Top 10 MLB Free Agent Contracts of All Time

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MLB Free Agency is one of the biggest crapshoots in all of sports. Given that more and more players are signing pre-arbitration deals that lock them up into their late twenties, most players reach free agency in their early thirties. This means teams have historically had to pay players based on prior production rather than pay for what they’ll do moving forward.

As a result, there have been many albatross contracts in the free agency era, which began in 1976. While there have been many bad contracts handed out to free agents, there have also been numerous contracts that have helped turn franchises around. Humans by nature can be pessimistic so we tend to gloss over many positive events, which means we’ve probably ignored the many great deals that have been signed.

Singling out the best bang-for-buck deals throughout free agency history is fine and dandy, but it doesn’t quite capture the full significance of free agency. Many teams utilize free agency to sign players who can put their team over the hump or represent a building block for future years. The purpose of this exercise is to single out the players who earned their deals and also helped transform the organization’s outlook.

To clarify, this is only targeting free agent deals. Pre-arbitration extensions or extending a currently rostered player did not fit the criteria. Without further ado, here are the 10 best free agent contracts in MLB history.

1. Randy Johnson: Five years, $68 million (Arizona Diamondbacks, 1999-2003)

Arizona was awarded an expansion team following the 1997 season and they were quickly thrown into competitiveness. Johnson was one of the main reasons for their success, winning the Cy Young Award in each of his first four years. During this contract, Johnson put up video game-like numbers: 2.65 ERA, 40 fWAR, 33.5 K%.

Johnson was at his best during the Diamondbacks title season in 2001, when he tossed 17.1 innings in the Fall Classic, allowing just two runs and striking out 19 hitters. Johnson famously won Game 6 of that 2001 World Series and came back out the next night, tossing 1.1 innings en route to another win and helping Arizona win their first World Series title.

It’s hard to envision any player replicating Randy Johnson’s resume, from a free agent standpoint. Four Cy Young Awards and one World Series title in a span of five years is on the list of most impressive feats in baseball history.

2. Barry Bonds: Six years, $43 million (San Francisco Giants, 1993-1998)

The Giants handed Bonds the biggest contract in MLB history at the time, and Bonds was worth every penny. The steroid use will always taint his legacy, but Bonds’ addition forever changed the Giants franchise.

During his first six years with the team, he put up numbers matched by few in the history of baseball. During that timeframe, Bonds hit .307/.445/.617 and averaged 39 home runs and 32 stolen bases a year. His 50.8 fWAR was easily the highest total in that six-year span.

The Giants managed to only make the playoffs once during this time, which speaks more volumes about the club’s roster building than it does about Bonds himself. Essentially a one-man wrecking crew, Bonds did everything in his power to get the team to the playoffs, without any success. Bonds would eventually sign another contract to keep him a Giant for life, becoming the all-time home run king in 2007.

3. Greg Maddux: Five years, $28 million (Atlanta Braves, 1993-1997)

The 1990’s Braves rotation was one the most impressive units ever assembled, consisting of Tom Glavine, John Smoltz, Steve Avery, and Maddux, who was the ace of the group. In Maddux’s first five years, he was easily the best pitcher in baseball, leading qualified starters in fWAR (38.7) and ERA (2.13). He took home Cy Young Award honors in his first three years in Atlanta, which is about as good of an introduction you can have for a new team.

Much like the rest of his career, Maddux excelled during this time by throwing an absurd amount of strikes, walking just 3.4 percent of hitters he faced in this time. Other than the strike-shortened 1994 season, the Braves made the playoffs every year in this time. Their World Series title in 1995 was helped by Maddux’s 2.25 ERA in 16 innings.

4. Alex Rodriguez: Seven years, $145.25 million (Texas Rangers 2001-2003, New York Yankees, 2004-2007)

The Rangers had the right idea signing Rodriguez, but he was a wasted star on a poor roster, which resulted in him being traded to the Yankees after the 2003 season. Rodriguez would eventually opt out of his 10-year, $252 million deal, meaning his original deal ended up being ridiculously team-friendly. The numbers he posted were flat-out stupid in this timeframe.

Rodriguez was baseball’s best player during this time, winning three MVPs and making the All-Star team each year. Rodriguez’s season average in this seven-year span: .304/.400/.591, 47 home runs, and 8.0 fWAR. A-Rod’s offense was 55 percent better than the league average hitter while playing Gold Glove defense at a premier defensive position and providing positive base running totals.

Rodriguez was not without his trouble during his career, namely his involvement in the steroid mess baseball endured, but his on-field production was matched by few others in the history of baseball. He was at his best during this time and was being paid well under his market value to do so.

5. Adrian Beltre: Six years, $96 million (Texas Rangers, 2011-2016)

Beltre has had one of the most productive second halves of a career that we’ve seen from any player. Any skepticism when the Rangers handed Beltre this deal was erased after the future Cooperstown inductee hit .308/.358/.516 during the duration of this deal. His 33.6 fWAR was fourth best mark among position players during this time, while being paid way under market value.

The Rangers made it to the World Series in 2011 and made the postseason three other times during the duration of this deal, with Beltre at the center of all of it. The Rangers couldn’t get over the hump and win their first title, but Beltre did all he could to make that happen. During his Rangers tenure, Beltre notched his 400th home run and 3,000th hit, which all but guaranteed his spot in the Hall of Fame.

6. Manny Ramirez: Eight years, $160 million(Boston Red Sox 2001-2008, Los Angeles Dodgers 2008-2009)

Ramirez was an extremely poor defender, but boy could he hit. During this eight-year span, Ramirez was the third best hitter in baseball, behind two other players on this list (Bonds and Rodriguez). His season averages during this time: .313/.415/.590, 156 wRC+, 4.39 fWAR.

Much like Bonds and Rodriguez, Ramirez found himself caught in the steroid scandal around the game and that has cast a cloud over his legacy and possible induction into Cooperstown. With that said, it’s impossible to argue against the sheer productivity he provided during this time.

Ramirez formed a formidable 1-2 punch with David Ortiz in Boston, helping lead the Red Sox to two World Series championships, eventually finishing the deal with the Dodgers after being traded at the 2008 trade deadline. In his first stint in Los Angeles, Ramirez hit a ridiculous .396/.489/.743 in 53 games and prompted “MannyWood” to begin at the Chavez Ravine.

7. Roger Clemens: Four years, $40 million (Toronto Blue Jays 1997-1998, New York Yankees 1999-2000)

Clemens churned out one of the best two-year stretches ever in his time in Toronto. From 1997-1998, he tossed 498.2 innings with a 2.33 ERA, 20.3 K-BB%, and 18.9 fWAR. Given that this was in the height of the steroid era (although Clemens himself used steroids), these numbers look downright silly.

Infamously, Clemens demanded a trade following the 1998 season and was traded to the New York Yankees, where he fell off quite a bit but still provided quality innings. He ranked 26th in fWAR among starting pitchers during his time with the Yankees but was a rotation cog that was a part of two World Series winning teams.

Overall, Clemens won two Cy Young awards and two World Series titles in this four-year span. Across 890.2 innings, Clemens had the 10th best ERA (3.12) and fifth best fWAR (25.7). Love him or hate him, Clemens put together a historically great four-year stretch.

8. Vladimir Guerrero: Five years, $70 million (Anaheim Angels, 2004-2008)

After eight incredible seasons in Montreal (.323/.390/.588, 33.8 fWAR), Guerrero hit the open market following the 2003 season and had a limited market due to an injury-riddled season. This didn’t bother the Angels, who handed him a five-year-deal and saw him become the cog of an offensive unit that propelled the club to four division titles in Guerrero’s tenure.

In his first year, Guerrero took home MVP honors, hitting .337/.391/.598 and slugging 39 home runs. In this period, Vlad had the 9th best wRC+ (142) and ranked 24th in fWAR (19.7), while being paid way under market value. Other teams clearly missed out on signing Guerrero, who became one of the biggest fan favorites in Angels franchise history.

With his likely Cooperstown induction coming soon, it’ll be fascinating to see if he dons an Expos or Angels cap.

9. Kevin Brown: Three years, $12.6 million (Florida Marlins 1996-1997, San Diego Padres 1998)

This is the shortest contract listed here but it’s impossible to ignore how good Brown was in this time. During this three-year stretch, Brown was certifiably dominant, ranking third in fWAR (22.8) behind Clemens and Maddux, while boasting the lowest ERA (2.33).

It’s easy to forget about Brown given he pitched during the same time as Clemens, Maddux, Pedro Martinez, Johnson, and Curt Schilling. The resume is there, though, backed up by his league-leading 1.89 ERA in 1996 and him leading staffs for two separate World Series teams (1997 Marlins and 1998 Padres).

Brown bounced around from team to team throughout his career, including during this timeframe, but he was a world-class pitcher. Why he didn’t receive more love for the Hall of Fame still remains a mystery today.

10. Jon Lester: Six years, $155 million (Chicago Cubs, 2014-present)

Lester is the only player on this list with a contract still in progress, which means there’s a bit more risk with this placement. With that said, a case could be made that Lester has already earned this deal, based on what he’s done in the regular season and postseason for the Cubs.

Since he signed this deal, Lester is eight among starting pitchers in fWAR (17.6), 13th in ERA (3.10), and 7th in innings pitched (808). More importantly, Lester became the veteran leader and key cog in the rotation, which helped lead the Cubs to their first World Series win in over a century.

During the 2016 title run, Lester had a 2.02 ERA in 35.2 postseason innings, winning the NLCS MVP in the process. Flags fly forever, and Lester’s addition to the Cubs has been invaluable to their organization. With a few more years left on his deal, Lester has a chance to continue to add to his legacy.

Other notable contracts:

Ichiro Suzuki: Three years, $14 million plus $13 million posting fee (Seattle Mariners, 2001-2003)

Nolan Ryan: Four years, $4.5 million (Houston Astros, 1980-1983)

Ivan Rodriguez: Five years, $53 million (Detroit Tigers, 2004-2008)

Kirk Gibson: Three years, $4.5 million (Los Angeles Dodgers, 1988-1990)

Russell Martin: Two years, $17 million (Pittsburgh Pirates, 2013-2014)

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