Could one of those starters be Jon Lester? Though they traded the lefty back on July 31 for Yoenis Cespedes, the Sox have made their interest in bringing back Lester pretty clear.
Owner John Henry has met with Lester twice this winter in the lefty's hometown of Atlanta in hopes of making a reunion a reality.
But if Lester decides to go to the Cubs, Dodgers, Giants or perhaps a mystery suitor, Cherington and his staff will quickly attack Plans B, C, D and beyond.
The Phillies might trade Cole Hamels, who is due to earn $110 million over the next five years.
Max Scherzer and James Shields are both free agents. Justin Masterson started his career with the Red Sox, and he is a free agent who could be a good fit to return to Boston.
Even after investing in hitters Pablo Sandoval and Hanley Ramirez earlier in the winter, the Red Sox have the financial resources to make a move in free agency.
They also have plenty of depth -- both in the outfield and in their Minor League system -- to make some trades.
Though the Red Sox have said they'd like to keep Cespedes, FOXSports.com tweeted on Sunday that there were some discussions about a deal that would send the Cuban outfielder to the Padres for Ian Kennedy, and added that the Red Sox believe they can get an "even better pitcher" for Cespedes.
Aside from the main task of improving the rotation, the Red Sox have some more subtle moves to make.
Backup catcher is a priority, as Boston would love to add a left-handed bat to pair with starter Christian Vazquez.
But if the Sox can't find that left-handed bat, there's a chance David Ross could return for a third season in Boston. Everyone around the Red Sox respects Ross for his professionalism and leadership.
And now that Andrew Miller has signed with the Yankees, the Red Sox will ratchet up their search for a lefty reliever.
Stay tuned to redsox.com for news each day from the Winter Meetings, which officially begin Monday morning and will conclude at Thursday's Rule 5 Draft.
Cherington will meet with Boston's media contingent each day in San Diego. Manager John Farrell will hold his Winter Meetings availability on Monday, and MLB.com will have a full update on that.