Stripes or Sox? Rivals' biggest offseason moves

Christmas Eve marks anniversary of Contreras signing -- and birth of Yanks' 'evil empire'

December 18th, 2016
Jose Contreras helped the Yankees win the American League pennant in 2003. (Getty)

The Red Sox and Yankees boast one of the most storied rivalries in all of sports. For more than a century, the two franchises have met in 2,156 regular-season games and in three postseason series, compiling a rich history of competition.

On occasion, the rivalry has extended into the offseason, when the American League East foes have competed in a number of free-agency battles. Just this month, New York and Boston were among the teams vying for 's services before the free-agent slugger signed with the Astros.

Perhaps the most famous instance of these historic franchises facing off on the open market took place 14 years ago today. That Christmas Eve centered around Cuban hurler , a coveted free agent who defected from the island nation in 2002. Contreras' signing prompted Boston's team president, Larry Lucchino, to declare the Yankees as baseball's "evil empire."

"The evil empire extends its tentacles even into Latin America," Lucchino told the New York Times after Boston fell short in the bidding war for Contreras. The Red Sox had just finished as the runner-up to the Yankees in the AL East for a fifth consecutive season, and now New York had signed the right-hander to a four-year, $32 million deal.

Contreras' stay in New York was ultimately short-lived -- he was traded to the White Sox for Esteban Loaiza at the non-waiver Trade Deadline in 2004 -- but it was successful nonetheless. In his rookie season, he posted a 3.30 ERA through 18 games (nine starts) and helped the Yankees claim yet another AL pennant.

Contreras wasn't the first (nor the last) free agent to find himself courted by both the Yankees and Red Sox. These long-time rivals have enjoyed their share of success in recent years -- with the Red Sox holding the edge in championships since the turn of the century (3-2) -- but these offseason clashes have traditionally been dominated by the deep-pocketed Yankees.

"The Yankees have more resources than any other club in baseball," former Red Sox general manager Theo Epstein told the New York Times in 2003. "They're always going to be a force in the market. That's something other clubs have to deal with in developing strategies and executing them."

On today's anniversary of the birth of the "evil empire," here is a look at a few other notable free-agency bouts the Yankees and Red Sox have engaged in over the years:

Bernie Williams

For a time after the 1998 season, it seemed as if Williams and the Yankees were headed for divorce. Williams hit .339 that year, helping New York win 125 games (including the postseason) and the World Series. But the Yankees were ready to move on, as Boston appeared primed to outbid them for their star center fielder. The Yankees, in turn, targeted another free agent, Albert Belle, as a replacement. When the Orioles exceeded the Yankees' offer to Belle, then-owner George Steinbrenner surprised many observers by caving to Williams' demands to the tune of a seven-year, $87.5 million contract. At the time, it was the largest contract in franchise history.

The signing made Williams a lifelong Yankee. He remained in New York for eight more years, winning two more championships in 1999 and 2000. His No. 51 was eventually retired in '15.

Johnny Damon

After four stellar years with the Red Sox, the Yankees successfully wooed Damon away from Boston after the 2005 season. It was expected that Damon might be departing in free agency, but signing with the rival Yankees came as a surprise. New York bested the Red Sox's offer with a four-year, $52 million contract.

"They were coming after me aggressively," Damon told Boston radio station WBZ-TV. "We know George Steinbrenner's reputation. He always wants to have the best players, and I think he showed that tonight. He and [general manager] Brian Cashman came after me hard, and now I'm part of the Yankees and that great lineup. We're going to be a tough team to beat."

The Red Sox scored a victory in their 2006 offseason pursuit of Japanese pitcher Matsuzaka -- a rare instance of Boston prevailing over New York in competition for a free agent. The Red Sox eclipsed the Yankees and other interested clubs in the bidding war for the international star with a posting fee of just over $51 million. It took another $52 million to lure him to the U.S. on a six-year deal.

Matsuzaka played six seasons in Boston, going 50-37 with a 4.52 ERA in 117 games (116 starts).

The Red Sox were initially the favorites to land Teixeira when the first baseman became a free agent after a strong 2008 campaign. But the Yankees swooped in with an eight-year, $180 million deal that exceeded the nearest offer by more than $10 million.

Teixeira immediately rewarded New York's investment by hitting .292 with an AL-leading 39 home runs and 122 RBIs in his first season in pinstripes. He retired this past fall after eight seasons with the club, a tenure that included three Gold Glove Awards, one Silver Slugger Award, two trips to the All-Star Game and a second-place finish in the AL Most Valuable Player race in 2009, the year of New York's most recent World Series win.

After helping Boston win a World Series in 2013, Ellsbury left the franchise that selected him in the first round of the '05 Draft for the Bronx. The Yankees courted Ellsbury with a big payday, signing him to a seven-year, $153 million deal. The move came in the same week New York added catcher , another Red Sox target that offseason.

McCann batted .235 with 69 homers and 227 RBIs in three seasons with New York before he was dealt to the Astros last month in exchange for Minor Leaguers and . Ellsbury remains with the Yankees; he has hit .264 with 80 stolen bases and 32 home runs through 408 games since joining the club.

The Yankees spoiled Boston's efforts to reacquire reliever Miller prior to the 2015 season. The Red Sox dealt Miller and his expiring contract to the Orioles at the Trade Deadline in '14, but they were among the teams linked to the left-hander when he hit the open market the following offseason. Miller, however, instead opted for New York, where he signed a four-year, $36 million deal and continued as one of the game's most reliable bullpen arms through his trade to Cleveland this year.

"It wasn't an easy decision," Miller told MLB Network at the time. "I had some great offers that really humbled me and I was really appreciative of. Honestly, the Yankees offered some things that other teams couldn't. It was a good fit for my family, and I've seen firsthand what the Yankees are all about and what their goals are.

"It's something that I want to be a part of. I thought it was a great fit for me and a great chance to win."