San Diego's first objective is to keep Headley, likely their best all-around player, long-term. However, the sides have never before come close to striking a deal, so even with ownership's promise to offer him the biggest contract in Padres history the chances to do a contract wouldn't necessarily seem to be all that great.
The Padres' record contract is the $52 million, three-year deal for pitcher Jake Peavy. The offer for Headley would have to be considerably more than that to have any hope of swaying him.
Should Headley hit the trade market, there would presumably be teams lining up for him. Third base is a hard spot to fill, and he has shown to be a pretty good two-way player, albeait one who didn't come close to matching his career year of 2012 this past year. The Padres could also keep him, then take the draft choice when he becomes a free agent next winter.
Headley followed his fifth-place finish in MVP in 2012 with totals of 13 home runs, 50 RBI and a .250 batting average this past year. In '12, he had 31 home runs, 115 RBI and a .286 batting average, while winning his only Gold Glove and Silver Slugger awards.
Padres ownership tried to sit down with Headley during last season, but he said he preferred to concentrate on the season. It didn't go exactly as planned though. After starting the year on the disabled list, he came back quickly but never got close to his '12 performance.