Max Scherzer figures to crack the $100-million threshold this offseason. But are big contracts worth the risk for starting pitchers? (Duane Burleson/Getty Images)

There are warning signs along the roads dating back 15 years, but this offseason will be like any other. People will drive on past and step on the gas. Max Scherzer will become the 15th pitcher to sign a $100 million contract – OK, yes, it’ll be more like $200 million – and Jon Lester will join him with a nine-figure deal, too. And the fan bases in two cities will be filled with hope, because the fans aren’t writing the checks with all those zeroes, and seven years of one of the best starting pitchers in baseball – durable, productive, electric — sounds pretty good.

But retrace that highway, littered with the wreckage of the biggest pitching contracts in history, and find one that is an unmitigated success. Those 14 pitchers have been paid or are owed a total exceeding $2 billion, and the best grade we can give on one of those deals might be “incomplete.”

Kevin Brown and Barry Zito. Johan Santana and Mike Hampton (Mike Hampton!). Heck, we know Clayton Kershaw – owner of the richest contract ever granted to a pitcher, $215 million dollars – is the best hurler in the game, and maybe someday his annual average of more than $30 million will seem like a bargain. Maybe.

There is a reason pitchers often don’t get to the point at which Scherzer finds himself – six complete seasons into his major league career having never signed an extension of any kind. The vagaries of Major League Baseball’s compensation system dictate a team can assign a player a salary (normally at or near the league minimum) over his first three seasons of major league service, and then he enters three years in which he is eligible for arbitration. In those seasons, he is paid based on comps in the marketplace, like real estate. What other pitchers in their fourth year of major league service pitched a similar number of innings with a similar ERA, etc., and how much did they make?

But because the pitching motion is inherently unnatural, and because shoulders and elbows routinely give out, pitchers often sign deals that “buy out” some or all of their arbitration years and even a year or two or three of free agency – usually exchanging a little less money for a little more security.

Since signing his new contract, only six qualifying AL pitchers have posted a worse ERA than Justin Verlander. (Paul Beaty/AP Photo)

Madison Bumgarner, the San Francisco lefty and newly minted World Series hero, is a perfect example. The five-year extension he signed with the Giants prior to the 2012 season includes an $11.5 million salary for 2017, what would have been his first year of free agency. It also includes two club options, for 2018 and ’19, at $12 million apiece. So, for $35.5 million, the Giants could have a frontline starter for three years in the prime of his career. If Bumgarner remains healthy, it’ll be the best bargain in baseball. If he misses time with injuries, the Giants haven’t spent a quarter of their payroll on him. And he could still be a free agent at age 30 – Scherzer’s age now – ready to reel in a nine-figure deal. Everybody wins.

Scherzer, drafted by Arizona and traded to Detroit prior to 2010, never signed such an extension (which Lester did once with Boston). Instead, he went “through the system,” avoiding arbitration each year by signing three one-year deals. The last of those, for 2014, paid him $15.25 million. Hardly chump change. He turned down an extension from Detroit last year, reportedly worth $144 million over seven years, to get to this point – free to sign with any of the 30 clubs, an amazing bet not only on his performance but on his health. Scott Boras, his agent, has a history of guiding his players through to free agency – and then commanding historic contracts.

But what of history? The average age of the 14 pitchers who signed $100-million deals was slightly more than 28-1/2 in the first season of those pacts. Only Justin Verlander, Cliff Lee and Brown were older than 30.

How did those work out? Brown, baseball’s first $100-million player, was outstanding his first two seasons with the Dodgers (31-15, 2.80 ERA, 1.030 WHIP), injured his third and fourth, solid again in his fifth – and traded to the Yankees for the final two years of the deal. The Dodgers never appeared in the postseason with Brown on the team.

Lee, 32 when he signed, was brilliant for the first three seasons, 2011-13, posting the National League’s fourth-best ERA (2.80) and second-best WHIP (1.05) while throwing the second-most innings (666-1/3) over that period. But he was limited to 13 starts in 2014 because of an elbow injury, and he won’t throw until sometime this month. What do the Phillies have going forward?

Verlander is one of the most interesting cases. In the four years leading up to his deal, only Felix Hernandez had a better ERA among American League starters (2.81 to 2.95), and only Hernandez threw more innings – by 1/3 of an inning. Verlander struck out the most men and had the best WHIP.

In the two years since: Only six qualifying AL pitchers have a worse ERA than Verlander, who has been paid $40 million for those seasons. Next up: the five remaining years at $28 million per.

“He’s a warrior,” one scout said. “But all those innings add up.”

Related: James Shields, 33 next Opening Day, could also get $100 million from someone. If he did, he’d be the second-oldest pitcher ever to land one, trailing only Brown.

Evaluating the impact of such a workload – not just for next year, but for four years from now — is nearly impossible. Even some deals that must be deemed successful at some level can turn sour. CC Sabathia led the Yankees to a championship in the first season of his seven-year, $161-million deal in New York. That has since been replaced by a five-year contract that extended Sabathia’s time with the Yankees through 2016, and the big left-hander now has chronic knee problems that could hobble him the rest of his career. Pay for a World Series up front, sure. But there’s a real possibility you’ll pay for it for years to come, too.

Not to mention, Sabathia is one of only three pitchers to win a World Series in the midst of a $100-million deal. The others: Matt Cain of the Giants in 2012, and Zito with the Giants in both 2010 and 2012 – the first year of which his performance was so poor he was kept off the postseason roster.

So go back to the debris at the side of the road. Santana, a two-time Cy Young winner with Minnesota, missed two of the final three seasons of his $134.5-million deal with the Mets. The Yankees looked as if they made a brilliant move by signing 25-year-old Masahiro Tanaka from Japan, but that $155 million contract is iffy headed into this offseason given Tanaka’s arm issues in the second half of 2014. Hampton, whose $121-million deal with Colorado in 2001 seems silly now, missed two complete season with elbow injuries. Even deals that could still be a success – Cain, Verlander, Homer Bailey – are burdened by questions about injury and workload.

Cincinnati’s Bailey illustrates another difficulty: Valuing your own pitchers. At 28, he signed a $105-million deal that bought out his last year of arbitration and his first five years of free agency. But 23 starts into the contract, he had surgery to repair a tendon in his forearm. Such developments can explain why, say, the Nationals extending Jordan Zimmermann – whose numbers say he’s a far better pitcher than Bailey – is a difficult deal to pull off. The two sides currently aren’t talking.

This is certainly not to suggest Scherzer won’t get the second-most lucrative deal for a pitcher, and the most for a right-hander – perhaps falling in between Kershaw and Verlander. The game is healthy, with the past decade producing the 10 highest attendances ever, and lucrative local television rights packages keeping the money flowing further.

But if your team signs one of those nine-figure deals, hold your breath. The money is guaranteed. The payback is not.


(Graphic by Todd Lindeman/The Washington Post)

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