Who is the next $100 million pitcher in MLB?

Rob Grabowski-USA TODAY Sports

Homer Bailey joined what is becoming an increasingly less selective group, leading us to wonder ... who's next?

With Homer Bailey striking it rich on Wednesday, agreeing to a six year, $105 million contract extension with the Cincinnati Reds, it's clear that $105 million doesn't exactly buy what it used to. The question going forward then, isn't necessarily what a nine-figure contract will buy -- but who?

That the Reds and Bailey were discussing an extension was no great secret, though the total sum was a minor surprise. The consensus then is that this is merely the price of doing business if you want to lock up the non-decline phase of a pitchers career.

In the same vein, we know that Max Scherzer and the Detroit Tigers are in the midst of a contract negotiation that will likely make Bailey's money look like pocket change. Excluding Scherzer, then, we're left to wonder: who is the next $100 million pitcher?

The easiest route to our destination is to look towards the next free agent class, which has become light on pitching with the extensions of Clayton Kershaw, Bailey and our self-imposed exclusion of Scherzer. It leaves us only with the Royals' James Shields and Boston's Jon Lester as possible options.

Shields will be completing his age 32 season as he enters free agency, and while he has clawed his way to borderline "ace" status, his age will likely work against his chances of pulling down nine figures. What was once working for Shields -- his ability to log 220+ innings -- could be turned against him in the negotiation process as teams will question the toll his seven consecutive seasons of 200+ innings (not including playoffs) have taken on him. While he'll likely earn a healthy payday, life is as much about timing as it is anything else, and it seems as though the timing of Shields' free agency leaves him unlikely to satisfy our search.

Lester on the other hand, compares favorably to Bailey in that he's a better pitcher in most every aspect. Again, age will be a factor, as any contract extension for Lester begins with his age 31 season but he's also had a total of one season that checked in below league average (by ERA+) and has eclipsed the 200 inning mark in five of the last six years, falling short by a mere eight innings. While Lester seems unlikely to return to the halcyon days of 2009-10, he's proving to be able to pitch with slightly diminished stuff, and his impressive performance in the playoffs will certainly curry favor with the locals. He's expressed interest in staying with Boston in the form of a hometown discount, but the question is how much of a discount he's willing to take.

If we skip ahead to the free agent class following the 2015 season, we see the likes of David Price, Mat Latos, Jordan Zimmermann and ... wait ... this can't be right. Zack Greinke?

Indeed, Greinke's six year, $147 million contract with the Dodgers included an opt-out clause that is available to him after the 2015 season. By exercising it, he'd be leaving three years and $71 million on the table, which seems risky, though not unthinkable. CC Sabathia exercised his own player option in a similar scenario, re-upping for more money.

The Nationals' Zimmermann seems to walk the line of underrated to overrated and back again. He's only reached the 200 innings plateau once (2013), and is generally only around the league average in strikeout rate, though neither of those facts have stopped him from being a generally better pitcher than Bailey has the last few years. Anticipating some more inflation, and the same pattern of performance, it's not hard to peg Zimmermann as a candidate for a $100+ million contract.

What some are reluctant to call Zimmermann, no one hesitates to call Latos. He might not qualify for the nebulous title of "ace" but he fits solidly in the number two pitcher archetype, at worst. He's shown the ability to log innings, miss bats and amazingly, keep the ball in the bandbox of a park he calls home. Latos will be entering his age 28 season when he reaches free agency, making him a prime candidate for a massive offer if he can continue to stay healthy and productive. Working against him though is Cincinnati's market size and their current long term to commitments to Joey Votto and now Bailey. Indeed, Latos may have to wait til free agency to ink his big deal.

The big name in this grouping of course is Price. Any team looking to sign him as a free agent will be buying his age 30 season (and beyond), which probably works against him slightly, but teams seem to have less and less fear locking up pitchers into their mid-30s. Having a Cy Young Award in his back pocket certainly won't hurt his negotiating position, nor will his big game reputation. Price seems as much of a lock as anyone to receive a big money contract, with the question being when it will happen. It's unlikely to come at the hands of his current team, but any trade could see an extension soon to follow.

While all the above candidates could be seen as deserving of a $100 million contract, and indeed, all may receive one, the premise dictates a venture at who is the first. The easy way out would be to select Lester, and, never one for hard work, that's the route I'll take. The Red Sox and Lester have both expressed interest in getting a deal done, and with Lester amenable to a discount, it seems reasonable to think a deal is reached during the season.

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