Yankees’ top 10 best free agent signings

10 best Yankees free agents
John Allen
Sunday February 5, 2023

Table of Contents

The Yankees have signed many free agents over the years. While many went on to become blockbuster successes, others proved to be a costly affair for the team that boasts the most number of World Series wins. All of them have made news, either by helping the team reach new heights or by turning headaches for the Bronx faithful.

Here is a list of the Yankees’ top ten free agents signed. Their selection is based on how big they were at the time of their signing and how they performed.

#10. David Cone, 1995

Cone arrived in the Bronx in the middle of 1995 in a trade with the Blue Jays. However, he became a free agent, who the Yankees re-signed him for $19.5 million and three years. He was a key part of the Yankees’ four World Series wins. In 14 postseason games, he went 6-1 with a 3.86 ERA in 12 starts.

Cone was much more than his 64-40 record and 3.91 ERA as a Yankee. He showed leadership after he came back from an aneurysm in 1996. Cone pitched a perfect game on July 18, 1999, against Montreal before the home crowd.

#9. Mike Mussina, 2000

The Yankees signed Mussina to a six-year, $88.5 million deal after the 2000 season. This gave a team that had already won three championships another ace pitcher. With Mussina’s help, the Yankees advanced to two more World Series though they didn’t win another ring. But Mussina remained and pitched his first 20-win season in 2008, which was the last year of his Yankees career.

The Yankees admired the reliability of Mussina. As a Yankee, he went 123-72 with an ERA of 3.88, which helped him build a Hall-of-Fame resume. He pitched in several memorable postseason games, including seven scoreless innings in the famous Flip Play game and three crucial scoreless innings in Game 7 of the 2003 ALCS, which set up Aaron Boone’s moment.

#8. Jason Giambi, 2001

Giambi replaced the popular Tino Martinez, who earlier came to relieve Don Mattingly. He signed a seven-year, $120 million contract after becoming a free agent in 2001 winter. He wore No. 25 because 2 + 5 equals 7, the number of Mickey Mantle, who Giambi’s father considered his favorite player.

During his New York stint, Giambi hit 209 home runs, got on base .404 of the time, and had an OPS of .925 from 2002 to 2008. However, he was linked to the BALCO scandal in early 2004 and reportedly sought a non-specific apology in 2005.

#7. Hideki Matsui, 2002

Even though he signed a smaller deal compared to the first Yankees Japanese contract, fans took a sigh of relief when Matsui signed with the Yankees. New York had previously roped Japanese hurler Hideki Irabu. But Matsui turned out to be a title winner for them.

Matsui was a huge star in Japan because he hit 50 home runs the year before and played in a lot of games in a row. Fondly called Godzilla, he had four seasons with 100 RBIs and was the most valuable player in the 2009 World Series.

#6. Gerrit Cole, 2020

Fans had been complaining for years that the Yankees don’t have an ace pitcher for Game 1 of a playoff series. The Yankees put an end to that complaint by signing Gerrit Cole, a pitcher they had liked since he was in high school. His $324 million deal over nine years is the most money ever given to a pitcher in the Bronx.

Cole notched up a 7-3 record and a 2.84 ERA in 2020. Next season, he struck out 243 and had a 3.23 ERA while his 16 wins more the most in the American League. In 2022, he surpasses Ron Guidry’s 1978 team record and ended with 257 strikeouts, the best in MLB. His ERA was 3.50.

#5. Dave Winfield, 1980

The Yankees are good at giving players the highest-paying contracts, and they did that with Winfield in 1980 when they gave him a 10-year, $23 million deal. At the time, it was the richest in baseball history. In nine years with the Yankees, Winfield hit 205 home runs, had an OPS+ of 134, and was named to eight All-Star teams. Plus, the fight with Mattingly for the AL batting title in 1984 was a memorable event.

During his time with the Yankees, he also had a fight with George Steinbrenner, who called him “Mr. May.”

#4. Alex Rodriguez, 2007

Alex Rodriguez is in a funny pose

When word got out that A-Rod was getting out of the last three years of his contract during Game 4 of the 2007 World Series, it wasn’t very cool. That caused some pinstriped drama and made people wonder if he’d ever come back to the Yankees.

But with help from Goldman Sachs, the Yankees and Rodrguez finally came to an agreement on a 10-year, $275 million contract. At that time, it was the biggest contract in the sport. Though Alex Rodriguez couldn’t have another MVP year, his hitting prowess was an asset for the Yankees and they went on to win the 2009 World Series.

#3. CC Sabathia, 2008

Maybe it’s cheating to put “The Splurge of 2008-09” in just one spot, but it’s hard to fit so many Yankee splashes into a list of 10. So a little bit of lying it is! The Yankees spent a total of $423.5 million that winter to sign CC Sabathia, Mark Teixeira, and AJ Burnett. It paid off right away when they won the World Series in 2009. Also, Sabathia was the Major-League leader with the maximum win for two consecutive years.

#2. Catfish Hunter, 1975

Hunter, who signed a contract worth $3.75 million over five years, is credited with pushing a team that was already good enough to win to reach new heights. This signing was huge in the early days of free agency. Hunter came into the 1975 season with a lot of championship experience, having won the World Series three times in a row for Oakland from 1972 to 1974.

In his first year with the Yankees, he led Major League Baseball with 23 wins, 328 innings, and 30 complete games. The next year, Hunter went 17-15 and led the Yankees to the first of three straight World Series titles, between 1976 and 1978.

#1. Reggie Jackson, 1976

He was a perfect match in a free market. The best player in baseball went to the best owner who wanted stars and played big-time ball for him. After the 1976 season, Reggie Jackson signed a five-year contract worth about $3 million. He then became known as “Mr. October” by hitting three home runs in Game 6 of the 1977 World Series. The Yankees won the Fall Classic again with Jackson the next year, and they went to a third in 1981. During the length of the contract, he was an All-Star five times and hit 144 home runs and drove in 461 runs for the Yankees.

Jackson got a lot of attention both for his batting and fights, and he always did his best on the field. His playoff stats stand at 1.090 OPS and 12 home runs in 34 games.

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