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A smiling Yankee President Gabe Paul, right, announces Tuesday, Dec. 31, 1974 in New York, that the American League team has signed ace pitcher Jim ‘Catfish’ Hunter to a contract. Exact figures were not announced at the news conference at New York, but the Associated Press learned that the contract would total about $3.75 million over its five year life time, giving Hunter, left, something to smile about. (AP Photo/Ray Stubblebine

Yankees most important free agent signings

The Yankees haven’t made any headline-grabbing signings in this year’s free-agent market, which is unusual for them compared to past offseasons. The team has signed a number of free agents over the years, but as of this writing, Matt Holliday has been their sole “prize” this winter. And, he’s working on a one-year contract. As with any team, the results of the Yankees signings over the years have been a mix of highs and lows. Signing a free agent isn’t much different than gambling on the stock market. You hope you got the “stock” (player) at the right time and “it” (he) produces for as long as you have “it” (him) in your “portfolio” (on your payroll).

Without going into depth here, every Major Leaguer that signs a free agent contract owes a debt of gratitude to Curt Flood. It cost him his baseball career, but his fighting baseball’s reserve clause opened the door for free agency. So while you patiently wait for the 2018 offseason, when Manny Machado, Bryce Harper, Clayton Kershaw and Brian Dozier possibly become free agents, here are arguably the three most important Yankees’ free agents signings. (Not including re-signing of their own free agents.)

Reeling in a Catfish

Jim Hunter: His real name looks odd in print, but Jim “Catfish” Hunter is in the baseball Hall of Fame. He had an illustrious career with the Oakland A’s and New York Yankees. And, the reason he was a Yankee was that he was baseball’s first free agent, thereby also making him the first major free agent signing by the Yankees.

Catfish’s free agency was not a simple deal. Oakland paid half of the $100K owed Catfish for 1974, but the rest was to be paid out in monthly installments to an insurance annuity. Team owner Charlie Finley was late on the payments.

Then-commissioner, Bowie Kuhn, ordered Finley to pay up. The eccentric A’s owner wanted to give the remaining money in a lump sum, but Catfish refused. Finley countered by refusing to pay the remainder of the contract. The Players Association chief, Marvin Miller, had to get involved. Miller was admittedly nervous that the outcome of arbitration could be free agency.

“One thing worried me,” Miller later reflected. “The remedy was free agency. That was drastic. I thought it might be too drastic for an arbitrator.”

There was also the matter of teams not being used to signing a player who could go wherever he wanted. Everyone recognized that what was to follow would set the tone fo free agency in the future. As for Catfish, he was coming off of a Cy Young Award winning season in which he won 25 games and had a 2.49 ERA. Both figures topped the American League.

It’s unlikely that anyone in baseball anticipated the bump-up in pay that Catfish would receive. On New Year’s Eve, 1974, the Yankees announced that they and Catfish had agreed to a five-year, $3.73MM deal. The new contract also featured a $1MM signing bonus. Overall, it was a 600% increase from his previous annual salary.

Catfish’s impact on and off the field was huge. He was a proven winner, a three-time World Series champion, and a perennial All-Star. He came to New York having averaged 22 wins the prior four years, twice leading the AL in winning %. During his time as a Yankee, Catfish mentored young pitchers like Ron Guidry and was an instant ace on a team that needed one.

He finished second in the Cy Young voting in 1975 after he led the league in wins (25), complete game (30), innings pitched, WHIP (1.009), and H/9 IP (6.8). Despite arm trouble from his many innings thrown in a 15-year career, Catfish was an integral part of getting the Yankees back to winning. One year after his signing, the Yankees reached the World Series for the first time in 12 years. And, in 1977-1978, they won their first titles since capturing the 1961-1962 championships in back-to-back years.

Mr. October

Reggie Jackson: Like Catfish, Jackson was a part of the Oakland A’s dynasty from the early to mid-1970’s. The team captured five straight division titles and three straight AL pennants and World Series championships. Before he came to New York, Jackson already had the take-no-prisoners swing, the swagger, the ego and the tape-measure home runs. But, playing in Oakland is NOT like playing in New York.

One by one, the A’s players were having trouble with Finley. More specifically, the players wanted the money owed to them and more significant pay raises. Jackson hit 47 home runs in 1969, won the 1973 AL MVP when he led the AL in HR, RBI, and runs scored, and was coming off of a 36 HR-118 RBI season when things came to head in early 1976. The A’s shipped Jackson, Ken Holtzman and a minor leaguer to the Baltimore Orioles for Don Baylor, Mike Torrez, and Paul Mitchell.

Jackson had plenty of teams interested in him after he finished fourth in the 1976 AL MVP vote, but not many teams could afford him. The Yankees needed a hitter that would put the fear of God into opposing pitchers. Reginald Martinez Jackson was that man and Yankees owner George Steinbrenner had his sights set squarely on the All-Star outfielder.

On November 30, 1976, the Yankees signed Jackson to a five-year deal that would pay between $2.1MM and $2.4MM. What followed over the next five seasons involved plenty of drama, managers, home runs, wins and chaos. Jackson seemed to be in the middle of most of it, the winning included. But, he provided the dangerous bat the Yankees desperately needed.

That first October in ’77, in the big lights of the big city, he became a New York legend. The Yankees led the Los Angeles Dodgers three games to two in the Fall Classic. Yankee Stadium hosted Game 6 with the Yankees’ Torrez going against the Dodgers’ Burt Hooton. Down 2-0 in the 2nd inning, Jackson drew a lead-off walk and Chris Chambliss followed with a home run. The Yankees trailed 3-2 in the bottom of the 4th inning when Jackson came to bat.

Jackson turned on Hooton’s first pitch and smashed a shot into the upper deck in right field to tie things up once again. One inning later, Jackson came to the plate with a man aboard and the Yankees ahead 4-3. This time Jackson hit a laser beam into the lower deck in right field on reliever Elias Sosa’s first pitch.

The Yankees had increased their lead to 7-3 when Jackson led off the 7th inning against knuckleballer Charlie Hough. Jackson wasn’t patient at the plate in his last at-bat of the night either. He took a mighty swing at the first pitch from Hough. The baseball landed in the black-painted batter’s eye in dead center field, approximately 450 feet away.

The Yankees went on to an 8-4 victory and their first World Series title since 1962. Jackson’s three home runs on three swings in the Fall Classic earned him the nickname “Mr. October”. In actuality, Jackson had homered in four straight official at-bats, since he also homered in his last at-bat in Game 5. And, at least temporarily, Steinbrenner, Jackson, and manager Billy Martin were one big happy family.

Andy 2.0

Andy Pettitte was already a Major League Baseball star when he returned to the Yankees in 2007. Pettitte had established himself as a fan favorite during his first tour in the Bronx (1995-2003). But, many were sad and/or angry when he bolted as a free agent in 2004 and spent three years as a Houston Astro. In December 2006 he decided to don the pinstripes once again and signed a one-year deal worth $16MM.

Pettitte’s return to the Yankees came at the right time. Since their last trip to the World series in 2003, the Yankees had blown a 3-0 lead to Boston in the ALCS and lost twice in the first round of the playoffs. An experienced, winning pitcher who could give the team 200+ innings was a welcome addition.

Though the Yankees lost once again in the first round of the 2007 postseason, the Texas native helped get them there. He threw a team-high 215.1 innings and topped the rotation with 34 starts and 141 strikeouts. His 4.05 ERA and 15 wins were second only to Chien-Ming Wang. Just as importantly, his return led to more time as a Yankee, including another comeback in 2012 after taking the 2011 season off.

Pettitte’s value wasn’t just measured by his success on the mound. He also served as a mentor. He was a good sounding board for veterans like Mike Mussina, who was struggling with injuries and a lack of speed and sharpness in his repertoire of pitches. Having gone through some of the same struggles, Pettitte was able to offer some sage advice.

Pettitte’s 2008 season was uneven as was the team’s year overall. The final year in the old Yankee Stadium ended with no playoffs for the first time in a dozen seasons. That winter, the Yankees added CC Sabathia and A.J. Burnett to the rotation and first baseman Mark Teixeira to the lineup. In late January, Pettitte decided to return and he was back to being his consistent self when the season got underway.

He nailed down 14 wins in 32 starts, as the team returned to the World Series for the first time in six years. The trip to get there saw Pettitte at the forefront. He beat the Twins in the Division Series finale with six-plus shutout innings. In his second start of the ALCS, he topped the Angels to win the pennant.

With the World Series tied at a game apiece, Pettitte regrouped after allowing three early runs and won Game 3. Then, with the Yankees up in the Series three games to two, Pettitte took the mound for the clincher. He wasn’t at his best, but he limited the Phillies to one run over five-plus innings.  The Yankees came out on top 7-3 to raise Pettitte’s 2009 postseason record to 4-0, and in doing so they won their 27th World Series Championship.