The Cowboys will have to decide whether to keep or cut Free by the fifth day of the 2014 league year because the right tackle’s $3.5 million base salary becomes fully guaranteed. If Free returns to the form that earned him the $8 million a year contract in 2011, then the Cowboys have a bargain. If he does not, then the Cowboys will have to deal with some cap issues and find a replacement.
While Free will/could make $3.5 million in each of the next two seasons, the final two voidable years of the contract he signed in 2011 do not disappear, creating the potential cap complications. The Cowboys will have to account for signing bonus proration in 2014 and/or ’15 whether Free is on the roster or not.
If Free plays the next two seasons, then he will count $3.98 million against the cap in 2015.
If the Cowboys cut Free before the fifth day of the 2014 league year and designate him a post-June 1 cut, then he would count $3.02 million against the cap in 2014 and $3.98 against the cap in 2015. If they chose not to put a June 1 designation on the cut, then the move would cost the Cowboys roughly $500,000 in room. Because the Cowboys will need the room next year, Free would almost assuredly be a June 1 cut if the club would go that route.