With the calendar ready to flip to 2015, two big-name, big-money free agents remain on the market in Max Scherzer and James Shields, both of whom are proven, highly regarded right-handed starting pitchers looking to score massive contracts.

We’ve already covered the potential payday for Scherzer, so it’s time to give Shields the same treatment, especially in light of recent news that he could be looking for something in the range of $110 million over five years, according to Nick Cafardo of The Boston Globe.

The San Francisco Giants, Boston Red Sox and New York Yankees are three teams mentioned as possible suitors for Shields, per Cafardo. Having three big-market franchises drive up the price certainly could help his case.

Let’s start with what we know in the context of this offseason.

Jon Lester, who, along with Scherzer, was arguably the top free agent this year, scored a six-year, $155 million pact with the Chicago Cubs at the winter meetings. Scherzer’s camp, meanwhile, has been more open about his intentions, namely getting north of $200 million, according to Jon Morosi of Fox Sports.

Most would agree that Shields isn’t in the same class as Scherzer and Lester, though, so a deal for $150 million-plus, like the one Lester already signed and the one Scherzer is trying to top, is out of the question.

But many would argue that Shields is a lot better, safer and more consistent than, say, Brandon McCarthy, the injury-prone right-hander who got $48 million over four years from the Los Angeles Dodgers.

Then there’s Ervin Santana, another righty, who picked up $55 million in his four-year contract with the Minnesota Twins.

So Shields’ deal will fall somewhere between $55 million and $155 million, but (no duh) that’s a rather wide gap, to put it mildly.

It might sound surprising initially, but in a way, Shields is something of a rich man’s Santana. After all, both are proven, experienced right-handers over 30 years old with a history of durability and better-than-league-average production but not quite ace-caliber performances.

Both Shields and Santana also have had fluctuations in their production, including multiple seasons in which they were very hittable and homer-prone. Just check out Shields’ 2009 and 2010, and Santana’s 2009 and 2012.

Shields’ reputation carries more weight, and in fact, he has been a better pitcher than Santana, but it’s not crazy to suggest that Shields is closer in value to Santana than he is to Lester and Scherzer.

When put in that context, Shields shouldn’t be a $100 million arm—not when Santana is a $55 million one. Even that price seems a steep one for the Twins to have paid.

In the history of Major League Baseball prior to this offseason, only 25 players had signed contracts worth $100 million or more as free agents. Lester, of course, became the 26th.

Of that very small batch, including Lester, just 14—barely half—were entering their age-30-or-older season, and only eight were pitchers.

Combining those two subsets—that is, free-agent pitchers who inked nine-figure contracts after turning 30—leaves us with (count ’em) three up to this point in time: Kevin Brown, Cliff Lee and Lester.

Here’s where we remind you that Shields is not only a free-agent pitcher, but also one who is heading into his age-33 campaign in 2015.

Lest we forget about Shields’ failures in the playoffs—despite his “Big Game” moniker, he owns a 5.46 ERA in 59.1 innings (11 starts) in his October career—that also should be factored into his price tag.

Ultimately, it’s possible that Shields could net the nine-figure contract he’s seeking, because, hey, inflation also has to factor in, right? But if so, he’ll become only the fourth over-30 starter to get that much as a free agent. Ever.

A more acceptable and justifiable amount for Shields would be something along the lines of the five-year, $82.5 million contracts that both A.J. Burnett and John Lackey signed—the former with the New York Yankees entering his age-32 season in 2009, and the latter with the Boston Red Sox heading into his age-31 season in 2010.

Add in some value for Shields’ consistency and durability by comparison, as well as a few years’ worth of inflation, then subtract for his older age, and Shields might—might—be worth going to for $85 million to $90 million—but over four years instead of five—for a contending team with a rotation need.

That’s still about $22 million in average annual value, which would place Shields just outside the top 10 in that category for starting pitchers.

There’s also plenty of risk in giving a 33-year-old pitcher that much money, even one who has no history of arm troubles and has made at least 31 starts and thrown at least 203 innings every year since 2007, as Shields has.

Remember how those Burnett and Lackey contracts played out?

Shields has been a very good pitcher for a really long time, and he’s going to benefit from being one of only two high-end arms left in free agency. That allows him the opportunity to ask for $110 million.

It doesn’t, however, mean any team has to—or should—pay that much.


Statistics are accurate through the 2014 season and courtesy of MLB.com, Baseball-Reference and FanGraphs unless otherwise noted.

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