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Ranking Yankees’ best free-agent signings to date

I thought I had given myself an easy task.

One day, I was talking to Gerrit Cole and it occurred to me that he had to be emerging as one of the best free agent signings in Yankees history. Indeed, I thought I would make a list. How difficult would it be? Reggie here, Goose there, and CC.

But the fact is, the Yankees have signed a lot of free agents over the course of that half-century, and despite what people may think, not all of them were Kei Igawa or Carl Pavano.

Therefore, rules were needed as a way to thin out the herd. Therefore, we decided not to include re-signed free agents such as David Cone, Alex Rodriguez, and Bernie Williams. These players have already played for the Yankees. I wanted the bucket that Cole belonged to, but in a completely new situation.

That simplified the problem, but it didn’t make it easier. Even a top 10 list would leave out some really good Yankees. Also, do you prioritize being worthy of a championship appearance above all else, among other things, or is Dave Winfield’s year-to-date performance higher than, say, putting him on the list over, say, Johnny Damon? It also made me think about whether I should push it further. Who are the key players in the 2009 championship?

Cole has had a great four years with the Yankees, and it’s clear that if he continues to perform well during his contract and can win a title or two, he probably has a chance to rise to the top. Anyway, this is one person’s list. Let’s start the discussion:

1. Reggie Jackson: There are many reasons why he is No. 1. After the Yankees lost to the Reds in the World Series, he signed a five-year, $2.96 million contract as a finishing touch. He became Mr. October. There are two titles. He was a candy bar, a celebrity, the main character in the Yankees’ soap opera of the day.

New York Yankees outfielder Reggie Jackson #44 signs autographs for a fan during a 1980 spring training game in Tampa, Florida. Getty Images

2. Orlando Hernandez: This might be a little high for a lot of people, but if you told me you could pay full price, get a game, and get any Yankees player from the last 30 seasons, I wouldn’t even blink — El. It’s Duque. He posted a 3.96 ERA in six regular seasons with the Yankees. He played in 17 postseason games for the Yankees, posting a 2.65 ERA and helping them win three titles. His seven-inning shutout in Game 4 of the ALCS in Cleveland essentially saved the Yankees’ best season in 1998. His story of his escape from Cuba became the subject of this week’s movie, and the Yankees signed him to a blockbuster four-year, $6.6 million contract. -Game Master.

3.CC Sabathia: He joined the team for a seven-year, $161 million deal, a pitching record at the time, as the ace of a winning team and to unify a clubhouse in disrepair. Check and check his first year.

4. Goose Gossage: Blackmail. Fastball. moustache. Even though the Yankees won the 1977 championship and Sparky Lyle won the AL Cy Young Award, George Steinbrenner still invested $3.6 million over six years in Gossage. His reward was another title in 1978 and six seasons with Gossage, where he posted a 2.10 ERA.

CC Sabathia, who came in third on this list, was photographed pitching in the bottom of the sixth inning against the Seattle Mariners on July 2, 2009 at Yankee Stadium in the Bronx. Getty Images

5. Dave Winfield: “Mr. He won five Gold Gloves, won top-eight MVP awards four times, and posted an OPS of 134 or higher.Always wanted more, but he gave the Yankees a lot.

6. Catfish Hunter: He’s here because he was a pioneer and because he gave his last arm to the Yankees. He was the first big-money free agent, signing a five-year, $3.25 million contract, and in many ways established the way Steinbrenner did big business. In his first season with the Yankees in 1975, Hunter won 23 games and pitched 328 innings. He wasn’t really the same, but he contributed to the 1977-78 championship.

7. Gerrit Cole: Really, I didn’t know where to put him on the list. That he would be given more after the AL Cy Young, and that he’s on the list because he won the Cy Young, but now he’s accomplished more as a Yankee. I’m certainly biased knowing that Mike Mussina, who is there, is not on the list. For Cole to truly make the list, he’ll need a postseason similar to the one he had in 2009 with Sabathia leading the team.

Dave Winfield stands at bat during a major league game at Yankee Stadium in the Bronx, circa 1988. Getty Images

8. Hideki Matsui: It was his second contract with the Yankees, where he won World Series MVP in 2009. But in his first contract, which was for three years and totaled $21 million, Matsui appeared in every game for the Yankees from 2003 to 2005, posting an OPS of over 125. If Duque is my important pitcher, I might put Matsui in his biggest at-bat. He was fearless.

9. David Wells: He holds a unique spot on this list, having been signed as a free agent at two different points: after the 1996 season and after the 2002 campaign. He caused a lot of headaches. But he also pitched a perfect game, was the ace of the 1998 championship, was a key piece in the trade to Toronto for Roger Clemens, and pitched more than 851 sq./₃ innings in four seasons for the disjointed Yankees. He won 68 games.

10. Jimmy Key: There were many ways to get here, all of them legitimate. Damon. Mussina. Mark Teixeira. Masahiro Tanaka. Tommy John. That’s the first DJ LeMahieu deal. But I feel like the key has been forgotten in time. He was a very important transitional player, from the dark days of the early 1990s to the dynasty by the end of the decade. The Yankees literally tried to sign seven other free agent starters after the 1992 season, most notably Cone and Greg Maddux. They settled for four years and $17 million for the keys since no one received the money.

Key brought unwavering character, professionalism, and an expectation to win as the Yankees began a still-winning season in 1993, his first year. They finished 4th in the AL Cy voting that year and took 2nd place the following season. Although he missed most of 1995, he made a major contribution to the 1996 championship, including a decisive victory in Game 6 of the World Series.

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