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Posted: Thursday May 15, 2008 11:06AM; Updated: Thursday May 15, 2008 3:16PM
Jon Heyman Jon Heyman >

What a deal! Ranking the best free-agent signings in history

Story Highlights
  • For altering the Red Sox fortunes and his own, David Ortiz tops the list
  • Adding some new names to the worst free-agent signings list
  • Are more changes on the way in Cincinnati?
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David Ortiz
David Ortiz kickstarted his career after arriving in Boston in 2003.
Brad Mangin/SI

Not all free-agent contracts are as bad as Mike Hampton's or Barry Zito's. Some actually work out. So now, a few weeks after I listed the 13 worst free-agent contracts of all time (and, as I was reminded, omitted some real doozies), I will pay homage to history's big signings that paid off.

There actually have been a lot of tremendous, even franchise-transforming free-agent signings. And while many of the best occurred in the 1970s, which was free agency's infancy, and 1993 was the single best free-agent season (Barry Bonds, Greg Maddux, Jimmy Key, Paul Molitor, and David Cone all inked large deals with new teams), my choice for best signing ever goes to a much more recent one: David Ortiz, by the Red Sox in 2003 for $1.25 million. Almost immediately, Big Papi became a franchise-altering slugger who also transformed himself, from a bust to one of the game's two or three best -- and most clutch -- sluggers.

In six years (including this one) in Boston, Ortiz has hit 215 home runs, a far cry from to the 58 he hit in six years in Minnesota. Since arriving in Beantown, he's been close to the equal of Manny Ramirez, No. 5 on my list, at less than one percent of the initial investment ($160 million) for Ramirez.

Without further ado, my best free-agent signings ever (the year listed is the first with the new team) ...

1. David Ortiz, Red Sox designated hitter, 2003; $1.25 million, one year. When Ortiz was signed just weeks before the start of spring training, newly hired and 29-year-old Red Sox GM Theo Epstein claimed that one day Ortiz could emerge as a key middle-of-the-order hitter. Some might have scoffed, but as it turns out, Ortiz has done much more than that, and is probably a Hall of Famer based only on the half a career he's spent in Boston. Later, the Red Sox signed Ortiz to two more team-friendly deals (though not nearly this team friendly).

2. Reggie Jackson, Yankees outfielder, 1977; $2.9 million, five years. It sounded like a lot of money at the time. But never has a free agent made such an impression in his very first year. The three home runs in the clinching Game 6 of the World Series were worth 10 times the entire contract, if not more. Not to mention all the other headlines Jackson made in his triumphant and newsworthy stay.

3. Greg Maddux, Braves pitcher, 1993; $28 million, five years. Maddux could have gotten at least $34 million, and maybe more, from the Yankees. Instead, he helped the Braves roll to 11 straight division titles. The Cy Young awards he won in each of his first three years there made this contract an all-time bargain and helped earn him a hefty raise when it expired.

4. Barry Bonds, Giants outfielder, 1993; $43.75 million, six years. The deal was a record at the time, but Bonds proved to be worth every penny, winning the NL MVP award in his debut season in San Francisco. Even before he and his head got so big, he was the best there was. He wound up staying 15 years, breaking baseball's biggest record, making everyone a lot of money, and eventually upsetting enough folks that no one wanted to employ him. But that part came later. A lot later.

5. Manny Ramirez, Red Sox outfielder, 2001; $160 million, eight years. Three years into this deal, the Red Sox put Ramirez on waivers, offering him -- and the contract -- to all 30 teams and asking nothing in return. There were no takers. Good thing, too. Ramirez cut back on his goofy ways but kept hitting and helped the team that never won to two World Series titles. The Red Sox also hold two option years for 2009 and 2010 at $20 million apiece, plus some deferred monies make this contract worth somewhat less than $160 million.

6. Don Baylor, Angels designated hitter, 1977; $1.6 million, six years. In Baylor's excellent career, some of his best years were in Anaheim, especially 1979 when he was MVP and led the Angels to their first AL West title.

7. Catfish Hunter, Yankees pitcher, 1975; $3.35 million, five years. He was baseball's first big-time free agent, and the Southerner from Hereford, N.C., delivered big-time in the Bronx. He left Oakland after winning three straight World Series titles, then helped the Yankees win two more titles (with his buddy Reggie). A gutsy performer who eventually threw until his arm fell off but still made the Hall.

8. Carlton Fisk, White Sox catcher, 1981; $2.9 million, five years. This New Hampshire native shocked a lot of folks by leaving Boston at age 33. And shocked even more by playing another 13 years, fashioning a Hall of Fame career by doing as much in his second decade in the bigs as his first. Trivia: his agent for the deal, Jerry Kapstein, now serves in the Red Sox front office.

9. Ichiro Suzuki, Mariners outfielder, 2001; $27.125 million, three years (including. $13.125 million posting fee). Tremendous all-around talent who's probably unappreciated in the United States since he's tucked away in the Northwest. Nobody combines a great arm, great legs and hitting ability like him. A Hall of Famer once he gets his 10 years in.

10. Nolan Ryan, Astros starter, 1980; $3 million, three years. When he signed this deal in the early '80s to play for his hometown team, he talked like it might be his last one. Who knew he'd pitch another decade after this deal expired?

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