Why the Padres Should Have Kept Chase Headley

Last week we (somewhat) briefly discussed the surprisingly anticlimactic end of the Chase Headley saga in San Diego, the unexciting return brought back from the New York Yankees for his services, and the fact that, inexplicably, the Padres had to send $1 million to the Bronx to complete the deal.

The Headley contract situation went about as badly as it could have for the Padres (and arguably for Headley, too), as they played it year-to-year and both failed to keep him around long-term and failed to trade him when he had a legitimate spike in value immediately following his 2012 breakout. In the end, tails between their legs, the GM-less Padres dealt him to New York for a 27-year-old utility infielder and a 23-year-old starting pitcher (who is projected as a future reliever) still in high-A ball.

At one point in my article last week, I wondered, “Why wouldn’t the Padres just hold onto Headley and give him a qualifying offer for $14-ish million this offseason?” Upon further reflection, that seems to be a subject that deserves additional examination. If the market for the third basemen’s services had sunken to the depths of a Yangervis Solarte/Rafael De Paula return combo … why not hold onto Headley?

There are at least a few reasons why keeping the third basemen around would have made sense.

The Padres do not have a general manager

Sure, after Josh Byrnes’ mid-season firing, AJ Hinch, Fred Uhlman Jr., and Omar Minaya are acting as the GM until a replacement is hired, but none of the three were serious contenders to take over that position full-time. And with the final four candidates apparently narrowed down to Mike Hazen, Kim Ng, AJ Preller, and Billy Eppler, it’s likely that the next Padres GM is currently working outside of the Padres front office.

That said, it’s not as though the Padres baseball ops department can simply close up shop for a month or two and wait for ownership to make its decision. You see, that’s the problem with firing your GM mid-season, prior to a trade deadline when your team, despite its season-long struggles, has plenty of valuable pieces for sale. Some big decisions have to be made with an interim GM stable in place, something you’d rather avoid when possible.

Of course, some moves can wait, and if the best return the Padres could muster for Headley was the one they got back from the Yankees, it might have made more sense just to hold onto him for the remainder of the year and let the new GM decide whether to hand him a qualifying offer in the offseason or simply let him walk.

Chase Headley’s value is at an all-time low

With just over two months left until free agency and in the midst of his worst offensive season, it’s not hard to see why the rest of baseball wasn’t willing to part with a prized prospect for Headley. Add to the offensive struggles* the fact that Headley’s now on the wrong side of 30 and has hit the disabled list in three out of the last four seasons, and his trade value only plummets further.

*Headley’s finally coming around, hitting .330/.330/.489 in 88 July plate appearances (small sample size alert!), though his 23 strikeouts and 0 walks in the month are simultaneously amusing and concerning. His current slash line, which includes his hot start with the Yankees, is up to .238/.300/.371.

How much surplus value did Headley have when the Padres dealt him? If we estimate Headley as a true talent 2.5 WAR player and the value of a marginal win on the free agent market at $7.5 million (we’re just spitballing here), that puts Headley’s market value at something like $19 million. Once you account for the two-plus months left on Headley’s contract, his surplus value sat somewhere around $3 million at the time of the trade.

You can play with those numbers and come out with different figures, but the point is clear. Injuries, sub-par recent performance, Petco Park, underrated fielding ability, a 2012 breakout that looks like a blip on the radar, and impending free agency were probably all factors that led to a lukewarm trade market for Headley. And the package of Solarte and De Paula, while underwhelming, was about all you could reasonably expect in return.

A qualifying offer still made perfect sense

In an interview with Darren Smith, AJ Hinch noted that the Padres were leaning toward not offering Headley a qualifying offer (QO) in the offseason. The only logical explanation for not offering Headley a QO — and Hinch (sort of) went on to explain it — is that the Padres were afraid Headley might accept it and delay his free agency, leaving the Padres to pay him somewhere in the neighborhood of $14/15 million next season. (The QO figure is based on the average of the top 125 paid MLB players. Last year, it was $14.1 million and this year it projects to be somewhere in that range.) If Headley declined the QO, which is what all 13 players did last year (some unwisely), the Padres would have received a compensatory draft pick at the end of the first-round.

Both of those outcomes — Headley accepting the QO and sticking around for another year or him declining it allowing the Padres to pick up an extra early draft pick — would have had their benefits. While $14 or $15 million might seem like a lot for Headley at this point, it really isn’t. Last year, a number of players with similar or significantly less robust track-records than Chase Headley were given QOs — Stephen Drew, Kendrys Morales, Ubaldo Jimenez, Mike Napoli, Ervin Santana, Nelson Cruz, etc. Further, consider some of the deals signed on the free agent market last year:

Player Team rWAR 2011-2013 Deal
Scott Feldman HOU 2.1 3YRS, $30M
Curtis Granderson NYN 9.7 4YRS, $60M
Ubaldo Jimenez BAL 1.9 4YRS, $48M
Mike Napoli BOS 11.4 2YRS, $32M
Jhonny Peralta STL 8.1 4YRS, $53M
Carlos Beltran NYA 10.9 3YRS $45M
Chase Headley ? 12.1* ?

*For years 2012-2014 and estimating Headley at 2 WAR in 2014

As you can see, Headley compares favorably to that group of 2013/14 free agents, and they all got multi-year deals near the $14/$15 million mark annually. The teams that signed those players had to take on multiple years of risk and $30-plus million commitments for players generally past their prime (and worse than Headley), but the Padres are worried about shelling out $15 million to Headley on a one-year deal?

Another positive factor if Headley did accept, along with getting a fair market deal on a solid player with a good chance to rebound, is that he’d be able to rebuild his trade value, potentially allowing the Padres to trade him at next year’s deadline for a bigger haul. A healthy Headley with an upper-.700s (or higher) OPS and plus defense might suddenly become a valuable commodity to a pennant contender with a hole at third.

In all likelihood, however, Headley wouldn’t have accepted the QO anyway. While some players may be more likely to accept going forward looking back at what happened with players like Stephen Drew and Kendrys Morales this past offseason, Headley is better than those players and while the QO attachment might stifle some interest in him, he’s still likely in line for a decent payday this offseason.

If he had declined, the Padres would then have picked up an additional draft pick likely somewhere in the 30s. Based on past studies of draft pick value, a player selected in the 31-40 range of the draft produces on average 2 WAR in his first six years of MLB service time. Draft pick value falls off quickly after the first 10 picks or so, so while picking up an extra selection at the end of the first-round is great, it certainly doesn’t guarantee a major league regular.

On the plus side, though, it would have given the Padres an additional scratch-off shot at picking up a star. Since 1990, here are some of the notable players taken with each pick in that 31-40 range:

Pick No. Players
31 Jarrod Washburn
32 Justin Thompson
33 Brad Wilkerson
34 Todd Frazier
35 Johnny Damon, Aaron Rowand
36
37 Adam Jones, Jacque Jones, Troy Glaus
38 Gio Gonzalez, David Wright, Kelly Johnson
39
40 Huston Street, Milton Bradley

That’s 14 star (or borderline star) players out of 250 draft picks, which works out to a 5.6 percent hit rate. Once you consider that a number of those picks — the recent ones — haven’t been given time to develop, it doesn’t look so bad. An additional shot at getting someone like David Wright, or Johnny Damon, or Adam Jones might be under 10 percent, but it’s still a shot worth taking. Even more, giving another high pick to a new GM who is supposed to specialize in drafting and developing youngsters is all the better.

Further, picking up an extra mid-30s draft pick would have given the Padres extra spending flexibility in next year’s draft. Add the would-be compensation from losing Headley to the competitive balance pick the Padres recently received, and suddenly the Padres might have been looking at one of the highest draft budgets of 2015. The 31st pick last year, for instance, was worth $1.7 million. The extra draft pick not only would have given the Padres an extra player, it also would have given them a better chance to shoot for a high upside, high risk tough-to-sign player early on.

Holding onto Headley, whether he accepted the qualifying offer or not, would have been a win-win for San Diego.

Instead, the Padres took what they probably deemed the safer route in dealing Headley to a contender for a couple of fringe players with outside chances of turning into real contributors, finally putting an end to years of trade rumors. In the offseason, the Padres last ditch effort to extend Headley beyond 2014 was reportedly a three-year, $33-39 million deal. It’s hard to believe that after almost 10 years in the organization, the Padres used 300 plate appearances from this season to suddenly sour on Headley to the point where the mere possibility of having to pay him one-year, $15 million forced them to ship him off to New York for pennies on the dollar.

Overreaction to small samples seems to be a somewhat startling organizational trend, however. The Padres were apparently on board with Josh Byrnes running the ship prior to this season, even though they had two-plus years of work to evaluate him as the Padres GM, another five as the Arizona Diamondbacks GM, and nearly 20 years total in professional baseball. When just about every offensive player outside of Seth Smith forgot how to hit, the Padres brass quickly decided enough with Byrnes and canned him mid-season. More recently, after Byrnes’ departure, the Padres extended Seth Smith largely based off a three-month hot streak, rather than dealing him at peak value at the deadline. Hopefully, with a new GM expected to be crowned in the near future, the Padres will return to a more sound decision-making process, leaving their current haphazard, reactionary style as a distant memory.

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