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Breaking the 86 year drought with the Boston Red Sox?  Try ending one over 100 years old. Theo Epstein, the man who became the youngest GM in the history of major league baseball back in 2002, signed with the Chicago Cubs today on a deal worth 20 million dollars for the next five years.

Epstein will soon find out, the NL isn’t the AL, and Chicago, especially the Cubs, are a very different beast from what the Boston Red Sox were when he took charge, being the front office face as the team arguably became the best in the AL and won two World Series titles.

Boston finished over .500 for five straight years before Epstein, finishing second, behind the Yankees, each time. They made the playoffs twice. Not prime material, but certainly, there was plenty to work with. Cubs? They’ve finished 5th in the NL Central the last two seasons, winning a total of 146 games. But lets talk future, financial future, possibilities.

New owners might be great, but there’s rebuilding to be done, contracts to get rid of. Alfonso Soriano, for example. He makes 19 million dollars and is owed 54 for the next three years. Same with Carlos Zambrano, once the face of pitching in this organization, now someone who doesn’t look like he’ll be playing the game for much longer.

Epstein, despite being from the money-ball GM-tree, had lots of cash to play with in Boston. Usually the team with the second highest payroll in the league. The Cubs aren’t the Marlins, but their potential to generate a huge income, right now, due to Wrigley Field being what it is, is limited.

The good thing? No pressure, or far less of it. Boston is a rougher town to be in, in terms of sports fans and especially sports media. Not winning anything in over a century and not being really close to it except for one time in 2003 does take the edge off the demands for a World Series ring. There’s a reason no one called the Red Sox “Lovable losers“.

The Brewers don’t look like a team that’ll hang on to their big guns, especially Prince Fielder after these playoffs. The Cardinals? Old. Experienced, but in dire need of a revamp. Things might be changing in the NL Central, but I don’t think it’ll be quick as it was in Boston. A whole of a lot less to build on.