And that is when the Red Sox might start getting some more answers with regard to the free agent from their 2009 team they would most like to retain.
While the Red Sox had exclusive rights with outfielder Jason Bay until free agency began, it has been clear from the outset that the star left fielder won't sign until, as Epstein put it several times, he goes "through the process."
For Bay, that process is being out on the open market and seeing if his best fit is to stay in Boston or move on. And that is also part of the process for the Red Sox, as they determine how their perceived value of Bay compares to other teams around the Majors.
"We'd love to have him back," said Red Sox president/CEO Larry Lucchino. "He's, in may ways, the personification of the type of player we want here."
To no surprise, Bay's willingness to test the market became even more clear on Thursday, when SI.com -- attributing "sources" -- reported that the outfielder turned down a four-year deal worth "close to $60 million," which ensured he'd hit the open market on Friday.
Both the Red Sox and Joe Urbon of CAA, who represents Bay, chose not to confirm or deny the SI.com report. The sides have had open dialogue for months and have both tried to keep matters as confidential as possible.
Neither side has set a deadline at this point of the game.
"It lasts as long as it lasts, until one side goes and does something different," said Epstein. "I think this part of the process is important to him. He'll see what it's like and see what's out there and ultimately make the decision. We've maintained dialogue -- yeah. All along, we've maintained he was going to go and see what's out there. We'll see. He's a priority."
Urbon has spent the past couple of weeks putting that process in motion.
"I guess the best way to put it, these last couple of weeks have really confirmed for us and for Jason what we anticipated, and that is that a number of clubs have Jason really at the top of their priority list and consider him a must sign," Urbon said. "I think that's what we've gleaned over these last couple of weeks. Certainly no offers have been made.
"The theme that we've conveyed and has been well accepted when we've had these conversations with clubs is that this is a consistent and durable run producer who fits so seamlessly in the middle of a lineup, and really so perfectly into the clubhouse, [and it] is what a lot of clubs are looking for to sort of find that last piece of the puzzle that might lead them to the postseason and put them in a better position to be in a World Series opportunity.
"That's kind of what these last two weeks have really confirmed for us. I guess the rubber hits the road after midnight Thursday night when clubs do have the ability to start making financial offers, but until then, I think we feel pretty good about at least where other clubs see Jason in terms of the free-agent market."
And where do things stand with the Red Sox?
"We've had some continuous, candid, consistent dialogue since Spring Training," Urbon said. "I feel like they, too, believe Jason Bay is a priority sign for them. He's a perfect fit. He replaced a Hall of Famer in left field [Manny Ramirez] and did it seamlessly. He's enjoyed where he's played, he's enjoyed the fans. Everything about his experience this year and a half has been ideal. The Red Sox have recognized that, they've acknowledged it and they've made it known that he's a priority, and I don't think that will change after Thursday.
"At this point, [Jed Lowrie] has to prove his health. He's not someone we can depend on right now. I think, ultimately, he will be. But until he proves his health, we can't let the season hang in the balance."
-- Theo Epstein
"They haven't put their best foot forward in terms of an offer, and I anticipate that they will, sooner rather than later. When they do, we'll know it -- they'll let us know that, and we'll have a decision to make. Right now, we're not in that decision-making mode by any means."
"There's two parties to every negotiation and every potential signing," said Epstein. "Needs change and holes get filled and you move on. As long as you maintain good dialogue and neither party gets caught by surprise, it's reasonable to extend things. We're not even close to the Winter Meetings yet."
The Bay issue is a big one for Boston. If the Sox aren't going to be able to keep the left fielder, they must go out and find another big bat to take his place.
Could that be Matt Holliday, a fellow free-agent left fielder with similar credentials?
Will the Red Sox conduct negotiations with Scott Boras, who represents Holliday, before closing the book on Bay? Or will they exhaust negotiations with Bay first? Epstein did discuss multiple issues with Boras at the General Managers' Meetings in Chicago, including Holliday.
One of the most fascinating aspects of the next several weeks will be how Bay's negotiations with the Red Sox or other teams will play off Holliday, and vice versa.
But the left-field dilemma is just one of several intriguing plots Epstein and Co. will be tackling during this Hot Stove season.
Who will play shortstop for manager Terry Francona in 2009? The Red Sox declined the $6 million option on shortstop Alex Gonzalez, but haven't ruled out bringing him back as a free agent at a lower rate of compensation. Marco Scutaro, who blossomed for the Blue Jays in 2009, is the top shortstop on the free-agent market. Because of his Type A status, the Red Sox would have to compensate that signing with draft picks. Orlando Cabrera is also a Type A free agent, which makes a return stint to Boston highly unlikely for the '04 hero.
One intriguing free agent who wouldn't require any compensation is Omar Vizquel, a potential Hall of Famer. Though he is 42, Vizquel could help in a supplemental role. The Red Sox are uncomfortable with banking on Jed Lowrie for the starting role because of the switch-hitter's injury woes. If they had some quality insurance such as Vizquel, perhaps it is a situation that would work for everyone. At this stage of the game, Vizquel is more of a part-time player.
"We're going to acquire somebody to be our shortstop. At this point, [Lowrie] has to prove his health," Epstein said. "He's not someone we can depend on right now. I think, ultimately, he will be. But until he proves his health, we can't let the season hang in the balance. We can't allow ourselves to have instability at shortstop again if he's not able to answer the bell health-wise. I think he will get to the point where he can demonstrate his dependability and his health. We're not going to rely on good offseason reports. He has to show up and do it day in and day out before we rely on him. So yeah, we'll be acquiring a shortstop via trade or free agency."
Though the Red Sox are fairly comfortable with the way their pitching stacks up, they've already had some discussions regarding John Lackey, the Angels' ace who is now a free agent. However, Boston would be breaking from its recent tradition of not signing pitchers in their 30s to long-term deals if it outbid the competition for Lackey.
Of course, the Red Sox never limit themselves to the free-agent market. Epstein is always active when it comes to trades. You can be sure that the club will have plenty of discussions with the Blue Jays about ace Roy Halladay, not to mention the Padres regarding slugging first baseman Adrian Gonzalez.
Epstein is open to making significant changes, but he doesn't feel as if it is a necessity. He will gauge the market and see if the opportunity is there to make a major signing or trade.
"I think it could go a number of different directions," Epstein said earlier this offseason. "I think we're always open to change, because I think you need change to improve as part of the natural cycle in baseball and in life. Sometimes the market doesn't bear that out."