The Red Sox and Rockies were expected to continue their discussions on a possible Todd Helton deal on Monday.
While discussions have been ongoing, there's a major hurdle to overcome. Which of the prospects coveted by the Rockies would the Sox be willing to give up in addition to Mike Lowell and Julian Tavarez? Among the players Colorado likes include Craig Hansen, Manny Delcarmen, Clay Buchholz, Jacoby Ellsbury, Daniel Bard and Jon Lester.
One of the six the Sox might consider dealing is Delcarmen, but Theo Epstein doesn't appear to be keen on giving up any of his young pitching and that's where the deal could die.
There are also seems to be a mixed bag of opinion in the Sox organization on whether the team should take on five years of Helton, though there are others who feel he'd be an incredible piece to add to an already good lineup.
The Sox would also have to do their due diligence with Helton's back issues. The Sox would have to receive Helton's medical records and he would have to be examined much like the J.D. Drew situation to determine whether the back problems are anything that will continue to diminish his power.
According to sources involved in the talks, there's still not a firm number on how much of Helton's contract the Rockies would absorb, though it could be 50 percent of the $90.1 million remaining or even more depending which prospect, if any, heads to Colorado.
Helton told the Denver Post that he would waive his no-trade deal to Boston. He would also wave it to Atlanta or St. Louis. But Helton is enamored with joining the Red Sox, a team he feels can make it to the post-season and win a World Series.
The other issue is some bad blood between the two teams over the failed Larry Bigbie deal of a couple of years back. While some believe that's smoothed over, others believe there might be some lingering feelings. But according to one source, "It's really not an issue if they can make a deal." .