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Signing Manny Ramirez at the 2000 Winter Meetings signaled a new era in Red Sox history

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Coming off a fourth World Series win in 15 years, the Red Sox are firmly entrenched among baseball’s elite. Not only has the team been…
Coming off a fourth World Series win in 15 years, the Red Sox are firmly entrenched among baseball’s elite. Not only has the team been a regular contender in the playoffs, but also in the offseason in the pursuit of free agents.
Year after year, the Red Sox’ payroll ranks near the top of the league. And while some of Boston’s most important free agent additions (such as David Ortiz) were inconspicuous at the time, there have also been a parade of high-profile signings.
Few were more important or significant than that of Manny Ramirez on December 12,2000. The power-hitting outfielder agreed to an eight-year, $160 million deal (then a team record). Completed during the Winter Meetings, the signing of the 28-year-old was a Red Sox statement of intent following the Yankees’ fourth World Series win in five years.
And it almost didn’t happen.
Only days before, as the usual free agent scrambling was occurring during the Winter Meetings, it appeared Ramirez would be staying with his original team, the Cleveland Indians.
“The competition between the Red Sox and Cleveland Indians was at the end game stage late last night, and there were strong indications that the Sox were not going to get their man yet again,” wrote The Boston Globe’s Gordon Edes on December 11 .
In fact, Boston was already preparing a contingency plan in case Ramirez stayed in Cleveland. The scenario involved trading for Cubs slugger Sammy Sosa.
“We’re aware of it,” said then-Cubs manager Don Baylor to Edes.

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