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Home
National
Sports The 12 best free-agent deals in MLB history

The 12 best free-agent deals in MLB history

75756A5E-120A-4932-810C-2FD980DB785E
By Tim Kelly, Audacy Sports
Updated on

What are the greatest free-agent signings in the history of Major League Baseball? Tim Kelly of Audacy Sports examines the 12 best in this gallery.

Carlos Beltran
Carlos Beltran signed a megadeal with the Mets. Photo credit (Al Bello/Getty Images)

12. Carlos Beltrán - 7-Year/$119 Million Deal With New York Mets Ahead of 2005 Season

Beltrán went on one of the great postseason tears in MLB history with the Houston Astros in 2004, hitting .435 with eight home runs and 14 RBIs in 46 at-bats. This earned Beltrán a lucrative deal with the Mets. During the first six seasons of the deal, Beltrán homered 134 times and drove in 493 runs, excellent individual production, even if it didn't lead to the Mets having the team success they desired during that period. During the final season of Beltrán's deal, the Mets traded him to the San Francisco Giants, netting Zack Wheeler in return for a rental.

Mike Mussina
Mike Mussina left the Orioles to sign with the Yankees. Photo credit (Al Bello /Allsport)

11. Mike Mussina - 6-Year/$88.5 Million Deal With New York Yankees Ahead of 2001 Season

The Yankees got a front-row view of Mussina for a decade in Baltimore, so they pounced when they had the chance to sign him after the 2000 season. Mussina was never the best pitcher in baseball during eight seasons with the Yankees, but he cemented himself as a Hall of Famer by posting a 3.50 FIP in 249 games for the team.

CC Sabathia
CC Sabathia signed with Yankees ahead of the 2009 season. Photo credit (Nick Laham/Getty Images)

10. CC Sabathia - 7-Year/$161 Million Deal With New York Yankees Ahead of 2009 Season

Sabathia was traded from Cleveland to the Milwaukee Brewers ahead of the 2008 trade deadline, and went on one of the great runs in MLB history, going 11-2 with 1.65 ERA in 17 starts after being acquired. This earned Sabathia a massive deal with the Yankees, who were coming off their first year not reaching the postseason since 1994. Sabathia - who joined the Yankees in the same offseason as A.J. Burnett and Mark Teixeira - would guide the franchise to their 27th World Series title in his first season with the team, ultimately spending 11 seasons in the Bronx.

Reggie Jackson
Reggie Jackson signed with the Yankees. Photo credit (Dick Raphael/USA Today)

9. Reggie Jackson - 5-Year/$2.96 Million Deal With New York Yankees Ahead of 1977 Season

Jackson spent double the time in Oakland as he did with the Yankees, but it was in New York where he became "Mr. October." Signing for what is now a laughable amount, Jackson made five All-Star teams in his five seasons with the Yankees, swatting 144 home runs over the same period. The Yankees won World Series titles in 1977 and 1978, with Jackson homering seven times in the 1977 World Series alone.

Adrian Beltre
Adrian Beltre signed with the Rangers ahead of the 2011 season. Photo credit (Rob Carr/Getty Images)

8. Adrián Beltré - 5-Year/$80 Million Deal With Texas Rangers Ahead of 2011 Season

Beltré is considered one of the greatest third basemen in MLB history now, but he didn't necessarily seem on that path at the time of his 30th birthday. The results Beltré turned in during a five-year/$64 million deal with the Seattle Mariners were relatively underwhelming when compared to the monster season he had in his final year with the Los Angeles Dodgers to earn said pact. Beltré rebounded in 2010 after taking a prove-it deal with the Boston Red Sox, enough to convince the Rangers to ink him to a lucrative five-year deal. Though Beltré didn't join the Rangers until his age-32 season, he'll almost certainly be rememberws for what ended up being eight seasons in Texas. During that time, Beltré made three All-Star appearances, won three Gold Glove Awards and helped the Rangers to make their first two World Series appearances.

Roger Clemens
Roger Clemens signed with the Blue Jays after a successful run in Boston. Photo credit (V.J. Lovero-USA TODAY)

7. Roger Clemens - 4-Year/$40 Million Deal With Toronto Blue Jays Ahead of 1997 Season

After 13 seasons in Boston, Clemens became a free agent, signing a four-year/$40 million deal with the Blue Jays. This is believed to be when Clemens first started using performance-enhancing drugs, and the results back up that possibility. After being worth 9.2 fWAR - a solid, but not earth-shattering amount - in his final two seasons with the Red Sox, Clemens was worth 18.9 fWAR between 1997 and 1998, his first two seasons in Toronto. Clemens won the American League Cy Young Award in each of what turned out to be his only two seasons with the Blue Jays, before being traded to the New York Yankees for a package headlined by David Wells.

Alex Rodriguez
Alex Rodriguez joined the Rangers ahead of the 2001 season. Photo credit (Scott Halleran /Allsport)

6. Alex Rodriguez - 10-Year/$252 Million Deal With Texas Rangers Ahead of 2001 Season

The inclusion of Rodriguez's deal on this list may surprise some because the Rangers finished in last place in each of his three seasons with the team. That said, over that same period, Rodriguez slashed .305/.395/.615 with 156 home runs, 395 RBIs and a 27.0 fWAR. Now, we know at least in part what contributed to that production, but Rodriguez was excellent in his three seasons with the Rangers, and returned Alfonso Soriano as part of a trade return from the New York Yankees ahead of the 2004 season.

Manny Ramirez
Manny Ramirez signed with the Red Sox after making his name in Cleveland. Photo credit (M. David Leeds/Getty Images)

5. Manny Ramirez - 8-Year/$160 Million Deal With Boston Red Sox Ahead of 2001 Season

During his final two seasons in Cleveland, Ramirez homered 127 times and drove in 432 runs. That earned him an eight-year/$160 million with the Red Sox, a deal that would ultimately help Boston win their first two World Series titles since 1918. The Red Sox actually tried to trade Ramirez to the Texas Rangers as part of a deal for Alex Rodriguez in December of 2003, less than a year before he'd win World Series MVP.

Greg Maddux
Greg Maddux signed with the Braves after beginning his career with the Cubs. Photo credit (Al Bello/Getty Images)

4. Greg Maddux - 5-Year/$28 Million Deal With Atlanta Braves Ahead of 1993 Season

The Braves won the National League pennant in 1992, already with a tremendous rotation headlined by John Smoltz, Tom Glavine and Steve Avery. But signing Maddux to a five-year deal ahead of the 1993 season took perhaps the best rotation in the game to being one of the greatest in baseball history. Maddux became the ace of a staff that already included two future Hall of Famers, posting a 2.13 ERA and 38.7 fWAR during the five-year deal, both of which were the top marks from starting pitchers over that period. Maddux won the National League Cy Young Award in each of his first three seasons with the team, and helped Bobby Cox's Braves to win the 1995 World Series.

Max Scherzer
Max Scherzer left the Tigers to sign with the Nationals. Photo credit (Greg Fiume/Getty Images)

3. Max Scherzer - 7-Year/$210,000 Million Deal With Washington Nationals Ahead of 2015 Season

Scherzer emerged from Justin Verlander's shadow in Detroit in 2013 to win the American League Cy Young Award. So while it seemed rather shocking for him to turn down a six-year/$144 million extension with the Tigers before the 2014 season, he did so with the belief that he could get a larger deal on the free-agent market. Scherzer bet on himself, and was rewarded after his final season in Detroit with a seven-year/$210 million deal in Washington, a pact that includes deferrals set to pay him $15 million a year from 2022-2028. Scherzer has more than held up his end of the bargain, as he remains among the sport's top starters in the final season of the deal. At the time of publication, Scherzer has won two National League Cy Young Awards and helped the Nationals to win their first World Series title in 2019. Since the beginning of the deal, Scherzer leads all starting pitchers in fWAR.

Randy Johnson
Randy Johnson signed with the Diamondbacks after a stint with the Astros. Photo credit (Todd Warshaw /Allsport)

2. Randy Johnson - 4-Year/$52.4 Million Deal With Arizona Diamondbacks Ahead of 1999 Season

Set to become a free agent after the 1998 season, the Seattle Mariners traded Randy Johnson to the Houston Astros ahead of that year's trade deadline, and he went on an incredible tear. In 11 starts in Houston, Johnson went 10-1 with a 1.28 ERA, earning him a lucrative four-year deal with the Diamondbacks when he reached free agency. Johnson would win the National League Cy Young Award in every single season of the contract, going 81-27 with a 2.48 ERA, 2.53 FIP, 1.044 WHIP and a staggering 37.6 fWAR. Along with Curt Schilling, Johnson helped the Diamondbacks, who broke into the league in 1998, to win the 2001 World Series. Johnson and the Diamondbacks reached a new two-year/$33 million deal after his initial deal expired.

Barry Bonds
Barry Bonds signed with the Giants ahead of the 1993 season. Photo credit (Otto Greule Jr/Allsport/Getty Images)

1. Barry Bonds – 6-Year/$43.75 Million Deal With San Francisco Giants Ahead of 1993 Season

Bonds became a free agent after the 1992 season, a campaign in which he won his second National League MVP Award in three seasons. Bonds, a graduate of Junipero Serra High School in San Mateo, jumped at a chance to sign with what was essentially his hometown team. With his dad, Bobby, serving as the team's hitting and first base coach, Barry won a third MVP award in his first season with the Giants. Over the lifetime of his first contract with the Giants, Bonds was an All-Star every season, slashing .307/.445/.617 with 235 home runs, 660 RBIs, 746 walks and a 1.062 OPS. Bonds would ultimately spend the final 15 seasons of his career with the Giants.

More MLB History Content

- Historical Trade Rumors: Mariano Rivera Was Nearly A Tiger?
- Ranking The 10 Greatest Left-Handed Hitters In MLB History
- Ranking The 10 Greatest Right-Handed Hitters In MLB History
- How Randy Johnson Nearly Joined Curt Schilling In Philadelphia
- The 9 Worst MLB Contracts Of The 2010s

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