Where Does Cole Hamels Fit Into the Philadelphia Phillies’ Future?

Before the times of Roy Halladay, Cliff Lee, and Roy Oswalt, there used to be an ace in Philadelphia that went by the name of Cole Hamels.

After the 2008 season, World Series MVP trophy and championship ring in tow, Hamels signed a three-year, $20.5 million extension with the Philadelphia Phillies that would keep him in red pinstripes through 2011.

A couple of years and three aces later, Hamels now finds himself set to begin the 2011 season as the fourth best starter on a loaded pitching staff that is expected to catapult the team into an automatic spot in the World Series.

Alright, it’s not that easy. What also won’t be easy will be re-signing Hamels to another new contract sometime soon that will keep him with the Phillies for the foreseeable future.

After the 2008 season, with Hamels set to go to arbitration, the Phillies structured a new contract that worked for both sides. The three-year deal did not touch his final year of arbitration or any of his free agent years. The deal was unique, however, in the sense that it provided Hamels with the biggest AAV (average annual value) ever on a multi-year deal for a pitcher in his first year of arbitration. 

Now the Phillies will have to work something out all over again, or take Hamels to arbitration after next season. It’s likely not something they want to have to do, but it is certainly possible. He can become a free agent after the 2012 season.

General Manager Ruben Amaro, Jr. has locked key pieces in, including Lee, Halladay, Ryan Howard, and Chase Utley, through at least 2013. Besides Hamels, Amaro will have to make crucial decisions on numerous other players.

Jimmy Rollins is slated to be a free agent after next season. Brad Lidge has a hefty club option lined up for 2012, but the Phillies could buy him out after 2011 for just $1.5 million, which seems likely. Ryan Madson, who could be in line to close in 2012, is a free agent after 2011. Raul Ibanez will also become a free agent after 2011, but that won’t be as tough a decision as the others.

There is no question the Phillies will have money to play with, but they’ll have to use it wisely. Regarding the rotation, Halladay is signed through 2013 with a club option for 2014. Lee, with his new contract, will be here through 2015, potentially 2016, if his option vests.

Oswalt will make $16 million in 2011. The Phillies hold a club option for 2012 at the same number, but can buy Oswalt out for $2 million. Right now, it would seem like a relatively safe bet that the Phillies would do such a thing, leaving Hamels as the only truly undecided member of the 2012 rotation.

Hamels will make $9.5 million in 2011, a far cry from any of the numbers Lee, Halladay, or Oswalt will rake in. It’s pretty safe to assume that had Hamels been on the open market this offseason, he could have gotten a deal very similar to Lee’s, maybe for slightly less on the dollar side.

The Phillies’ philosophy since Pat Gillick joined the organization has been to go no longer than three guaranteed years on a contract with a starting pitcher. They have, for the most part, held to that. Lee was a special case that required the Phillies to open up the checkbook for a deal longer than they might have completed in the past. It did show a bit of a change in philosophy, but it was a special occasion.

Could Hamels be another special occasion? While many players have lauded Philadelphia as a great place to play, and Hamels has embraced the area, he’s going to be looking for money. The Phillies can’t expect to be able to go short-term with Hamels.

After a disappointing 2009, Hamels rebounded nicely in 2010. It wasn’t really a surprise. He threw a lot of innings in 2008, and ran into some bad luck in 2009. It was a bad combination for him to succeed. Last year was different, as Hamels posted a 3.06 ERA. The 12-11 record can be discarded; he received some of the worst run support in the league.

The Phillies will have to decide how to fit Hamels in to the future. It’s likely that a five-year contract could be offered. Three probably won’t be enough to keep him here. There is also no way the Phillies will get close to the same AAV that they got on Hamels’ original extension.

A three-year deal for Hamels in today’s market would, conservatively, cost the Phillies somewhere around $50-52 million. If I were Ruben Amaro, I would offer Hamels a new contract sometime next season, and structure it like so:

2012: $15 million

2013: $16.5 million

2014: $17 million

2015: $17.5 million

2016: $18 million

There, of course, would be various add-ons like Cy Young finishes, All-Star appearances, and the like. But that would be the structure, and it would be fair for both sides. It’s a five-year, $84 million deal in total, without bonuses and such. Hamels would be 33 at the end of the deal.

That deal averages out to $16.8 million in AAV, which doesn’t quite put Hamels in the upper-echelon with guys such as C.C. Sabathia, Lee, and Halladay. Something like this might not even be enough to get it done, which is why the Phillies should communicate early and often with Hamels. The Phillies, realistically, should be willing to go up to about $90 million over five years with Hamels.

If talks break down, there is always the option of trading Hamels next off-season, or even in-season, for a package built around youth. That’s something that should be off in the distance, though. The Phillies need Hamels, and Hamels needs the Philllies.

All signs would point to Hamels sticking around for a long time to come. While the super-rotation may only be in action for one season, the true ace of the Phillies’ future is Hamels.

Read more Philadelphia Phillies news on BleacherReport.com