For a struggling Red Sox team, the story of the season has been Jon Lester's expiring contract.
If Lester walks, where to the Red Sox turn?
"They don't have plan after Lester," said Tanguay. "You've got Workman, you got De La Rosa, Webster has been a disappointment, Clay Buchholz is not the ace we thought he was going to be. They don't have anybody to take his spot."
Dan Shaughnessy believes if the Red Sox want to get a deal done, it has to happen during the season.
"If they let this thing get into the offseason," said Shaughnessy. "They're going to have a lot of bidding and it's going to be hard for them to hold their position on not giving out big years and big dollars.