Last winter, Ervin Santana hit some mitigated imitation of free agency, coming off a terrific season with the Kansas City Royals. He’d thrown 211 innings and posted a 3.24 ERA. At 30 years old, he’d posted his best strikeout-to-walk ratio—had really had his best season overall—since his All-Star campaign of 2008. Yet, when the Royals hung a qualifying offer around his neck and sent him out into the marketplace, would-be suitors quailed at the sight. Santana struggled to find a taker into Spring Training, finally latching on with the Atlanta Braves for exactly the price of that offer—one year, $14 million.

That short-term deal has put him right back in the same position this fall. The Braves saddled him with the same ankle weights, the same weighted vest, and although Santana is one year further removed from his stinker of a season in 2012, he also has to turn down a bit more money if he wants to retry free agency this winter. Atlanta had to offer him $15.3 million in order to attach a draft pick to him and wreck his free-agent value this time around.

Should Santana, who joins Nelson Cruz to form the first duo of repeat offer earners, accept that offer this time, and save himself a long winter of trying to get back to the same deal?

In short, the answer depends on whether you think baseball executives learn from the mistakes of their peers and counterparts.

Ervin Santana is at precisely the point in his career Edwin Jackson was at two years ago today.

Ervin Santana, 2012-14, vs. Edwin Jackson, 2010-12

Starts Innings Batters Faced ERA FIP Strikeouts Walks Home Runs
Santana 93 585 2440 4.06 4.27 473 175 81
Jackson 94 598.2 2553 4.10 3.75 497 198 60

Thank God and Sean Forman for Baseball-Reference.com.

As important as those stats, the two pitchers pitch very similarly. Both throw fastballs that sit comfortably in the low-to-mid-90s, and have wipeout sliders. Check out another snapshot comparison:

Ervin Santana, 2012-14, vs. Edwin Jackson, 2010-12

Slider as Percentage of Total Pitches, RHB Whiffs Per Swing on Slider, RHB Slider as Percentage of Total Pitches, LHB Whiffs Per Swing on Slider, LHB
Santana 43.10 % 41.20 % 29.46 % 40.06 %
Jackson 41.10 % 41.77 % 21.46 % 39.01 %

This stuff courtesy of brooksbaseball.net.

Each guy tries to get ahead with heat, and then entice opposing batters to chase runaway sliders. Neither is all that good at, given the pure nastiness of the slider, and so neither racks up quite the strikeout total for which one might hope. Neither is very good against opposite-handed batters, because that slider is easier to ignore when it can be picked up a shade earlier.

Of course, I’m talking as though the Jackson depicted here is the current version, and that’s simply not true. Edwin Jackson signed a four-year, $52-million deal two years ago. Over the first half thereof, he’s posted a 5.58 ERA and virtually washed out of the league. His strikeout rate has fallen sharply. His walk rate has risen to meet it. He’s been terrible, not really because his stuff evaporated, but for a hundred small reasons, from opponents getting a better and better feel for his stuff to poor command to clear physical decline.

Santana is not Jackson, not quite. He has shown more strikeout upside. In fact, Santana set his career-high in strikeout rate in 2014, and the slider, especially, was nastier than ever. Still, he’s always had home-run problems, and the limitations of his repertoire ensure that left-handers will always hit him. If Santana suffers anything like Jackson’s backslide (to be fair, not something most people saw coming, and perhaps unlikely to repeat itself), he could become a liability.

Even if Santana didn’t have warning signs attached, though, he would belong to a profile teams must surely be coming to disdain. In addition to Jackson, Ubaldo Jimenez, Ricky Nolasco and Matt Garza have signed contracts right in the same range—four seasons, roughly $50 million. None of them have panned out. It’s becoming clear that the segment of the market where Santana sits is a muddle where hurlers get almost invariably overpaid.

This really comes down to what Santana wants. He now has the chance to make $15.3 million for 2015, and maybe a strong performance next year could catapult him up into the next tier of arms, where teams spend more comfortably and the track records support that choice. If he prefers the security of a medium- to long-term home, though, Santana will need to prepare to sign a deal falling somewhere on the spectrum from Phil Hughes (three years, $24 million) to Kyle Lohse (three years, $33 million) to Jason Vargas (four years, but just $32 million). If it’s me, I take the big bucks and bet on myself one more time.

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