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For the holiday season: The Yankees' Top 10 free agent signings of all-time

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Counting down the best presents under the tree Yankees fans have ever received.

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It's the holiday season, with Hanukkah in full swing, Christmas just around the corner, and the Festivus Airing of Grievances toward malfunctioning technology as pointed as ever. The off-season is a time when many Yankees fans turn to Yankee Stadium in hopes of finding wonderful presents under their metaphorical trees. (Perhaps Monument Park serves as a stand-in, though it would be difficult to actually locate anything hidden under the monolith to Steinbrenner Face's bulging jowels.) Sometimes, the gifts are Masahiro Tanaka-like gems, though other times, we are forced to settle for a factory-used Freddy Garcia that leaks some unsettling substances.

No one should want to think about the negatives this time of year though, so let's count down the Yankees' top ten ever free agent signings in the hope that Hal Claus and his Pop Tart-infused elf assistant Hank can conjure up some surprises on Christmas morning. Get the eggnog flowing, and keep in mind that this list is, of course, subjective, and this just includes new acquisitions, not re-signings.

10. Johnny Damon, 4/$52M, 1/3/2006

Damon has always been kind of annoying off the field for his outspokenness, to put it politely, but there's no denying that he was one of the best outfielders of the past two decades. When he signed a four-year deal with the Yankees and bolted from the Red Sox, it set off the creation of hundreds of "TRADERRRR" posters from Boston fans, incensed that Damon signed in the Bronx after vowing he'd never play there. For Yankees fans though, it was pretty awesome, as GM Brian Cashman had played his cards close to the vest all off-season, famously insisting that he was just fine using role player Bubba Crosby as his center fielder.

Cashman won the waiting game without having to resort to Hungry Hungry Hippos, and the Yankees certainly reaped the benefits. Even though Damon was already 32, he defied his critics who said his speed-based game wouldn't age well. Over his four years in pinstripes, he hit .285/.363/.458 with 125 doubles, 93 stolen bases, and 14.4 WAR. The lefty-swinging Damon also took great advantage of the short porch at both the old and new Yankee Stadium, smacking 77 homers. The Yankees made the playoffs three out of his four seasons, culminating in the 2009 World Series title, a Fall Classic in which Damon hit .364/.440/.445 and brought his baserunning exploits center stage in a pivotal Game 4 rally against the Phillies. Now that's a sound investment.

9. Jimmy Key, 4/$17M, 12/10/1992

The Yankees were terrible on the field and in turmoil in the early '90s, and it was up to GM Gene "Stick" Michael to keep them afloat in relevant in what was becoming a Mets town. Owner George Steinbrenner was suspended from the game, and Michael had near-full control over who we wanted on his team. Spurned by Greg Maddux and David Cone during the 1992-93 off-season, Michael was happy to settle for the lefty Key, a longtime division rival with the Blue Jays. It was a big off-season for Michael, as trade acquisition Paul O'Neill and Key's fellow free agent signing Wade Boggs (a very near-miss for this list) propelled the Yankees to an over-.500 record in '93. They have incredibly not fallen below that mark in 22 seasons now.

Key instantly brought stability to the Yankees rotation, and they had an ace who young manager Buck Showalter knew he could trust. Key was an All-Star in his first two seasons as a Yankee, pitching to a 3.11 ERA (139 ERA+), a 3.60 FIP, and pitching 404 2/3 innings. That total could have been even higher, too, if the players' strike did not cancel the remainder of the '94 season in the middle of August. (Thx, Selig.) Rotator cuff surgery sidelined him for almost all of the Yankees long-awaited playoff run in '95, but he returned to the team under new manager Joe Torre in '96 ready to help lead the rotation again, this time with Cone as well. Key pitched to a reliable 107 ERA+ over 30 starts as the Yankees won both the division title and World Series, with Key pitching 5 1/3 innings of one-run ball against the Braves in the Game 6 clincher, his last start as a Yankee. Plenty had to go right for the Yankees to return to relevancy, and Key was... key to their ascent.

I'll show myself out now.

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8. Orlando Hernandez, 4/$6.6M, 3/23/1998

Including "El Duque" on this list is a bit of a reach since he wasn't signed until late in spring training, but whatever. On a pure value basis, few contracts have been better than the comparatively measly $6.6 million invested in El Duque back in 1998. A Cuban phenom, El Duque escaped the country in an emotionally trying manner, desperate to join his half-brother Livan Hernandez in the major leagues on the heels of Livan's World Series MVP-winning performance in '97 with the upstart Marlins. Minor leaguers could do nothing with the (possibly) 32-year-old rookie's repertoire, and when David Cone had to miss a start due to a bite on the finger from his mother's Jack Russell terrier, he got his shot. He pitched so effectively that the Yankees couldn't remove him from the rotation, and he recorded a 3.13 ERA, 3.53 FIP, and 131 strikeouts in 21 starts during his first season.

Although the '98 Yankees romped to 114 victories, they trailed the ALCS two games to one against the Indians, and they were forced to ask El Duque to come up big for them in Game 4. He did just that, twirling seven innings of shutout ball, the first of seven straight victories the Yankees notched against the Indians and Padres, never losing another game en route to the World Series title. El Duque remained a rotation presence over the next four seasons, winning the 1999 ALCS MVP with 15 brilliant innings against the Red Sox, and helping the Yankees win two more championships in addition to the 2001 AL pennant. Dealt in a three-way trade to the Expos after the '02 season, El Duque returned from a season of injury to sign with the Yankees in '04 for an encore on another team that went to the playoffs. Over 136 starts with the Yankees, he pitched to a 116 ERA+ and put up 10.6 WAR. Not bad at all.

Still waiting on that dance, Coney.

7. Jason Giambi, 7/$120M, 12/18/2001

This one's going to be fun to hear about. While most Yankees fans unfairly view the "Giambino" as a bust who brought nothing but trouble with no championships and multiple PED whispers, others view his contract as one of the most surprisingly effective long-term deals of all-time. The son of a devout Mickey Mantle fan, Giambi rose to superstardom with the Oakland Athletics, with whom he won the 2000 AL MVP, finished runner-up in '01 to Ichiro Suzuki, and hit a ludicrous .338/.476/.653 with 81 homers and a 193 OPS+ over those two seasons. He had priced himself out of Oakland by the time he hit free agency after the '01 season, and the Yankees just so happened to have an opening at first base with fan favorite Tino Martinez hitting free agency.

So the Yankees decided to make Giambi their first baseman of the future over both Tino and rookie Nick Johnson. It was controversial, but dammit, his offensive production was worth it. He continued his high production in 2002, hitting .314/.435/.598 with 41 homers for a now-underrated Yankees team that had both terrific offense and pitching, winning 103 games. A shocking first-round exit at the hands of the Angels spelled the end for them, but they rebounded in '03 by winning the AL pennant as Giambi hit 41 dingers again and led the league in walks with 129. Some Yankees fans already viewed him as a disappointment though, as his batting average fell to .250, possibly due in part to the temptation of the short porch, but he was still quite good with a .412 OBP and a 148 OPS+. The '04 season was a nightmare riddled by his kinda-PED admission in spring training and a benign tumor that limited him to 80 games.

Giambi shook it off though, and over his last four seasons in pinstripes, he was fantastic with the bat, even as his already-shaky defense (I still have nightmares about his throws to second base) eventually shifted him to near-full time DH duty. Giambi won the AL Comeback Player of the Year award in 2005 thanks to 32 homers and a league-high .440 on-base percentage. From 2006-08, he was still a threat, batting .247/.386/.509 with 83 homers and a 131 OPS+. The Yankees never won the World Series with Giambi, but they missed the playoffs just once in his seven seasons. He was rarely the problem in the post-season, either, as he hit .279/.409/.510 in 32 playoff games. It was wise to move on from a soon-to-be 38-year-old Giambi in '09 (even though he somehow was still playing as a bench player on the Indians in 2014), but that doesn't mean Giambi was a Bronx bummer. He was superb, and I'll apologize for nothing including him in this top ten. Come back as hitting coach.

6. Goose Gossage, 6/$3.6M, 11/22/1977

You can tell it's a pretty awesome list when signing a Hall of Famer in his prime only makes seventh place. Goose's placement on this list can be debated, but his achievements certainly cannot. Signed to replace Cy Young Award winner Sparky Lyle as the team's closer in a controversial decision, Gossage got off to a slow start in '78, just as the rest of his team did. He rebounded in a big way though, ultimatley posting a 2.01 ERA and 3.00 FIP in 63 games and a remarkable 134 1/3 innings out of the bullpen. He led the league with 27 saves as well, and the Yankees ultimately roared back from a 14 1/2 game deficit to force a one-game playoff with their rival Red Sox, a tight affair at Fenway Park that ended when Carl Yastrzemski popped up a Gossage pitch. Gossage won the only World Series ring of his career that season, and he pitched six scoreless innings over three Fall Classic games to help the Yankees repeat as champions.

The Yankees didn't win another title with Gossage, though they did return to the playoffs twice. The only blemish on his record over the next five years was getting in a locker room fight with Cliff Johnson in '79 that ended up with him on the disabled list. Otherwise, he was outstanding, setting the standard for Yanekes closers that would not be equaled until a soft-spoken Panamanian named Mariano Rivera came along. "Bad to the Bone" blaring over the Yankee Stadium loudspeaker were the sounds of doom for opposing hitters, and Goose was an All-Star four times as a Yankee, ptiching to an all-time franchise-best 2.14 ERA in pinstripes and fanning 512 batters in 533 innings with his blazing fastball. It can be difficult for free agent contracts for relievers to pay off, but Gossage was undoubtedly the exception to the rule and a best-case scenario.

5. CC Sabathia, 7/$161M, 12/20/2008

Yes, the big lefty's contract does not look great now, but that is often the byproduct of such long-term deals. That doesn't change the fact that CC's original seven-year, $161 million contract turned out to be one of the best investments in team history. Sabathia was going to cost a pretty penny after winning the 2007 AL Cy Young Award with the Indians and just about single-handedly pushing the Brewers into the playoffs with complete game after complete game following his mid-season trade there in '08. The Yankees even had to include an opt-out clause that eventually led to an extension on the original year that hurts the Yankees at this point. Was it worth it though? Absolutely.

The Yankees were in dire need of a boost to the rotation following Mike Mussina's retirement, and CC clearly provided it. From 2009 through 2012, he was excellent for the Yankees, exactly the kind of ace they hoped they were getting. CC pitched to a 3.22 ERA (135 ERA+) and 3.28 FIP, averaging 226 innings and 32 starts per year. He was the workhorse they needed, and they made the playoffs for four straight years, winning the 2009 World Series title in great part due to CC's efforts. He shook off previous playoff struggles to win the ALCS MVP with 16 brilliant innings of two-run ball against the Angels, and though he lost the Fall Classic opener in a pitcher's duel with Cliff Lee, he rebounded on three days' rest in Game 4 to keep the Yankees in the game until Damon and Alex Rodriguez's late heroics. The Yankees don't get the 2009 World Series title without CC, and while he's hit hard times in recent years, his first four seasons should not be forgotten.

4. Hideki Matsui, 3/$21M, 12/19/2002

I don't think it's possible to meet a Yankees fan who disliked Hideki Matsui, and if one such person exists, I definitely do not want to meet him. After getting burned by Hideki Irabu, some fans were hesistant to accept the Yankees dipping into the Japanese market once again for a star, but the man they called "Godzilla" was absolutely up to the challenge. Although he rose to fame with the Yomiuri Giants in Japan for his prodigious home run totals, Matsui proved to be an extremely capable all-around hitter. In his age 29 rookie season of 2003, he hit .287/.353/.435 with 42 doubles and a 109 OPS+, helping the Yankees win the AL pennant. Matsui became the first Japanese-born player to homer in a World Series, even though the Yankees lost.

Matsui followed his impressive debut with a career year in '04, smashing 31 homers, posting a 137 OPS+ and 5.0 WAR, earning an appearance in his second straight All-Star Game. The Yankees didn't reach the Fall Classic that year or any of the next four, but that didn't stop Matsui, who literally played every game for them from Opening Day 2003 until mid-May 2006. After another terrific year in '05, he signed an extension that kept him in pinstripes through the '09 season. While injuries limited him to under 100 games in '06 and '08, he became a DH only in '09 and responded with a fantastic finale. He hit 28 homers with a 128 OPS+ in 143 games as the Yankees returned to the World Series, where Matsui secured his place in Yankees fans' hearts by demolishing the Phillies with three homers and a six-RBI performance in the Game 6 clincher.

Go go Godzilla.

3. Dave Winfield, 10/$15M, 12/15/1980

There must be a stigma against free agent Yankees on long-term contracts, because like Giambi and CC, Winfield has his detractors as well for some reason. But holy wow, was Winfield an outstanding player, and a Hall of Famer to boot. Signed to a then-record deal following the 1980 campaign, the former Padres star seized the spotlight in New York and posted eight straight awesome seasons in the Bronx. Winfield was always healthy, always an All-Star, and always productive, though he did so in such an understated manner that it could sometimes be overlooked by both fans and even the owner. The "Big Stein" never seemed to forgive Winfield for a sluggish World Series in '81, the only one he appeared in as a Yankee. That's a damn shame because just take a look at those aforementioned eight years:

Year Age Tm G PA H 2B HR BA OBP SLG OPS OPS+ TB
1981 29 NYY 105 440 114 25 13 0.294 0.360 0.464 0.824 139 180
1982 30 NYY 140 597 151 24 37 0.280 0.331 0.560 0.891 142 302
1983 31 NYY 152 664 169 26 32 0.283 0.345 0.513 0.858 138 307
1984 32 NYY 141 626 193 34 19 0.340 0.393 0.515 0.908 154 292
1985 33 NYY 155 689 174 34 26 0.275 0.328 0.471 0.799 118 298
1986 34 NYY 154 652 148 31 24 0.262 0.349 0.462 0.811 120 261
1987 35 NYY 156 655 158 22 27 0.275 0.358 0.457 0.815 116 263
1988 36 NYY 149 631 180 37 25 0.322 0.398 0.530 0.927 159 296

I mean... yikes. That's the kind of bat that reaches 3,000 hits, and 1,300 of them came as a Yankee, more than Winfield had for any other team. He crushed 235 doubles, 205 homers, hit .290/.356/.495 with a 134 OPS+, and notched 26.9 WAR. Alas, an injury robbed Winfield of his '89 campaign, and Steinbrenner's shady dealings with gambler Howard Spira in trying to dig up dirt on Winfield hung like a shadow over his final days in the Bronx. With Steinbrenner's suspension looming, Winfield was dealt to the Angels, and he finished his Hall of Fame career away from Yankee Stadium. Winfield absolutely deserved better treatment than he received, and it's just too bad Steinbrenner's disagreements with him led to Winfield choosing to wear a Padres cap in Cooperstown. Whatever. He was terrific.

2. Reggie Jackson, 5/$2.96M, 11/29/1976

In a way, Reggie might actually deserve the top spot on this list. Put aside all the controversy he caused off the field, and it's hard to imagine Reggie's five years in pinstripes going much better than they did. The Yankees were a team on the rise in '76, as they won their first AL pennant in 12 years, but they needed someone to push their offense over the top. Manager Billy Martin wanted Joe Rudi, which is just so silly in hindsight. Steinbrenner pushed GM Gabe Paul to bring in Jackson, who gained the national eye as one of the primary players on the A's teams of the early '70s who won three championships in a row. Paul went with Jackson, and the rest is history.

Obviously, the '77 season was just a mess in the clubhouse, as Jackson feuded with both Martin and beloved captain Thurman Munson for most of the year. Fortunately, the Yankees happened to have just a damn impressive team on the field that somehow won 100 games anyway, and Jackson powered the offense with 32 homers and a 150 OPS+. Like Matsui, he cemented his legacy in a World Series Game 6 performance for the ages, demolishing three straight homers to lead the Yankees to their first title since 1962. "Mr. October" was born. Another tumultuous year behind the scenes in '78 that even led to Martin's firing midsesason somehow ended with 100 victories again and another World Series title. Reggie wasn't the World Series MVP this time, but he more than did his part with two homers and an 1.196 OPS.

Jackson's final three years in the Bronx tend to be overshadowed by the championships seasons, but they were just fine as well. In 1980, he led the league with 41 homers and notched a 172 OPS+ finishing runner-up for the AL MVP to George Brett. Jackson departed for the Angels after another pennant in '81, but what a legacy he left: a .281/.371/.526 triple slash, 144 homers in just five years, 17.1 WAR, and a plethora of memories.

1. Mike Mussina, 6/$88.5M, 12/7/2000

Longtime readers should not be surprised that "Moose" sits atop this list. It would have been quite the challenge for anyone to come to a new city and accomplish what he did somewhere else, but that's exactly what Mussina did. After 10 awesome years in Baltimore, the Orioles did just about the equivalent of letting Hall of Famer Jim Palmer walk away in his prime when they failed to give Mussina much of an offer. Mussina took the hint and signed a long-term contract with the Yankees and wasted no time in pitching brilliant baseball in pinstripes. He struck out 214 batters in 228 2/3 innings and led the AL in both FIP and pitching WAR in 2001 with 2.92 and 7.1, respectively, but voters were captivated by teammate Roger Clemens's 20-3 season, so the Cy Young Award went to him. Silly.

The Yankees missed the playoffs just once during Mussina's eight seasons as a Yankee, and he quite often reached 30 starts and 200 innings. In 1,553 innings and 248 starts, he pitched to a 3.88 ERA (114 ERA+), a 3.50 FIP, struck out 1,278 batters, and walked just 1.8 men per nine innings. Mussina was among the most consistent starters in the league, reaching at least 3.0 WAR six times in eight years and hitting the 5.0 mark four times, finishing with 35.1 total as a Yankee.

Like Giambi, he was rarely to blame for the first-round exits, as he recorded a fine 3.80 ERA in the playoffs, striking out 92 batters in 97 innings. Derek Jeter's flip play overshadowed his seven shutout innings against the A's with the season on the line in 2001, and Aaron Boone's walk-off homer overshadowed his three brilliant innings of relief in another do-or-die showdown, Game 7 of the ALCS. Such was the nature with Mussina, who continues to be overlooked on the Hall of Fame ballot. Moose went out on top with a personal achievement, reaching the 20-win mark for the first time in his career, and he chose not to linger on while his performance faded. Don't listen to the doubters--Mussina was an all-time great Yankee and probably the best free agent signing they ever made.

Flip: Moose YEAH

Moose for Hall.