The Adrian Gonzalez trade that would send the star first baseman from San Diego to Boston is now in jeopardy, as Gonzalez and the Red Sox were unable to work out a contract extension before a Sunday afternoon deadline. Gonzalez - who will make $6.3 million in 2011 - is set to become a free agent after the year, and the Red Sox want to get him locked up long-term.
However, while the trade doesn't look too good right now, it isn't completely dead, and there's still a possibility that Boston could pull the trigger. In order to do that, Theo Epstein and the Red Sox would have to be confident that they could still get Gonzalez signed.
Boston and San Diego are free to keep talking about the trade. The trade window didn't close - only the contract negotiation window did. It's possible that the Red Sox could agree to an exchange and then resume talking to Gonzalez and his agent again afterwards.
This would be a gamble, as the Red Sox would have already dealt a handful of prospects to San Diego. However, if they feel that they were close to reaching an agreement with Gonzalez before the 2pm ET Sunday deadline, or if they feel that an agreement could still be reached, then they could roll the dice and bring the first baseman to Massachusetts.