Mark Teixeira's stats would not make you think he is nearly a top-15 free agent, but when he became a free agent in 2008, teams saw both his great all-around numbers and how he seemed to make others better, so demand was high.

    After the Orioles, Red Sox, and others tried to acquire him, he signed with the Yankees for eight years and $180 million. He has continued his power and defense in three years with New York so far, even if his average has taken a hit.

15. Nolan Ryan

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    Nolan Ryan was a pitcher who had a bit of hard luck in the win-loss column, but consistently won strikeout title after strikeout title and kept his ERA low, so when he became a free agent in 1979, everyone wanted him.

    While many teams tried to acquire him, the Houston Astros quickly gave him an offer he couldn't refuse at four years and $4 million, making him the first player to crack a million per season. He rewarded them with a couple ERA league leads, and of course plenty of strikeouts.

14. Rick Sutcliffe

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    Rick Sutcliffe started his career as a solid pitcher for the Dodgers and Indians, but when he was traded to the Chicago Cubs in 1984, he had one of the best seasons ever, going 16-1 in 20 games and winning the Cy Young.

    When he became a free agent that year, demand was huge. The Padres, Royals, and Braves made offers, and many other teams expressed interest. After bouncing around his options, Sutcliffe stayed with the Cubs, and had several more good seasons with them, though nothing like 1984.

13. Mike Mussina

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    In 10 years with the Orioles, Mike Mussina was clearly up there in Cy Young discussion, having great season after great season, even though he did not win the award. As a result, when he was a free agent in 2000, he was a hot commodity.

    Surprisingly, he was the third-best free agent that year, but the Yankees focused on him first and foremost, more so than the Mets and others who tried to snag him.

    The end result was a six-year deal worth $88.5 million, and he remained with the Yankees through 2008.

12. Reggie Jackson

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    in 1976, during the advent of free agency, teams weren't really sure of what would happen. They did know one thing, though. Reggie Jackson was available, and when an MVP is available, you try to acquire him.

    That is exactly what happened, with the Expos and Yankees being the most aggressive teams. He signed with the Yankees, and we all know how his time was with them.

11. Cliff Lee

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    Just missing out on the top 10 is Cliff Lee. After many seasons of varied success with the Cleveland Indians, he came out of nowhere to go 22-3 and win the Cy Young in 2008. Two years later, after a great playoff run, he entered free agency, and was the best of last year's class.

    Everyone presumed he would sign with the Yankees or the Rangers, but the Phillies came out of nowhere and signed him for five years and $120 million. He was great in his first season with Philadelphia, so it's so far so good for them.

10. Catfish Hunter

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    Catfish Hunter is a very special case on this list. He became a free agent in 1974, and if you read the other slides, you know free agency did not officially start until 1976. How did the Cy Young winner enter it?

    This is the result of Charlie Finley failing to pay Hunter $50,000 after the 1974 season, and he ended up a free agent due to the contract violation. Every team except the A's looked at him, and after many offers, he signed with the Yankees, playing his last five years with them.

9. Manny Ramirez

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    In seven years with the Cleveland Indians, Manny Ramirez established himself as a star, being able to hit .300 no problem, and hit 40 HR, 100 RBI, and was a perennial All-Star. When he joined free agency in 2000, he was a big target.

    I almost knocked him far down this list because contract demands were so high that only the Indians and Red Sox were really trying to acquire him. In the end, the Red Sox got him for $160 million, and the deal worked out on both sides.

8. Jason Giambi

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    Jason Giambi was able to fill in pretty quickly for the Oakland Athletics after they traded Mark McGwire. In seven seasons, he became a feared power hitter, won one MVP and should have won a second in 2001, the year he became a free agent.

    While demand was high, the Yankees were the first to go after him, and when they did, it seemed a foregone conclusion that they would sign him. They did just that, giving him a seven-year contract that kept him going even when he pretty much stopped producing.

7. Pedro Martinez

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    When Pedro Martinez became a free agent in 2004, it may have been a couple years later than ideal; imagine if he had been one in 2000. Still, after three Cy Young wins and four ERA title wins, everyone wanted him after his contract was up.

    There was talk that he would bolt for the Yankees among other teams, but in the end it was the Mets that signed him to a four-year deal. He was great the first year, but unfortunately that is when injuries began to take his toll, and he did not return to greatness.

6. Greg Maddux

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    When you have a 26-year old Cy Young winner entering free agency, it's obvious what the demand will be. Greg Maddux established himself as a star pitcher with the Cubs and was looking for his payday in 1992.

    The Yankees pushed hardest to acquire him, but in the end, Maddux signed with the Atlanta Braves for five years and $28 million, actually less than the Yankees' offer.

    He ended up leading the Braves' pitching dynasty in the 1990s and is a no-brainer for the Hall of Fame.

5. CC Sabathia

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    The workhorse of the Cleveland Indians rotation in the 2000s, CC Sabathia won a Cy Young and was traded to the Milwaukee Brewers in 2008. There, he had the best half-season in history by anyone not named Rick Sutcliffe, and then became a free agent.

    The Brewers tried to keep him, and many others expressed interest, but the Yankees weren't going to let this pitcher slip through. At six years and $161 million, it's a huge deal, but so far it's paid off, as he's clearly been the ace of the staff.

4. Alex Rodriguez

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    A 24-year old free agent is rare enough, but a 24-year old free agent coming off a near-MVP season that's sure to be a five-tool player for the next decade? Well, that's Alex Rodriguez. In 2000, after a great year in Seattle, he was ready to make some real money.

    When the Rangers gave him the richest contract ever at 10 years and $252 million, that said it all. He was later sent to the Yankees, and after leaving Seattle became a three-time MVP.

3. Randy Johnson

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    One of the greatest pitchers of all time, Randy Johnson was a surefire ace during his time in Seattle, winning a Cy Young Award. He was traded to Houston in 1998, where he went 10-1 with a 1.28 ERA and became a free agent after the season.

    As perhaps the best pitching free agent ever, the Astros tried to re-sign him, and many others wanted him as their staff's ace. The expansion Arizona Diamondbacks were able to grab him for four years and $52.4 million, and he repaid them by earning four Cy Young Awards in a row.

2. Barry Bonds

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    Before Barry Bonds was a feared slugger at the height of the steroid era, he was the best five-tool player in all of baseball. He won two MVP Awards with the Pittsburgh Pirates before becoming a free agent in 1992, and came close to winning a third.

    The Yankees offered him a huge deal, though he was out of the price range for most teams. The Giants were one of the few that could afford him, and he signed for six years and $43.75 million. Five MVPs and the home run title later, Bonds is certainly the most controversial modern figure in baseball.

1. Albert Pujols

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    I wasn't sure where to place Albert Pujols on this list originally. After giving it some thought, though, he really does deserve to be first. He has been a perennial MVP candidate for a decade, has won three, and is the closest to a sure thing we've ever seen.

    None of the other 49 players on this list can say that about their careers when they were free agents. Pujols stands alone as a player who is naturally in high demand, because this type of greatness usually does not enter free agency in its prime.

    Suffice to say, Albert Pujols is the greatest free agent baseball has seen.

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