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Living in Las Vegas, I'm sometimes out of the loop on Red Sox news. I'm just now learning that Epstein's contract ends soon and there are problems in the negotiations.
Boston Globe article
What's the word in Boston?
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Buster Olney was on WEEI (the Boston sports radio station) the afternoon (around 1:00 PM) claiming that the reports about Epstein and the Red Sox being far apart were overstated, and that a deal is close - other guys on WEEI were reporting that the Red Sox were waiting for the World Series to end to announce a deal; however, the Boston Globe owns part of the Boston Red Sox and it's possible that have contact with the best sources available.
IMO, there's probably a 75% chance Theo returns, if I had to give a rough estimate - and there's been speculation that were he not to sign a deal with Boston, he might leave baseball altogether, as he has a Yale law degree and has connections in entertainment, business, and politics.