The Yankees have been after Headley for years. They eventually acquired him for pennies on the dollar, which wasn't how it was supposed to be.
One of my favorite factoids of the past few years: In 2012, Chase Headley led the National League in RBI, while playing for a bad team in Petco Park. I know RBI aren't in vogue, and they never will be again, but don't look at that as a way to evaluate how good Headley was. Look at it as a way to describe what happened, how magical he must have seemed that year. It's more than a little surprising that the 2012 Padres had 115 base runners, yet that's how many times Headley drove in a run that season. It was 18 percent of the team's season total.
That was peak Headley, He finished fifth in the MVP voting, but probably deserved to be higher. He won a Gold Glove, too, for good measure. He was a star. The Padres were going to build their organization around him. Instead, they traded him two years too late, getting a fungible utility player and a pitcher who was ranked as the Yankees' No. 15 prospect in a bad farm system by Baseball America. It's not exactly Ozzie Smith for Garry Templeton, not yet. But it still has to sting.
Bad team + good player = omnipresent trade rumors, and Headley rumors seemed like a permanent fixture on the baseball landscape. With the help of the MLB Trade Rumors archive, here's the progression of Chase Headley rumors to the present, sordid reality.
The Beginning
The Padres are so high on Chase Headley that MLB.com's Corey Brock says the team once turned down a deal with Pittsburgh that would've brought Nate McLouth and Xavier Nady to San Diego.
March 1, 2010
Headley was a nice player at this point, a two-year player with just one full season on his ledger and a career OPS of .740 (104 OPS+). The Padres were wise to be patient with him, as he was a top-20 prospect in baseball according to most outlets just two years earlier. Both McLouth and Nady had value back then, so it wasn't an easy trade to dismiss, I'm sure.
The Refusal
For now, sources say the Padres will be reluctant to move Headley. But the team is coming off a 91-loss season and has a new general manager. So stay tuned.
Nov. 12, 2011
This was before the breakout season, and the Padres figured they were going to be selling low. They were right. Pundits figured they were willing to shop him early because of Logan Forsythe and James Darnell, but the Padres were uncomfortable with that idea for some strange reason. Until they had to, they were going to ask for every last prospect from every team bold enough to check in on Headley.
#Padres are and will ask for the moon on 3B Chase Headley. Doesn't mean they won't move him. It means it will cost a lot if they do.
— Corey Brock (@FollowThePadres) December 5, 2011
The Frenzy
The Dodgers, Pirates, Indians, Orioles and Diamondbacks are among the teams believed to have some interest in Padres third baseman Chase Headley, Jon Heyman of CBSSports.com reports. The Padres are open to trading Headley within the division, Heyman adds.
July 5, 2012
Other suitors listed before that trade deadline: Phillies, Mariners, A's, and Yankees. The A's wouldn't part with Dan Straily, reportedly, and the Orioles wouldn't deal Jake Arrieta.
Those names aren't exactly impressive in retrospect, even with Arrieta's breakout season for the Cubs, but the Padres could have extracted a Pence-like deal from the Phillies, getting someone like Jonathan Singleton. The A's probably weren't eager to give up their best prospects like Straily or Brad Peacock, but there was a first-rounder by the name of Sonny Gray who could have sweetened the pot on a deal.
With 10 to 12 teams interested, it isn't irresponsible to think there were some sweet deals offered. Jon Heyman wrote the Pirates made a serious push, and they had the prospects to do it. Gerrit Cole, maybe Gregory Polanco ... they're not Yangervis Solarte and negative money, but who is?
The Commitment?
The Padres have had some extension talks with Chase Headley, Olney reports. While both sides are interested in a deal, it’s hard to value Headley following his impressive second half performance.
Nov. 5, 2012
Bill Center of the San Diego Union-Tribune believes it would take at least four years and $36-40MM to extend NL MVP finalist Chase Headley.
Nov. 11, 2012
The Padres had "very rough" extension talks with Chase Headley earlier this year and would like to keep him long-term, writes Scott Miller of CBS Sports. There's no great urgency since he's controlled for two more seasons, GM Josh Byrnes said Monday, but they'll continue talking over the winter and could work something out in the spring
Dec. 4, 2012
A guess: Headley's total contract this offseason will still be worth more money than what would have been left on any extension signed after 2012. He didn't have the leverage of free agency, and there would have been some give and take when it came to buying out free agent years in exchange for increased salary during his arbitration years.
The Blockbuster That Wasn't
The Padres and Diamondbacks have had on-and-off discussions about a deal involving Justin Upton and Chase Headley since July, according to Ken Rosenthal of FOX Sports. However, those talks have yet to result in a deal.
Jan. 5, 2013
The Padres could have had Justin Upton, possibly. That would have been fun to write about. The Diamondbacks were reportedly asking for additional pieces, though, so nothing transpired.
I wonder if Diamondbacks would have preferred Headley to Martin Prado, who's been a touch disappointing for them.
Confusion
The Padres haven’t settled on a long-term strategy for handling Chase Headley, but they aren’t going to trade him any time soon.
March 11, 2013
Headley wanted to be paid like a star. The Padres wanted other teams to offer up prospects as if he were a star, but they were never that interested in paying for him like a star. They said they were, at one point.
"Will it be 10 years? No," said (Padres executive chairman Ron) 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."
May 2, 2013
That led to a surprised reaction from Headley, who said, "To be honest, this is not something we've discussed."
May 2, 2013
But they never came close to satisfying Headley's demands. These extension talks (or non-talks?) came after a thumb injury, but before a subpar 2013 season. A late-season surge from Headley made things even more confusing for both sides.
Conclusion
The Padres haven't had any extension talks with Chase Headley this offseason, and as it stands right now, there are no plans to begin negotiations.
Nov. 13, 2013
"We're hoping he'll have a breakout season," the Padres didn't say. "So he'll have more value at the deadline. What's the worst that can happen, he's terrible and we get Yangervis Solarte for him? Ha ha, yeah, sure. Maybe we'll send money over in the deal. Ha."
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In the span of a thumb injury and a season-and-a-half of disappointing performance, the Padres lost everything. They wanted to see what was in the box. They gave everything up to see what was in the box. The box was filled with Padres. The former GM regime could have dealt Headley for something sweet, something franchise changing. They waited far too long.
Of course, they could have dealt him for something that already looks comically unfair. While it's fun to look at this list of top-100 prospects from before 2013 and start placing the best players on the Padres, there was a strong chance they were going to end up with an enigma like Trevor Bauer or Danny Hultzen, because that's how prospects work.
All that we know is that if the Padres were going to trade Chase Headley all along, they sure picked a lousy time to do it. After years and years of rumors, involving the best prospects in baseball, the Padres got a utility player and a 15th-ranked prospect, and they had to pay the Yankees to get that much.
What a strange, unfortunate turn of events for a franchise that probably should have had its own Mark Teixeira trade. Everything looks worse with hindsight, but it's hard to believe the Padres didn't choose between dealing Headley or aggressively attempting to lock him up after his incredible 2012. They chose to do nothing. Now they have Yangervis Solarte. That's some bizarre alchemy, alright.