Yankees Best Free Agent Signings in History


Yankees Best Free Agent Signings No. 2 –

Adam: Dave Winfield – 10 Years/ $23 Million

In 1980, when Dave Winfield signed his contract with the Yankees it was the richest contract in sports history. Wow, how things change huh? Have you read somewhere that it was a $16 million contract? So did George Steinbrenner and that is where the feud between the two began. Factor in a 1-for-22 World Series in 1981 and the nickname of “Mr. May” was born. Things got so bad that Steinbrenner paid a PI to find dirt on Winfield which led to a ban from baseball for Steinbrenner.

Despite all that, Winfield just produced. While a Yankee he went to eight All-Star games and slashed .290/.356/.495 with an OPS+ of 134. Add in another 205 home runs, over 800 RBI, and a WAR at an insane level of 26.9. While the Yankees did not have success in his tenure, it was not a product of underperformance by Winfield. The only real sad thing is that rift with Steinbrenner is why Winfield went into the Hall of Fame with a Padres hat on his head. All of that places him comfortably at number two on my list of Yankees best free agent signings.

RichMike Mussina – Six Years/ $88.5 Million

Poor Mussina.  He spent his entire career in the AL East facing the Yankees and the Red Sox, and then when he got to the Yankees as a free agent, it was just after the dynasty run of the late 1990s.  The team made the World Series twice with Mussina as a starter (missed the playoffs only once), but lost both times (2001 to the Diamondbacks and 2003 to the Marlins).  However, it was not Mussina’s fault.  He was, in my opinion, the best Yankees starting pitcher during his tenure with the Yankees.  He did whatever was asked of him, including coming out of the bullpen and pitching three flawless innings in the famous Aaron “Bleeping” Boone game against the Boston Red Sox in the 2003 ALCS.  Mussina went out on top winning 20 games in his final season, not only for the Yankees but for MLB – he retired after the 2008 season (and of course the Yankees went out and won the World Series in 2009).  An argument can be made that he is the best free agent signing ever in Yankees history, but the lack of a World Series victory during his tenure tarnishes the argument a little.


Yankees Best Free Agent Signings No. 1 –

Rich: Reggie Jackson – Five Years/ $2.96 Million

Naming Jackson my number 1 was not easy.  He was not with the team very long after signing as a free agent, but man oh man, what an amazing five years it was.  The Yankees won multiple World Series titles during his tenure and of course, you had the amazing run of HRs against the Dodgers in 1977.  Yes, his “straw that stirs the drink” ego didn’t sit well with manager Billy Martin or Captain Thurman Munson, but what really matters is what Reggie did on the field, and that was simply slug and win.  Reggie was brought in to help the Yankees win World Series titles and that is exactly what he did.

Adam: Mike Mussina – Six Years/ $88.5 Million

My gut tells me that there will be a lot of flak for this choice and some will call me a fool or a writer that knows nothing about the Yankees. I would argue, in advance, the opposite. Ironically, in this modern era, Mussina pitched in New York during “the gap.” He joined the team in 2001 (right after the 2000 Subway Series) and pitched in pinstripes until his last season in 2008 (right before the 2009 World Series title). The Yankees missed the playoffs only once during his time.

During his tenure in New York, Mussina has a 3.88 ERA, a 114 ERA+, a FIP of 3.50, and 123 wins. He pitched his whole eight-year contract and set a personal best in wins during his last campaign. It was hard to believe but it was his first 20 win season at 39 years old.

Some of Mussina brightest moments were overshadowed by other iconic Yankee moments. Examples? Sure. Remember “the flip” against Oakland? Well, Mussina pitched seven shutout innings in that “season on the line” game that was overshadowed by the incredible plan by “The Captain.” Another example? Remember the iconic Aaron Boone ALCS do-or-die home run that dubbed him Aaron “bleepin” Boone? Mussina was asked to come in for relief and pitched three incredible relief innings to keep the season alive. True to his personality, he came to work and did his job. He rarely threw a dud and took the ball in many high-stress locations without fail. While it might not be popular, Moose is number one on my list of Yankees best free agent signings of all-time.


Yankees Best Free Agent Signings Final Thoughts

Adam: Sure, there are plenty of guys I could have included but you have to draw the line somewhere. I would not fault anyone for including Goose Gossage , Johnny Damon, or Hideki Matsui but for the five I mentioned are just more impactful. Again, it is literally splitting hairs when trying to rank the top-five Yankees best free agent signings. I feel solid in my final five but the three mentioned above could have easily been number four or five. I considered the total package including the length of service, team success, personality, and performance under pressure as my metrics. I hope you enjoyed.

Rich:  I decided to avoid the international free agent signings of Orlando Hernandez and Hideki Matsui (both of whom could have easily made this list) – to me, the international free agent market is always a wash and the Yankees truly never had competition for the best international players due to money; for every Matsui you have an Igawa, for every Hernadez you have an Irabu.  I wanted to go with free agents that were proven in MLB before they were signed, not just a roll of the dice (even though all free agent signings are rolls of the dice).  As you can see, Adam and I did not agree about the order whatsoever, though we did have four of the same players in our top 5s.  I am sure your top 5 is different as well.


Now you know out Top-5 Yankees best free agent signings in history. Here at NY Yankees Digest we are all for readers commenting but can we make a suggestion? Why don’t you write your own piece? It can be 3000 words or even 300.  Here we encourage different opinions and want to give you a chance to build your brand. Join us and let your voice be heard. Just check out the Write With Us link to get started. Don’t worry its easy and remember you can build your brand by writing with us and not for us. That is a big difference. It is all about you in your words.

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