James Shields could receive five-year deal in free agency

Major League headlines have been swirling around the Kansas City Royals of late. With the team’s 6-4 win over the Orioles today, the Royals have advanced their improbable playoff run even further as the underdogs, appearing in their first postseason since 1985, take a 2-0 lead in the ALCS.

While inspiring for baseball, however, that Royals’ run doesn’t mean anything for the Red Sox. Still, the Red Sox have every reason to be watching the Royals with great care and that’s because Kansas City is the current home of James Shields, perhaps the top free agent target for the Red Sox this offseason.

Chances of Shields coming to Boston may have taken a small hit today though, as many executives throughout Major League Baseball have predicted that Shields will receive a five-year contract this winter. For a pitcher of Shields’s caliber, that wouldn’t normally be a huge issue, but taking age into account, that fifth year could very well determine whether or not the Red Sox heavily pursue him this offseason.

Since the Ben Cherington era has begun in Boston, the Red Sox have been very frugal regarding free agent spending. While they’ve signed a fair number of free agents to reasonable contracts– including Mike Napoli (twice), Shane Victorino, Ryan Dempster, and Stephen Drew— the Cherington regime is yet to sign any players to big time contracts. With Shields in line for four to five years, though, he could very well be the first of an era for a Red Sox team in dire need of strong starting pitchers.

Shields, who posted a 3.21 ERA this season in his second campaign in Kansas City, would fit in nicely at the top of the Red Sox rotation. However, considering Cherington’s history regarding free agent deals, there would have to be some compromise in order. In the past, he has shown a willingness to sign players to contracts with fewer years but higher average annual value and that’s likely a route that the Red Sox could pursue with Shields.

It’s unlikely that the Red Sox could push the length of that contract down to three years, but four is quite reasonable. If the Red Sox were to offer Shields a contract in the range of 4 years/$70-80M, that could be enough to dissuade him from signing a longer, but less-expensive deal with another team. However, if Shields and company are unwilling to budge on a five-year deal, then the Red Sox would be best-suited to look elsewhere for an ace this offseason.