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Five of the best Yankees free agent classes

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The Yankees are famous for signing so many superstars over their history. They’ve also been pretty good at signing a bunch of quality guys together.

MLB: ALDS-Boston Red Sox at New York Yankees
CC Sabathia headlines one of the greatest free agent classes in franchise history.
Brad Penner-USA TODAY Sports

Several years ago, Andrew Mearns put together a list ranking the top ten Yankee free agent signings of all time. It features several of the best Yankees to ever put on the pinstripes, and it’s a great analysis of individuals who decided to come to New York.

This story, however, will be a little different. While most of the great signings the Yankees have made came from swiping individual superstars from teams, recently, their most successful moves have come in bunches. Accordingly, I’ve decided to rank some of the best overall free agent classes the Yankees have had.

The year listed indicates when those players entered the free agent market. For instance, any players the Yankees could sign this offseason would fall under the 2018 banner, even if they sign in early 2019. The years I selected stand out because of the number of players signed, rather than having one exceptional player with nobody else around him — sorry in advance to Reggie Jackson and Hideki Matsui. The criteria is centered on the players’ level of stardom when signing with the team, their immediate success in the season after joining the team, and their longevity with the team afterwards. All of these rankings are subjective of course, so you’re free to disagree with the decisions I’ve made.

2000 – Mike Mussina and Robinson Cano

Now, I’m going to immediately make an exception to my rules with this choice, which is why I have it fifth, but I feel like it’s worthwhile. Robinson Cano obviously did not play for the Yankees until 2005, but they did sign him as an amateur free agent in this offseason, and it’s important to highlight what Robbie contributed to the organization during his time here. Cano was a five-time All-Star with the Yankees, placed in the top five in MVP voting three times, and slashed .309/.355/.504 with 204 home runs and 1649 hits. Cano has been one of the most prolific second basemen in league history, and though his suspension this year for using a masking agent clouded his achievements, he was fantastic while in pinstripes.

Mike Mussina was the immediate prize of this free agent class, and his status as a potential Hall of Famer is well deserved. The Moose jumped ship from Baltimore after 10 seasons with the Orioles, and became a mainstay for the Yankees until his retirement following the 2008 season. Mussina went 123-72 over eight years with the Bombers, recording a 3.88 ERA and striking out 1278 batters, which ranks seventh all-time in the franchise’s history. Mussina also stayed consistent in the postseason, holding a career 3.42 ERA and pitching in big moments like Games One and Five of the 2001 World Series, and Game Seven of the 2003 ALCS.

1992 – Wade Boggs and Jimmy Key

The 1992 offseason was a key turning point in Yankees history. It began the transition from the lowest point of the franchise back towards being playoff contenders, though they wouldn’t return to October baseball for a few more years. Two of the signees that led that change were Wade Boggs and Jimmy Keys.

Despite making the last eight All-Star teams, the Red Sox felt that Wade Boggs was on his way down after 1992. The future Hall of Famer hit a career low .259 that season, but picked it back up when he changed sides in the rivalry. In five years with the Yankees, Boggs slashed .313/.396/.407 with 24 home runs, and captured that elusive World Series title in 1996.

Key joined the Yankees and injected life into the starting rotation. He shined in his first two years in New York, earning All-Star selections both years and leading the league in wins with 17 in a strike-shortened 1994. While 1995 was a lost season for Key, who only pitched 30 innings due to a torn rotator cuff in his left shoulder, he returned in 1996 to contribute to the beginning of the dynasty.

2011 – Hiroki Kuroda, Raul Ibanez, and Andy Pettitte

This is a free agent class that gets in not for longevity or flashy signings, but for immediate success. The 2012 squad was the last good Yankees team until the current iteration of the franchise began to form in late 2016. It featured the tail-end of the Core Four, combined with the prime years of the players that won the 2009 World Series, and threw in neat additions like Ichiro Suzuki becoming a Yankee. Some of the year’s biggest contributors however, were signed just that offseason.

Hiroki Kuroda was an under-the-radar signing from the Yankees in the offseason, coming off of four decent years pitching for the Dodgers. Kuroda responded by giving the Yankees the best year of his career, pitching to a 16-11 record with a 3.32 ERA over 219.2 innings. He was the best pitcher the Yankees fielded in the postseason that year, tossing 8.1 innings of two-run ball against Baltimore in the ALDS, and 7.2 inning of three-run ball against the Tigers in the ALCS.

Ibanez had a decent one-year stopover in New York that was accentuated by becoming a postseason hero. In the regular season, Ibanez slashed .240/.308/.453 over 130 games, but made a run late into the year that saw the team bench Alex Rodriguez in favor of him. Ibanez repaid them with a magical performance in Game Two of the ALDS against Baltimore, coming off the bench to swat the game-tying home run in the ninth inning and the game-winning home run in the twelfth.

Pettitte’s contribution to 2012 was limited, but it was a shock that he was on the team at all. Pettitte retired following the 2010 season, but got the itch and signed with the team late into spring training. Pettitte spent most of the season getting back into game shape, eventually pitching in 12 games for the Yankees that year. Surprisingly he still had it, even at 40 years old, pitching to a 2.78 ERA. Pettitte is obviously remembered more for what he did earlier in his Yankees career, but his impact on the 2012 season, when we never expected to see him on the mound again, can’t go ignored.

Also, a fun fact that could bump this up the list in the future: the Yankees signed Luis Severino as an amateur free agent in the 2011 offseason.

1995 – David Cone, Mariano Duncan, and Dwight Gooden

Where 1992 built the foundation for the dynasty, 1995 completed the construction. The Yankees had finally returned to the postseason, had a host of young talent ready to take over key positions for ’96, and now all that remained was to get a few veterans that could support the cast. David Cone is the headliner of the group, a true ace signing, but Mariano Duncan and Dwight Gooden were quality pieces who contributed as well.

Cone was on the team already at the end of ’95 via a trade with the Blue Jays, but still had to negotiate a signing with him before the ’96 season. The three-year, $17 million contract they gave Cone was well worth it, because he shined in the Bronx. Over six seasons with the Yankees, Cone pitched to a 64-40 record and a 3.91 ERA. He pitched a perfect game in 1999, made two All-Star teams and won four titles during his stay.

Duncan entered 1996 after a career built in the National League with the Dodgers, Reds, and Phillies. He had earned an All-Star selection once, but had played in less than 200 games over the previous two seasons. He found his stride again in New York, batting .340 in 109 games. His OBP was only .352, so he was purely going up to the plate looking to swing, but for that season it was successful. Duncan would be traded midseason in 1997, but his hot year in ’96 more than earned his World Series ring.

Gooden was a lost star prior to joining the Yankees in 1995. He was a superstar pitcher with the Mets early in his career, but addiction sent his life into a tailspin. Undeterred, George Steinbrenner saw hope for Gooden, and petitioned for him to sign with the team. Gooden struggled overall in pinstripes, going 11-7 with a 5.01 ERA in 29 starts that year, but nonetheless did his part in bringing a World Series to New York. And not for the New York team that people thought he would’ve, so that’s a bonus.

2008 – CC Sabathia, Mark Teixeira, and AJ Burnett

It comes as no surprise that this ranks as the top free agent class in team history. Coming off of the first year without playoff games in the Bronx since 1994, and with the opening of a brand new Yankee Stadium, Steinbrenner opened up the coffers to bring in every piece he needed to bring home another World Series title.

Sabathia not only is one of the best free agent signings in the team’s history overall, but he came at exactly the right moment for the Yankees. The left-hander was handed the reins from a retired Mussina and took over the role as staff ace. Already on track to potentially be a Hall of Famer, Sabathia further solidified his case, pitching to a 129-80 record with a 3.74 ERA while in pinstripes. His 1593 strikeouts ranks fourth all-time for the franchise, and though he faded in reliability from 2013-2015, CC reinvented himself as a deceptive pitcher rather than relying on the dominating fastball that defined most of his career.

Teixeira was the biggest bat available in the 2008 free agent class, and he fit a perfect need for the Yankees with Jason Giambi’s contract expiring. Tex struggled with injuries throughout most of the second half of his Yankees tenure, but his immediate impact on the team was impressive. He led the league in home runs and RBI in 2009 with 39 and 122, respectively, then led the league in runs with 113 the next year. He even posted another 39 home run season in 2011. Overall, Teixeria slashed .248/343/.479 in eight years in the Bronx, while bashing 206 homers, and was a force in the middle of the lineup for the 2009 World Series champions.

Burnett had a frustrating run with the Yankees, but he undeniably came up big when it mattered most. Burnett was signed partially because he was known as a Yankee-killer with the Blue Jays, so taking him away from the division would be a net positive. Unfortunately, he managed to kill the Yankees from within as well, going 34-35 with a 4.79 ERA in three seasons with the team. His moment of redemption however, came in Game Two of the 2009 World Series, where Burnett tossed seven innings of dominant ball, tying the Series at one game apiece. Everything after that victory for Burnett can be forgotten, though.

Do you have one of these free agent classes ahead of another one? Is your top five entirely different? Let us know in the comments section.