First up is the easiest to fathom—Phil Loadholt.
Phil Loadholt might have the hardest contract to predict. He's had an up-and-down career, but ranked as the seventh-ranked right tackle by Pro Football Focus. In 2011, he was a dominant run-blocker but a very weak pass protector. The opposite was true the two years previous. An enigmatic tackle who may have finally come into his own this year in all phases of the game, he could command less than he's worth.
Free agent right tackles have had a number of deals offered to them, making Loadholt a particularly difficult puzzle to solve, but there's a good chance his cap hit for 2013 would be between Tyson Clabo's 2012 hit ($4.8 million) and Todd Herremans' hit ($3.7 million).
Clabo had an extraordinary 2011, so it is more likely that Herremans' deal will match Loadholt's. A 5-year, $28 million deal that has a $6 million dollar signing bonus with $8 million total guaranteed makes sense. The low guaranteed total is to ensure a safer deal from an inconsistent player. That should make Loadholt's cap hit $4.3 million in 2013.
Loadholt played like a very good right tackle, but still has penalty problems and cannot prove that he plays well consistently. I have given him the bottom of the high-end right tackle deals.