SAN DIEGO -- As Theo Epstein held court with reporters on Monday night at the Winter Meetings, a chalkboard stood behind his right shoulder. Any information that may have been scrawled across its black surface had been erased, though it seemed fitting that the board was blank at this stage of the Cubs' offseason.
Epstein, the Cubs' president of baseball operations, is currently in a kind of holding pattern as the top of the free-agent market shakes out. Members of Chicago's talented core group are potentially available via trade this offseason -- former National League MVP Kris Bryant included -- but some dominoes must topple for the landscape of suitors to really take form.
"Not even we know where it's going," Epstein said of this important offseason for the Cubs. "We know that there's things that we'd like to do. We don't know what's going to be possible for us, yet. It's an offseason where I think we have to be patient in a lot of ways.
"Free agency seems to be starting to move along, and then trades will come next. We're trying to stay on top of everything so that we don't miss an opportunity to get better."
That brings us to the major news of Day 1 of the Winter Meetings: Stephen Strasburg agreeing to re-sign with the Nationals on a seven-year contract worth a reported $245 million. That development did not directly influence the financially restricted Cubs, who are seeking rotation help but will be looking to trades or the lower tiers of free agency to address that need.
The Strasburg signing, however, might develop into the kind of domino that eventually leads to some scenarios written on a chalkboard by the Cubs' front-office leaders. Given the size of Strasburg's pact, the chances of Washington re-signing free-agent third baseman Anthony Rendon have likely decreased. That, in turn, could impact the market for Bryant.
Rendon and Josh Donaldson represent the top two free-agent third basemen available, with the Nationals, Phillies, Rangers, Braves and Dodgers atop the list of teams seeking help at the hot corner. Expect the Cubs to see where Rendon and Donaldson land, narrowing the list of possible landing spots for Bryant.
Bryant is a former NL MVP (2016), Rookie of the Year ('15), three-time All-Star and a key contributor to the Cubs winning the World Series three years ago. He is also headed for arbitration this offseason (MLB Trade Rumors projects his '20 salary to be $18.5 million), and he is on target for free agency following the '21 season.
The Cubs and any potential suitors for Bryant are also awaiting an arbitrator's decision about Bryant's service-time grievance, which could still be "a couple of weeks away," per Epstein. A ruling in Bryant's favor would make him a free agent next offseason rather than two winters from now, impacting the type of return Chicago could potentially net via trade.
"We're fairly confident in what the outcome is going to be," Epstein said. "It'd be nice to have that final confirmation, but I think we're operating with what our understanding of what the likely outcome will be and moving forward that way."
Right now, the Cubs are trying to balance contending in the present with the realities of future seasons. There is also the issue of the team's 2020 payroll projection, which is in the neighborhood of $200 million before any additions. The first luxury-tax threshold is $208 million, meaning that trades are likely needed in order to give Chicago more financial flexibility for any impact acquisitions.
In Monday's discussion, Epstein maintained his stance on not revealing the ceiling of the Cubs' payroll.
"We never point to where we expect to end up in terms of our payroll," Epstein said. "And this year particularly, there's a lot of strategic reasons with what's going on out in the marketplace to play our cards close to the vest."
Barring any extensions, Bryant is not the only star on the roster on a path toward free agency. As things currently stand, shortstop Javier Báez, outfielder Kyle Schwarber and first baseman Anthony Rizzo could hit the open market after the ‘21 season. Catcher Willson Contreras could follow them after the ‘22 season. They could all be back in '20, but the Cubs are open to exploring alternatives.
Among that group, Bryant and Contreras have generated the most intrigue this offseason.
"I know we're not going to force anything. We're not going to make change just for change's sake," Epstein said. "I do think we can benefit from some change in certain areas. We are interested in pursuing some opportunities -- opportunities to get better immediately and opportunities to make our future healthier as well -- but you can't force anything.
"You have to be realistic about the market that you're in and what opportunities come, but there are a lot of promising leads out there. Obviously, we haven't gotten anything to the point of consummating a deal yet. But we're at the early stages of the offseason."