Will Cole Hamels Stay or Will He Go?

If the Phillies let him go, remember the Jayson Werth lesson.

Amid this season of unhappiness with the Phillies, one question has been hanging over everything: What of Cole Hamels? The 2008 World Series MVP is the best homegrown pitcher developed by the Phillies in decades and the primary pitching constant in the team’s recent run of success. The 29-year-old Hamels is in the final year of his contract and, unless he agrees to an extension before the end of the season, is eligible for free agency.

Despite minor league years that were riddled with injuries, Hamels has been consistently healthy for his entire major league career. And he’s having one of his best seasons this year. If the second half of his career is anywhere near the level of the first, Hamels is looking at a pretty healthy case for the Baseball Hall of Fame.

While Hamels has come in for some criticism over the years due to his pretty-boy appearance, California heritage and attitude, and not really being a “Philly guy,” most fans—other than this guy—realize by now that he’s a special player who’s deserving of respect. Who cares if he has manicured fingers, if there’s a World Series ring on one of them?

Then there was the interview Hamels sat for this week with the 10-year-old “Awesome Emma” of the Phillies blog Zoo With Roy, which is unquestionably the most media-savvy moment of the pitcher’s career in Philly.

So why haven’t the Phillies locked up Hamels yet? It’s not anything as simple as “they don’t want him” or “they don’t appreciate him” or “they’re too cheap.” No one knows what’s going on with the negotiations, or if there are any. But I think I have a pretty good idea of the dynamic here.

Hamels knows that, if he reaches free agency after the season, he will be the best free agent pitcher available. That means he’ll be subject to a massive bidding war for his services. And this won’t be like Albert Pujols last year, in which some teams didn’t participate in the bidding because they already have a first baseman. There’s always a huge market for an ace pitcher, meaning the Phils will have competition from the Yankees, Red Sox, Dodgers, Angels, Rangers and every other big-spending team in baseball.

That means Hamels will be in a position to demand a whole lot of money and years—probably six or seven years, and a total contract worth considerably north of $100 million. The biggest contract ever given to a pitcher was the Yankees’ seven-year, $161 million deal for C.C. Sabathia in 2008; Hamels will absolutely be in position to command something approaching that. After all, the Giants’ Matt Cain got six years and $127.5 million in the offseason in order to forgo free agency, while C.J. Wilson signed a free agent deal with the Angels for five years and $77.5 million. Hamels is a better pitcher than Cain and Wilson.

Therefore, if the Phils want to re-sign Hamels before the season is over, they’ll need to offer him enough money to agree to not enter that bidding war. And every time he mows down an opposing team, especially with Roy Halladay injured and Cliff Lee still winless, that number’s going to get even higher.

If the Phils re-sign Hamels, they’ll be paying three different starting pitchers—Halladay, Lee and Hamels—more than $20 million per year each, something that’s unprecedented in baseball history. And they’ll be doing it for awhile: Halladay will get exactly $20 million in both ’13 and ’14 (assuming his option is picked up for the latter year), while Lee will earn $25 million each in 2013, ’14 and ’15, with a club option for a staggering $27.5 million in ’16. And yes, that’s after Lee took less money to come back to Philadelphia.

Add to that six or seven years of Hamels making something like Lee’s salary, and that’s a lot of money to commit to the rotation. Sure, it’s great to have elite starting pitching, but imagine how screwed the Phils will be if one or two of them gets injured for any extended period of time. One of the first commandments of baseball roster construction, after all, is that Pitchers Get Hurt. There’s a reason the Phils used to shun contracts for pitchers that went beyond three years, at least before they broke that rule for Lee and again for Jonathan Papelbon.

The attitude of the average fan is “give him whatever he wants,” although “give him whatever he wants” is seldom a wise negotiating strategy. Should the Phils have addressed this situation years ago, perhaps locking up Hamels for seven years instead of Ryan Howard? With hindsight being 20/20, they certainly should have.

It’s hard to imagine the Philadelphia Phillies without Cole Hamels, and I’d rather not. But we must be prepared for such a thing to occur—and if he signs with another team for seven years and has a bad injury in year two, the Phils might be glad they let him go. That’s what happened, after all, with Jayson Werth.