Will James Shields' Sky-High Demands, Wait-It-out Strategy Pay off or Backfire?

In less than three weeks, pitchers and catchers will begin reporting to spring training facilities across Florida and Arizona to prepare for the start of the 2015 Major League Baseball season.

There's at least a chance that James Shields won't be among them.

Shields, one of the top free agents when this offseason started about three months ago now, has yet to find a new team and thus potentially could be without a home when the first teams officially open up shop Feb. 18.

At this stage, with the beginning of baseball hurtling ever faster—heck, the Super Bowl has come and gone—it's pretty evident that Shields' approach this winter hasn't worked. And the biggest reason why appears to be that the right-hander and his representation have overestimated his worth—and not by a small margin, either, as Bob Nightengale of USA Today reports:

Remaining on the open market this long likely was not part of the plan. In fact, there were reports in early January that Shields had an offer worth north of $100 million from a team but that said team was one for whom he didn't want to pitch, according to Ken Rosenthal of Fox Sports.

So Shields could have been signed, sealed and delivered a few weeks ago, readying to report to spring training with his new club. At least, in theory.

In reality, Shields' situation has played out exactly the opposite.

There are two very big problems for Shields right now. One, time is running out on him, and so is the money. There are only so many days—and so many dollars—left now that reporting dates are getting nearer, and most teams already have made their major moves and started planning out their 2015 payrolls and budgets.

On top of that, the team that eventually signs Shields, who rejected the Kansas City Royals' qualifying offer, will lose a draft pick in June. That's not something that's easy to give up at this point, only four months out from the draft, especially if it's a first-round choice.

Don Boomer/Associated Press

And two? There are still alternative arms that could be acquired via trade, from Cole Hamels of the Philadelphia Phillies or perhaps Johnny Cueto of the Cincinnati Reds or even one of the Washington Nationals' studs, Jordan Zimmermann or Stephen Strasburg.

In other words, Shields is the best pitcher available by far in free agency, but he's not necessarily the best pitcher available—period.

Shields clearly missed his chance at leveraging his value while it was at its highest point earlier in the winter, as Buster Olney of ESPN writes:

"

With the benefit of 20-20 hindsight, it’s apparent that James Shields reached the zenith of his negotiation leverage on the night of Dec. 9. That was the night when Jon Lester finalized his decision to go to the Chicago Cubs, and the San Francisco Giants and other teams faced the reality that they needed a Plan B.

Shields was in a good spot in that moment, it seemed, because unlike Cole Hamesl, he wouldn’t require a trade investment of prospects, and unlike Max Scherzer, he wouldn’t require the equivalent of a Defense Department budget to sign. Whatever cards Shields held at that time were probably the best he has seen all winter.

But that leverage is now gone, and Shields is in the worst possible spot of any free agent, when most teams are finished spending for the winter and more readily identify reasons to dismiss an available player. In Shields' case, the loudest concerns are about his age (33), his heavy workloads (eight straight seasons of 203 or more innings pitched), his need for a ballpark that forgives his tendency to surrender fly balls to left-center field; his home games have been in the pitcher-friendly Tropicana Field and Kauffmann Stadium.

"

Now, despite all of that, Shields still is a proven, consistent and very durable starter who fits best as a No. 2 but can pitch at the top of a rotation if needed. He's also capable of being an impact addition, the kind who could turn a good team into a great one or a borderline contender into a no-doubt one.

And being the best—and last—readily available option on the open market can be a good thing, provided there is an actual market. That's where Shields' reps at PSI Sports Management have to come into play to build some leverage and get multiple teams—even if it's only two—invested in the idea of how the righty can help them in 2015 and beyond.

That, however, could be part of the problem. According to Nick Cafardo of The Boston Globe: "One prominent baseball official feels Shields has been miscast and not marketed and/or positioned well by his agent, Page Odle. Shields is a super pitcher, but the notion that he’s a bad postseason pitcher seems to have overwhelmed his total body of work."

And yet there plenty of teams are being mentioned as potential Shields suitors—at a reduced price, of course—including the Miami Marlins, San Diego Padres and Toronto Blue Jays, among others, according to Jon Heyman of CBS Sports.

If Shields' market doesn't advance, though, or if some starter on a contender doesn't blow out an elbow early in spring training, then Shields' tough spot will only get tougher.

While some free agents who have lingered on the market too long in recent years (think: Ervin Santana, Nelson Cruz, Stephen Drew and Kendrys Morales last year) were willing to take a one-year, below-market contract and hit the market again a year later, that wouldn't be such an easy path for Shields.

Not only will Shields once again be extended a qualifying offer if he performs like his usual self, but he'll also be a year older. And the chances that some club is going to give a four- or five-year contract to a pitcher entering his age-34 campaign will be dramatically reduced.

After all, the history of starting pitchers getting big money at age 32 or older isn't exactly promising.

The most recent contract handed out to such a starter was Mark Buehrle's four-year, $58 million pact with the Miami Marlins in December of 2011, as Rosenthal points out.

"Buehrle entered the market with an even greater number of innings pitched than Shields has now, but he also boasted a better adjusted ERA," Rosenthal writes. "Executives cite not only Shields’ age as a negative, but also his backlog of innings, declining strikeout rate and spotty postseason performance."

The way this has played out so far has been rather unexpected given Shields' abilities and placement as a top free agent at the outset of the offseason.

It's also been rather unfortunate for Shields, who will wind up signing somewhere, but almost certainly not for the amount of money he had been hoping initially.

The questions now are: How much less money? And how much more time?

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

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