Drew is looking for a multiyear contract and has found the market to be unfavorable, thanks at least in part because any team that signs him will have to give up a draft pick. The Red Sox made him a one-year, $14.1 million offer and he turned it down, thus adding the pick to his free-agent price tag.
"We've kept a dialogue going, and frankly haven't had a conversation in a little while now. It was probably just before the holidays," Cherington said on WEEI's Hot Stove show Thursday night. "I don't have any doubt that Stephen has opportunities out there. He's a good player. He's a healthy player. He's going to be someone's shortstop this year.
"We think we've had an honest, open dialogue with Stephen and Scott obviously about what our interests are and some of the issues that we're facing, he's done the same and we'll continue to have a conversation as we always do with Scott. But there's nothing really to report on it."
As the waiting game continues for Drew, Cherington said he has not set a deadline for when the team would move on without him. If Drew returns, it would likely move rookie Xander Bogaerts to third base and leave fellow infielder Will Middlebrooks in limbo.
Cherington also pointed out the value of an organization committing to young players instead of signing free agents. Both Bogaerts (21) and Middlebrooks (25) are under organizational control for multiple seasons.
"We have, as everyone knows, got a handful of young players who we believe in, who we believe are going to be really good major league players," Cherington said. "Of course, when they're unproven at the major league level, there's always a fair question about transition and whether there's any sort of learning curve that needs to take place. That said, if you have young players you believe in, there is a real value to be obtained from committing to some of them, because if you don't, you never do.
"Everyone knows the best teams year in, year out are ones that can integrate young players from time to time and integrate them successfully, because that makes your team better, it helps you manage things, it helps you manage payroll year in, year out. The only way to do that is to at some point commit to the young player. The question is which players and how many and what is the right time to do that. That's the dialogue we've been having internally. We think we're in that position that we have a chance to do that."
Cherington also said the "door will be open" for contract talks between the club and designated hitter David Ortiz through the course of spring training and into the season.
The 38-year-old Ortiz, who will make $15 million on the final year of his contract in 2014, said last month that he had been in touch with the Red Sox to express his desire for a new deal that goes beyond this season.
"It's important to me, it's important to ownership, important to the organization to have open dialogue with our key players," Cherington said. "And David is certainly one of those. We've talked this winter."
Ortiz is coming off a playoff run in which he hit .353 and had five homers and 13 RBIs en route to being named World Series MVP.
"Maybe I'll play another year or two more years," Ortiz said in December at his charity golf tournament in the Dominican Republic. "I'm at a stage where I'll play depending on how I feel physically."