But as midnight passed, there was no word from either team, leaving two possibilities: The issue could be resolved by baseball commissioner Bud Selig, who said he would intervene if a deal wasn't struck by Tuesday; the other option would be for the teams to show they have made sufficient progress to request an extension from Selig.
"We've always felt like that was a possibility," new Red Sox general manager Ben Cherington said Monday of Selig's potential involvement as arbiter. "It's a difficult deal to work out. It's hard to quantify the value of a Theo Epstein. I have an idea of it, and Theo doesn't think he's worth as much as I think he is, and we haven't bridged that gap."
Epstein introduced his new general manager, Jed Hoyer, in Chicago on Tuesday afternoon and said that Selig might have to step in.
"There hasn't been a resolution yet," he said. "Either it will be turned over to Major League Baseball at the end of the day (Tuesday) and then baseball will go through their process, which will probably take a certain amount of time, or there will be an extension of the window for the clubs to continue to talk. It's not clear which of those two routes to take."
Although Cherington had chuckled when talking about Epstein's perceived value, the sides have yet to come to an agreement on what is meant by "significant" compensation, which is what the teams agreed upon when the Red Sox granted the Cubs permission to hire Epstein away as their president of baseball operations. Epstein had one year remaining on his contract as Red Sox GM.
Gordon Edes covers the Red Sox for ESPNBoston.com.