It’s almost the end of May and the Philadelphia Phillies sit in last place of the NL East. Their record isn’t horrible, and their offense has been crippled by injuries to Ryan Howard and Chase Utley, but their slow start has caused Ruben Amaro, Jr. to make some surprising comments to the media about the July trading deadline, "We just have to get on track. But if July comes and we’re playing like this, we’ll be sellers." If the Phillies’ struggles continue and they end up actually selling come late-July their star left-hander, Cole Hamels, who will become a free agent after this season, could be a valuable piece to move.

It has been rumored that Hamels’ agent has asked the Phillies for a 7-year contract extension.The claim of that particular rumor is that the Phillies agreed to the annual salary, but not the 7-year length.My best guess for the deal Cole is looking for probably has an AAV of around $20 million, as Roy Halladay and Cliff Lee’s contracts have AAV’s in that range. A 7-year deal may seem preposterous to Philadelphia right now; however, we don’t know what the climate of the baseball world will be like this off-season, as some of baseball’s biggest spenders have had rough starts. If big spending teams don't make the playoffs, some crazy money could end up being thrown around in free agency, making a 7-year contract to a pitcher like Hamels well within the spectrum of possibility.

Signing any player into his mid-30's for over $100 million is a risky move for any baseball organization. Barry Zito's 7-year $126 million contract with San Francisco is enough to make any organization wary of making the same mistake. Zito signed that deal prior to his age-29 season, the same age Hamels will be in 2013. However, Hamels is a much safer bet than Zito was at the time of his contract. Hamels is still in the middle of his age-28 season, but currently in his career he has amassed 1223.2 IP (189 career starts) with 79 ERA-, 84 FIP-, 81 xFIP-, good for a total of 24.8 fWAR. When Zito signed with the Giants he had 1430.1 IP (222 career starts) a 80 ERA-, 95 FIP- for a total of 24.2 fWAR. Since xFIP data became available (2002), Zito's xFIP- makes him look even worse, as his xFIP- from 2002 until he signed with the Giants was 105, 24 points worse than Hamels. The numbers show that Hamels has been a much more effective pitcher than Zito was before signing his massive contract, but is just being better than Zito enough to justify a 7-year contract?

Of course not, in order for a team to give Hamels a 7-year/$140 million deal, they would have to believe that he would at least be a 4-win player for the first half of the deal and a 3-win player at the back-end.

Hamels became a full time starter, in 2007, and since then he's been a 4-win pitcher (based on fWAR) on average, with his best season coming last year (his age-27 season) when he posted a WAR of 4.9. In his contract year, this season, he’s pitching better than ever. His current ERA (2.17) is better than he’s put up in any season and his xFIP (2.89) and SIERA (2.77) show that his very low ERA is pretty legitimate, and will in all likelihood stay below-3. Hamels' 2012 K-rate (9.53) and K/BB ratio (5.08) are both above his career highs, this is due in large part to the second highest swinging strike rate of his career (13%), and the highest among all qualified starters in baseball at the moment.

All signs point to Hamels being in his prime, right now; which is what we would expect from a pitcher during his age-27 to 30 seasons. A contract of seven years in length, would run through Hamels' age-35 season; thus, paying for past-prime decline seasons. In order to be a 3-win player at the back-end of my projected contract, Hamels would have to make adjustments in his approach, as any good, but aging, pitcher must. The main adjustment he'll have to make will deal with the inevitable decrease in his velocity as he ages. As shown in the impressive research of Bill Petti and Jeff Zimmerman, the steepest decline in velocity occurs for pitchers during the ages that Hamels is looking to be signed for. Hamels will need to offset this decrease in velocity with good location and movement. I'm no scout, but I wouldn't be surprised if Hamels is smart enough to make those adjustments and still be an above-average starter in his mid-30's.

Hamels is really good right now, and in my opinion he's going to continue being very good as he crosses the age-30 threshold. But that shouldn't stop the Phillies from moving him.

The Phillies are in last place of the NL East and are the only team currently below .500 in that division. Baseball Prospectus' adjusted standings have the Phillies in third place, which is obviously better than last, but their playoff odds are only 34.3%. A one in three chance of making the playoffs isn't very good at all, and is probably what has caused Amaro to make comments about selling at the deadline.

Even if the Phillies are a playoff contender, or even are a lock to make the playoffs, I still think trading Hamels during this season makes sense for two reasons.

The Phillies offense isn't good enough to win in the playoffs even if they make it. Just making the playoffs is not enough for Philadelphia fans; they expect a World Series or the season was a complete bust. Currently their team wRC+ is 96 and wOBA is .313; which is slightly worse than their offense last season, which wasn't strong enough to get out of the NLDS. A (possible) return of Utley and Howard, might be enough to put Philadelphia into the playoffs, but not enough to make them a championship team, because those players are mere shells of their former selves at this point.

Keeping Hamels in Philadelphia instead of trading him does not make sense financially, which is even more important than whether or not the Phillies make the playoffs. The 2008 World Series championship turned the Phillies from above-average spenders to a super-power among MLB payrolls. The Phillies' average payroll for the four seasons prior to 2008 ('04-07) was $91,387,845, while their average payroll in the four seasons since that championship is over $60 million higher ($155,021,356). Phillies currently have the third highest payroll in baseball, just over $172 million, which is the highest payroll in the history of their organization. In 2008, they had the 12th-highest payroll in baseball (just over $100 million). In each season since, they've never had a payroll lower than fourth-highest. This massive increase in spending has left Philadelphia with some serious payroll obligations for the next five seasons.

Below I've posted a chart with with the payroll obligations for the Phillies from 2013-17, based on four different scenarios:

Phillies Payroll Obligations Year No Options/No Hamels Options/No Hamels No Options/Hamels Options/Hamels 2013 $112.636 million $127.136 million $132.636 million $147.136 million 2014 $74 million $94 million $94 million $114 million 2015 $68 million $74 million $88 million $94 million 2016 $37.5 million $52.5 million $57.5 million $72.5 million 2017 $10 million $23 million $30 million $43 million

The first two columns show how much money the Phillies already owe to players if Hamels were to sign with another team in 2013, with the first showing their obligations if they do not exercise any club options, and the second has their obligations if all of those options were exercised. The players with options are: Ty Wigginton (2013), Carlos Ruiz (2013), Jose Contreras (2013), Halladay (2014), Jimmy Rollins (2015), Lee (2016), Jonathon Papelbon (2016), and Howard (2017). I assume Philadelphia will exercise a good majority of these options, and in the cases of Rollins, Lee, Papelbon, Halladay the options become automatic if those players accumulate a certain amount of playing time, so Philly won't really have a choice.

The final two columns reflect their obligations if Hamels is signed to a 7-year $140 million contract, the third column again with no options being exercised and the fourth with all eight becoming effective. The crazy aspect of these numbers is that the obligations are extremely high, yet do not include Hunter Pence's 2013 final year of arbitration, or any arbitration years of Phillies' youngsters, such as Antonio Bastardo, Kyle Kendrick, John Mayberry, Jr., and Vance Worley. Also, the numbers on the table show payrolls before any new free agent signings, or re-signings of current players when they become free agents again over these five seasons.

The Phillies have a ridiculous amount of money committed to a small numbers of players for the next couple of seasons. An extension or re-signing of Hamels could push their payroll to even higher levels than their franchise record payrolls of the past four seasons. Keeping Hamels around for five to seven more seasons would seriously handcuff their front office, in terms of going after free agent talent, unless they would be willing to cross the $200 million dollar payroll plateau and reach spending heights that only the Yankees understand.

Matt Swartz wrote a brilliant article for Fangraphs, about how much of Major League team's WAR comes in the form of NM WAR (non-market WAR), or from cost-effective players who have yet to become eligible for free agency. Swartz discusses how important the combination of a high payroll and a good farm system is to being a playoff team. This seems pretty obvious, but the Phillies should understand this as much if not more than any other team. Their 2008 World Series team had a fairly high payroll, but was flushed with home grown talent.

Four of the top six hitters (Howard, Utley, Rollins, and Pat Burrell) on that team, in terms of WAR, were drafted by the Phillies, and the other two players, Jayson Werth and Shane Victorino were acquired before they had compiled enough Major League service to be eligible for free agency. Hamels was their most valuable pitcher, by far, that season, and he also was a product of Phildelphia's farm system, who made just $500k that season.

Yet, the Phillies' current organization does not seem to understand this winning formula, as their farm system is well below-average. Their system ranks 20th on Fangraphs, 24th according to minorleagueball.com, and probably the most respected name in prospects, Baseball America, has them ranked 27th best in baseball. The Phillies want to reach their fans' lofty expectations, and in order to do that I think it's time to start reloading that system, and Hamels is the trade candidate who gives them the best opportunity to help begin that process.

In my opinion, the 2010 trade of Lee from the Seattle Mariners to the Texas Rangers is a solid comp to the current situation with Philadelphia. Lee's Mariners were expected to compete for the title in 2010, but were underwhelming (to say the least) that season. Lee also was becoming a free agent after the 2010 season, and there was a good chance that Seattle and Texas would not sign him, but were still able to workout a trade. That off-season Lee would sign a six-year contract, with Philadelphia, worth either $132.5 or $147.5 million, depending on whether or not Lee's option for 2016 is bought out or exercised.

This sounds fairly similar to what is going on with the 2012 Phillies and Hamels. While Lee was becoming a free agent at age 32, three years older than Cole would be when (if) he hits free agency, their similarities are closer than you'd expect. Lee had1300.1 career MLB IP when he was traded, and Cole projects to have about 1270 IP at this seaon's deadline. So despite the three year difference in age, they had similar major league "mileage" on their arms. In July of 2010, Lee he had a career WAR of 26.9, at the trade deadline this season Cole should have about a career WAR around 26, as well. Hamels may even be a better than Lee was at that time, as his career ERA-, FIP-, and xFIP- are better than Lee's before he was traded in 2010.

In that deal, Seattle sent Lee and Mark Lowe for Justin Smoak, Blake Beavan, Josh Lueke, and Matt Lawson. The names of those then-Texas prospects may not jump out at you, but at the time Smoak was the centerpiece of that trade. Before 2010, Kevin Goldstein ranked Smoak as a five-star prospect, and he was baseball's 13th-best prospect, according to Baseball America, ahead of names like Madison Bumgarner, Starlin Castro, Jeremy Hellickson, Aroldis Chapman, and many more. Smoak hasn't turned into the great player he was expected to be (a career 94 OPS+ at 1B isn't going to cut it in the majors), but he's only 25 and still has time to mature into a solid ballplayer.

Beavan was the Rangers' 16th best prospect at the time and has posted a 4.60 SIERA and 4.57 xFIP in 23 career MLB starts for Seattle, and he's only 23. Lawson is now out of baseball, while Lueke was flipped for catcher John Jaso. The key to this trade was not only that Smoak was supposed to be the future franchise 1B for Seattle (which he still could be), but mainly because the Mariners received young cost-effective talent for a pitcher that they could not afford in free agency, and they had no (real) use for during the second half.

Philadelphia is probably not a true contender and trying to resign Hamels does not make financial sense, thus the Phillies' organization would be smart to make a similar deal. It's been rumored that the Toronto Blue Jays have inquired about Hamels. They're looking for starting pitching help, they've asked about Zack Greinke and Matt Garza as well, to help compliment Brandon Morrow and Ricky Romero as they attempt to make the playoffs for the first time since they beat the Phillies in the '93 World Series. Toronto has a better than usual chance at making the playoffs, with the Yankees and Red Sox both looking weaker and the new wild card system. Hamels could give them a serious boost, and the Jays have the prospect depth to make a move similar to the Lee deal happen.

Toronto has a loaded system, ranking 2nd, 1st and 5th at Fangraphs, MIB.com, and Baseball America, respectively. The Phillies' organization seriously lacks hitting prospects, and Toronto's top two prospects are C Travis d’Arnaud and OF Anthony Gose. D'Arnaud and Gose are both former first/second round picks of Philadelphia that were traded in packages for Halladay and Roy Oswalt, respectively. With Ruiz and Victorino set to become free agents in either 2012 or '13 a move to bring one these top prospects back in a package of other low-cost youngsters could be the first major step for Phillies to rebuild a bad farm system, and get back on track for World Series contention.

My final point is about the uncertainty surrounding this situation. Philadelphia doesn't seem to be comfortable giving Hamels a 7-year contract, which will probably lead to Hamels hitting the open market. And if he does hit the open market and Philadelphia still wants to bring him back, no matter how much it could hurt their financial future, there's a chance that they still won't sign him. Two examples of this I could easily see happening are the Red Sox organization being desperate enough to give Hamels seven years, or he signs a six-year deal with a team who offered more money than Philadelphia.

Then Philadelphia would be stuck with a bad farm system, that has three or four less players than it should have, one less ace, a huge payroll, and what would they have to show for it?

Only one meaningless half-season from Hamels that did not result in a World Series trophy.

All Statistics from Fangraphs. All Contractual Information from Baseball Prospectus' Compensation tables and Cot's Contracts.