Yankees Best Free Agent Signings in History


Yankees Best Free Agent Signings No. 4 –

Adam: Orlando Hernandez – Four Years/ $6.6 Million

El Duque was technically an international free agent signed to an MLB contract but for the intent of this piece he was a free agent that signed so I am going to count it since he was in his 30s (?) and it was Cuba (which in itself was complicated) instead of a country like Panama (So no Mo). The Cuban defector was a key member of three straight World Series titles. During his time in pinstripes, El Duque made 136 starts with a 116 ERA+ and a 10.6 WAR.

It was the post-season where he really stepped it up. He made 17 post-season starts during his time with the Bombers and went 9-3. His crowning moment was taking the ball with the Yankees down 2-1 in the ALCS. He responded with seven scoreless innings and launching the team on a winning streak that lasted through the World Series title. It was that original contract that was an insane value. I cannot disagree with Brian Cashman was said, “El Duque would probably be the best because he was so cheap and for four years, he turned out to be so valuable.”  That places him comfortably at number four on my list of Yankees best free agent signings.

Rich: Dave Winfield – 10 Years/ $23 Million

It is hard to believe that Winfield’s contract was once considered the most ever in MLB history (the entire value of the contract is less than what superstars make per year now).  The Yankees never won a World Series with Winfield patrolling right field, though they did make one in 1981 (losing to the Dodgers where Winfield did not produce and earned his “Mr. May” nickname).  During the regular season, Winfield was a perennial MVP candidate and batting behind Don Mattingly gave the Yankees a killer 3-4 in their lineup.  While his time with the Yankees ended badly (due to George Steinbrenner’s actions hiring a private investigator to look into Winfield), Winfield did what he was supposed to for the Yankees in the field and at the plate.  The lack of a World Series victory is why he isn’t higher in my rankings.


Yankees Best Free Agent Signings No. 3 –

Rich: CC Sabathia – Seven Years/ $161 Million

CC Sabathia was signed to do one thing – help the Yankees win a World Series, and they did just that in his first season with the Yankees in 2009 (along with Mark Teixiera, the Yankees went nuts in that offseason with free agents).  While CC’s final years of the contract were “overpaid” in many fans’ opinions, it was the first few years of the deal that we got the value from it.  CC stepped in after Mussina’s retirement and became the Yankees ace and it was almost like the Yankees got a great deal for what CC delivered in those first four years.  To this day, CC remains a member of the Yankees and will probably retire as one.

Adam: Reggie Jackson – Five Years/ $2.96 Million

What a five years. The good, the great, and the ugly. Most people will have Reggie Jackson as the number one or two free agent signing in Yankees history but for me, he slides a bit for the turmoil his over the top personality created in the locker room. He spent a lot of time in 1977 and 1978 feuding with Billy Martin and Captain Thurman Munson.

Now on the field, that is a different thing altogether. In his five years in New York, Jackson slashed .281/.371/.526. He belted 144 home runs and carried a WAR of 17.1. Now we all know what Jackson is remembered for. In the 1977 World Series Game 6, he belted three straight home runs on the way to a Series MVP and to his first of two Yankees World Series titles and the nickname “Mr. October.” The attitude should not matter but when you are down to the wire ranking the Yankees best free agent signings and need something to break the ties you get Jackson at number three on my list of Yankees best free agents.

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