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The Six Best Free Agent Signings in MLB History

| December 26, 2021 8:15 am PDT

MLB free agency gives teams a chance to land an impact player. Without a salary cap, bigger market teams can shoot for the stars with their signings.

These free agents proved that no amount of money was enough to justify their success. They exceeded their value and then some. All of them won either an MVP, Cy Young, and/or World Series.

Who are the greatest MLB free-agent signings? Let’s start with number six.

6. Toronto Blue Jays Sign Roger Clemens (1997)

Following 13 seasons with the Boston Red Sox, Roger Clemens signed a four-year, $40 million contract with the Toronto Blue Jays.

In his time with Boston, he won the AL Cy Young award three times, and AL MVP once. He was one of the top pitchers, but his ERA slipped a bit in 1995 and 1996. At 34 years old, Red Sox GM Dan Duquette believed Clemens was in the “twilight” of his career.

Clemens went on to show that wasn’t the case. Check out what he did in his first season with Toronto.

Roger Clemens’ 1997 Stats
  • 21-7
  • 2.05 ERA
  • 1.03 WHIP
  • 292 strikeouts
  • 9 complete games
  • 3 shutouts

All of those stats led the AL. Needless to say, Clemens went on to win his fourth AL Cy Young award.

Maybe the best part about that season was his return to Boston. Clemens pitched eight innings, allowing one run and striking out a season-high 16 batters.

In 1998, Clemens returned with another fantastic season.

He posted a 20-6 record with a 2.65 ERA, 1.10 WHIP, and 271 strikeouts. He won the pitching triple crown for the second straight season.

Clemens also won back-to-back Cy Young’s for the second time in his career.

The only issue with Clemens tenure in Toronto was their inability to make the postseason. They failed to win 90 games in either season. That prompted Clemens to request a trade.

Toronto did grant his request, sending him to the New York Yankees. Clemens went on to win the World Series in 1999 and 2000.

For his two seasons in Toronto, the signing looks great. It doesn’t receive a higher placement because he didn’t stick around for the duration. Not to mention, he wasn’t enough to push the Blue Jays into the postseason.

5. Boston Red Sox Sign Manny Ramirez (2000)

A few years after letting Roger Clemens walk, the Boston Red Sox found themselves on the plus side of a free agent signing.

Manny Ramirez was coming off three consecutive all-star game appearances in 2000. He also finished sixth or better in AL MVP voting.

When the Cleveland Indians didn’t meet Ramirez’s asking price, he signed an eight-year, $160 million deal with the Red Sox. The move jump started Boston’s run to their first World Series title in over 80 years.

Ramirez hit over .305 and 30 home runs in each of his first three seasons. In 2002, he led the AL with a .349 batting average and .450 on-base percentage.

In 2004, Ramirez had the best year of his career. He led the AL with 43 home runs and a .613 slugging percentage. What makes it stand out is Ramirez led the Red Sox to their first World Series title in 86 years.

He went on to win World Series MVP with these numbers.

Manny Ramirez’s MVP Numbers
  • 7-17 (.412 batting average)
  • 1 home run
  • 4 RBIs

Ramirez recorded at least one hit in all 14 postseason games.

His success continued in 2005 with 45 home runs and 144 RBIs. He did hit under .300 for the first time in his Boston tenure.

Over the next two years, his numbers dropped slightly. Boston traded him halfway through the 2008 season. This trade was one of the craziest involving a star player.

In his seven and a half seasons with Boston, Ramirez hit .312 with 274 home runs and 868 RBIs. He made the all-star game every season, and was a Silver Slugger from 2001-2007.

Finally, Ramirez finished top 10 in AL MVP voting in his first five seasons with the team. Without him, it’s fair to wonder if Boston ends their World Series drought.

4. San Francisco Giants Sign Barry Bonds (1992)

Some of the younger fans may not know this, but Barry Bonds didn’t spend his whole career with the San Francisco Giants.

Bonds spent the first seven seasons of his career with the Pittsburgh Pirates. He won NL MVP in two of his final three seasons with the team.

Following the 1992 season, Bonds signed a six-year, $43 million contract with the Giants. At the time, it was the largest contract in MLB history.

In his first season, Bonds won his second consecutive NL MVP. Check out his numbers.

Barry Bonds’ NL MVP Stats
  • .336 batting average
  • .458 on-base percentage
  • .677 slugging percentage
  • 46 home runs
  • 123 RBIs
  • 126 walks

With the exception of batting average and walks, Bonds led the NL in all of those stats.

The 1994 and 1995 season both involved less games due to the MLB strike. Bonds led the NL in walks in both seasons, while slugging over 30 home runs.

Bonds finished fifth in NL MVP voting in each of the following two seasons. He hit 42 and 40 home runs, respectively. Bonds also stole 40 bases in 1996.

In his final season under the deal, he hit .303 with 37 home runs and 122 RBIs. He finished eighth in NL MVP voting.

Throughout his first six seasons with San Francisco, he hit .307 with 235 home runs, 660 RBIs, and 194 steals.

Perhaps an all-time show of respect is Bonds led the NL in intentional walks every season of this contract. That includes 1998 when the Arizona Diamondbacks walked Bonds with the bases loaded.

Of course, Bonds went on to spend nine more seasons with San Francisco. He won four consecutive NL MVPs and broke the record for most career home runs.

That run started with a six-year deal in 1992.

3. Washington Nationals Sign Max Scherzer (2015)

Early in the 2010s, Justin Verlander was the ace for the Detroit Tigers. Max Scherzer was their number two guy. Well, that was until Scherzer won the AL Cy Young award in 2013.

With free agency approaching, the Tiger offered Scherzer a six-year, $144 million deal. Scherzer decided to bet on himself and play out the 2014 season.

He had another great season, prompting the Washington Nationals to sign him to a seven-year, $210 million contract.

In his first season with the Nationals, he had a 2.79 ERA, 0.92 WHIP, and 276 strikeouts. He also led the MLB with four complete games and three shutouts.

Two of those came in no-hitters. The second of those came after striking out 17 batters.

Scherzer went on to win the NL Cy Young in the following two seasons. Check out his numbers.

2016 2017
Record 20-7 16-6
ERA 2.96 2.51
WHIP 0.97 0.90
Strikeouts 284 268

Early in the 2016 season, Scherzer became the fourth pitcher in MLB history to strike out 20 batters in a game. That remains one of the hardest MLB records to break.

For the third consecutive season, Scherzer led the NL in strikeouts and WHIP. His 2.53 ERA wasn’t enough to earn him a third straight Cy Young award.

In 2019, Scherzer had another great season. However, the best part of his year came after the regular season.

Scherzer won the World Series for the first time in his career. He started in Game 1 and 7 of the World Series.

He had a down 2020 season and found himself on the move halfway through the 2021 season.

Across those six and a half seasons with Washington, Scherzer went 92-47 with a 2.80 ERA, 0.96 WHIP, and 1,610 strikeouts. He also won a pair of Cy Young awards and made the all-star game six times.

Scherzer bet on himself and won.

2. Atlanta Braves Sign Greg Maddux (1992)

Greg Maddux was one of the top pitchers in the game when he became a free agent. Despite winning the NL Cy Young award in 1992, the Chicago Cubs opted not to re-sign him.

The Atlanta Braves jumped in, giving him a five-year, $28 million deal. Atlanta already had a great rotation, but Maddux proved to be their ace.

Maddux won the NL Cy Young award in his first three seasons with the Braves. His numbers will tell you why.

1993 1994 1995
Record 20-10 16-6 19-2
ERA 2.36 1.56 1.63
WHIP 1.05 0.90 0.81
Strikeouts 197 156 181

Interesting note, he didn’t make the all-star game in 1993.

In 1995, Maddux won the World Series. He had a masterful performance in Game 1, going the distance with two hits and four runs.

While it wasn’t the Cy Young, Maddux had another great season in 1996. He had a 2.72 ERA and 1.03 WHIP. The Braves returned to the World Series for the second straight season.

Maddux shut out the New York Yankees for eight innings in the Braves Game 2 victory. Atlanta eventually lost the series.

The 1997 season marked the final year of his current deal. Maddux finished second in Cy Young voting with a 2.20 ERA and 0.95 WHIP. He did sign a new deal during the season.

Across those five seasons, Maddux had a 2.13 ERA and 0.96 WHIP. He won three straight NL Cy Young awards and made the all-star team four times. Maddux also won the Gold Glove award every season.

His Braves tenure spanned another six seasons, including a pair of top-three finishes in Cy Young voting.

In the mid-1990s, Atlanta had one of the greatest rotations in MLB history. Maddux was the leader of that rotation.

1. Arizona Diamondbacks Sign Randy Johnson (1999)

Randy Johnson didn’t look like an ace at the start of his career. He continued to improve and won his first Cy Young at 31 years old.

Johnson spent the second half of the 1998 season with the Houston Astros. After recording a 1.28 ERA in 11 starts, he signed a four-year, $52 million deal with the Arizona Diamondbacks. It was a bit risky considering Johnson would turn 36 in 1999.

He proved the risk was worth the reward.

In his first season, he helped the Diamondbacks win 100 games and make the playoffs. Johnson won NL Cy Young with a 2.48 ERA, 1.02 WHIP, and 364 strikeouts. He also led the MLB with 12 complete games.

While not as impressive as 1999, Johnson went on to win his second consecutive NL Cy Young. This time, he did it with a 2.64 ERA, 1.12 WHIP, and 347 strikeouts.

The following season, Johnson’s success extended beyond the regular season. He helped lead the Diamondbacks to the World Series.

Johnson pitched a complete-game shutout with 11 strikeouts in Game 2. He picked up two more wins in the series to earn co-World Series MVP with Curt Schilling.

Coming into the season, Johnson had won three straight Cy Young’s. What did he do in 2001? He won another one.

So in four years, he had four NL Cy Young awards, four all-star game appearances, a World Series co-MVP, pitching triple crown (2002), and four-time strikeout leader.

Don’t forget, this all came from age 35-38. It doesn’t get much better than that.

Johnson pitched two more seasons in Arizona, finishing second in Cy Young voting in 2004. He also pitched a perfect game that season.

At the end of the day, he proved to be everything Arizona hoped for.

Other Great MLB Free Agent Signings

  • Texas Rangers Sign Adrian Beltre (2011)
  • New York Mets Sign Carlos Beltran (2005)

Adrian Beltre was a 13-year veteran when he signed with the Texas Rangers. After making the all-star game once in those 13 seasons, he made it four of his six seasons with the Rangers.

He hit .308 with 167 home runs and 563 RBIs.

Following a big 2004 postseason, Carlos Beltran signed a seven-year deal with the New York Mets. Beltran made the all-star game five times. He also hit 149 home runs.

These players showed just how big of an impact one free agent signing can have.

The ultimate goal for a baseball player is to win the World Series. Catch up on past World Series in the articles below.

Nicholas Sterling

Nicholas has been a Sports Writer with GamblingSites.com since May 2021. He has a rich sports background, writing about NASCAR, NFL, NBA, MLB, NHL, Golf, etc. Nick is always ready for a new challenge.

He enjoys rooting on D.C. sports teams, including the Commanders, Wizards, and Capitals.

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