12:55pm: Headley tells MLB.com's Corey Brock that he is "flattered" by the concept of an offer and loves playing in San Diego, but makes it clear that he and his agent do not want to negotiate an extension during the season:
"We made it abundantly clear [before] that we didn't want to talk about it during the season. I didn't think that for me and for the team that it was good to get caught up with all of this during the season."
Headley made a point to say that he hopes the two sides can revisit negotiations after the 2013 season, citing a love of the fans, the city and the way he's been treated by the organization since he was drafted in the second round in 2005.
11:01am: The Padres aren't a team that is known for issuing massive contracts, but it appears that the team's new ownership is willing to change that perception in order to retain Chase Headley. Padres executive chairman Ron Fowler told Bill Center and Chris Jenkins of the San Diego Union-Tribune that by midseason the team offer Headley a multi-year contract that would make him the richest player in franchise history:
"Will it be 10 years? No," said Fowler. "We're not going to do something like that. But we will do an offer that will be the largest offer we've ever made to a player in San Diego history and think it will be very close to some of the numbers I read in the press."
Jake Peavy currently holds the Friars' franchise record for largest contract with a three-year, $52MM deal signed back in 2007. That was on top of a pre-existing $14.5MM contract with an $8MM club option, bringing the total Peavy commitment to $74MM for the 2005-12 seasons.
Headley is further along in his arbitration years than Peavy was at the signing of his extension, so the Padres will need to pay closer to market value for Headley's free agent years. The 28-year-old Headley is controlled through the 2014 season but told Center and Jenkins that an extension will require a lengthy commitment:
“A three-year deal would put me in the same position I am now in about a year and I don’t want to do this again,” Headley said.
I agree with the Union-Tribune duo in speculating that any extension for Headley would need to cover at least the next five seasons. Comparables for a Headley deal could include Evan Longoria and David Wright, both of whom signed extensions this offseason that valued their free agent seasons at roughly $17MM each. Assuming a $13MM salary for Headley's final arb year, an extension covering the 2015-18 seasons would cost $81MM at that rate. If Padres GM Josh Byrnes is able to secure a club option at $17MM for the 2019 season with a $4MM buyout, a five-year $85MM extension similar to the one Andre Ethier signed a year ago seems feasible.
Headley's agents at Excel Sports Management could push to make him the Padres' first $100MM player by increasing the guaranteed commitment to six seasons with a hefty buyout on an option for a seventh year. While Headley lacks the track record of most $100MM players, he's continued his 2012 production early this year. Another two months of elite production could help the case.
Back in August, majority owner John Moores sold the Padres to a group headed by Fowler and several members of the O'Malley family, who previously owned the Dodgers. It's possible that the new ownership, who purchased the team for $800MM, could use Headley as a way to begin a legacy and show the fans a commitment to winning.