Moshe Mandel contributed to this post.

At this point four years ago, the Yankees faced a difficult choice. They were among the few potential landing spots for Twins’ ace Johan Santana. The match seemed perfect. The Yankees desperately needed an ace. They had just re-added Andy Pettitte, but they still needed someone to slot in ahead of him and Mike Mussina. Santana was there for the taking — Minnesota had made it clear that he would not be with them to start the season. But the Yankees had other plans.

Why trade prospects and sign Santana to a big money contract, when they’d have to wait just one year for another left-handed ace to hit the free agent market? And so they spurned the Twins and waited for CC Sabathia. That was a risky move for sure, but a calculated one. There was no way that Sabathia was signing an extension before his free agency. The Indians had offered him one, but it wasn’t even close to the offers he’d get after the 2008 season. There was also no chance they’d trade him before the season, because they were just one game away from the World Series in 2007. And so the Yankees waited.

We can look at the current market similarly, but it’s not at all the same. Yes, there are a number of high-end pitchers scheduled to reach free agency following the 2011 season. If this were 2008, and the circumstances were similar to Sabathia’s, the Yankees might be justified in sitting it out this winter, sticking with their internal options, and waiting to nab a starter from the free agent market. But as we saw with John Danks’s extension, this is a different game. There might not be any top-end starters left for the Yanks once the 2011 season ends.

Matt Cain: The Giants have some good and expensive pitching, but chances are they’ll work to hold onto Cain. Recent reports indicate that they’ll try to get something done before spring training.

Zack Greinke: He has the best chance of anyone to reach free agency, but it’s not clear if the Yankees consider him an option in New York. Still, a pitcher with his track record at age 28 could be enticing.

Cole Hamels: The Phillies have spent tons of money building their roster. Why would they hold back when it comes to an ace-level left-hander?

That’s the extent of the high-end pitchers on the market — guys who could firmly step into the No. 2 spot, or even the No. 1 spot, for the Yanks. There are some other decent names on the list, such as Anibal Sanchez and Shaun Marcum, but it’s more difficult to see them atop the rotation. These three best fit as top of the rotation arms. Yet once free agency begins we might see only Greinke on the list of available pitchers.

If the Yankees do desire one of these pitchers, they might have to get creative. That would necessarily involve a trade, though it’s tough to envision any of the three pitchers becoming available in a trade — at least before July. But, since this is the time of year when crappy trade proposals run rampant, perhaps we can find something here. In fact, Moshe and I independently formulated the same framework for a deal that would bring Cole Hamels to New York. So, please indulge us for a moment.

Philadelphia gets: Gio Gonzalez, Austin Romine, another non-top-5 prospect from NYY

Oakland gets: Brett Gardner, Manny Banuelos

Yankees get: Cole Hamels

Our trade proposal sucks. But let’s examine it anyway.

Why it works for Philly: Instead of getting one more year of Hamels and then getting six to seven expensive years of free agency, they get four years of Gonzalez at arbitration prices. They also get a few prospects to help replenish their system. Romine in particular could entice them, because their starter, Carlos Ruiz, is 33 this season. The additional prospect helps replenish their system.

Why it works for Oakland: They get an absolute haul for Gonzalez. In fact, that might be the weakest part of this deal (other than the Phillies actually trading Hamels, of course). They get Gardner for three arbitration years and Banuelos for six. Perhaps the Yanks could sub out Betances here, but it still seems unlikely. I can’t imagine Oakland saying no to this.

Why it works for New York: They get a second ace lefty to complement Sabathia. In fact, Hamels is quite similar to Sabathia in terms of their pre-free agency numbers. Through 2008 Sabathia had a 3.66 ERA and 3.62 FIP, while Hamels has a career 3.39 ERA and 3.63 FIP. There are certain differences among them — Sabathia’s pre-free agency numbers came in a tougher offensive era, and he was in the majors longer — but all told they’re fairly even. With one more season along the lines of his 2010 or 2011 seasons, Hamels will be a perfect comp for Sabathia. They’ll both even hit free agency after their age-28 seasons.

Why Philly won’t do it: Philly might have a lot of money on the books, but there’s little stopping them from extending payroll further. They know the value of making the playoffs, having been there every year since 2007. It helps them sell out every game and will lead to a huge TV rights deal, if they don’t already have one. Additionally, after 2013 they have a lot of money coming off the books, so extending Hamels could cause complications in just one season, 2013. Plus, there’s plenty of allure in retaining a homegrown ace. They would probably rather just extend Hamels.

Why the Yanks won’t do it: They’d essentially be trading their No. 2 prospect, their starting left fielder, and a good catching prospect for one year of an ace. Of course, an extension would have to be part of this deal, but that just gives the Yankees the right to pay Hamels $23 million per season for the next six or seven years. There’s a legitimate chance that they don’t want to get bogged down in that kind of contract. There’s also the matter of Banuelos. Do the Yankees think that he can reach Hamels’s heights? That’s a pretty lofty ceiling, as his career numbers show. If they do think he can reach Hamels levels, how long will it take? Can they put together a rotation between now and then that will keep them in the postseason picture? There are tons of question to ask along with this. And that doesn’t even get into the hole in left field.

To reiterate, this will not happen. I’m certain that the Phillies will sign Hamels long-term. I’m also certain that Brian Cashman will not pay this type of premium for a pitcher just one year away from free agency. If anything, the players involved in this deal illustrate the value of developing pitchers internally. The Phillies have gotten several good to excellent years out of Hamels. If they can swing their final year of cost control for another young lefty, plus prospects, that’s a huge win. Even if Banuelos won’t reach Hamels’ production, even reaching 80 percent of it would probably make him more valuable as a pitcher to the Yankees.

It’s easy to become antsy at this point. The Yankees have some flaws in their rotation, and we’d prefer to see those addressed before the 2012 season begins. But given the asking prices of available pitchers, it just doesn’t seem likely. After all, would you give up all that even for Hamels?

The aftermath of the Phillies signing of Jonathan Papelbon has produced a few predictable responses. Certain folks panned the deal, because they think that relievers, even closers, are fungible and that their volatility does not warrant long, lucrative contracts. Others praised Phillies GM Ruben Amaro for further shoring up his 2012 team and heading for another playoff run. Most relevant to the Yankees, speculation ran rampant about the Phillies’ financial situation. They now have $121.6 million committed to 11 players in 2012, with some big numbers due to Cole Hamels and Hunter Pence through arbitration. Might they be willing to deal Hamels, who will be a free agent next winter?

Yesterday Buster Olney (Insider-req’d) laid out a Hamels trade as one of the Phillies’ three options. The Phillies can hold onto Hamels for one more year and let him enter the 2013 free agent class, they can offer him an enormous extension, or they can trade him now and try to recoup some of his value — perhaps replenishing a farm system that they have somewhat depleted in the last two years while acquiring Cliff Lee, Roy Halladay, Roy Oswalt, and Pence. Yet the trade option seems entirely unlikely, given the current and future states of the Phillies.

The Phillies are, first and foremost, a win-now team. They have won the NL East every year since 2007, and for the last two years they have owned baseball’s best regular season record. In each of the three years following their 2008 World Series Championship they have raised payroll, adding $15 million in 2009, $25 million in 2010, and almost $28 million in 2011. As Matt Gelb of the Philadelphia Inquirer notes, it doesn’t appear that the Phillies will limit themselves when it comes to payroll issues. They sell out every game and led MLB in attendance last season. They pull better local TV ratings than any other team, which could lead to a huge media rights deal, perhaps larger than the one the Rangers currently signed. This all points to a rising payroll, perhaps even approaching pinstriped proportions.

Even if the Phillies realize that they don’t have the payroll to keep Hamels past 2012, trading him isn’t much of an option. A team in win-now mode cannot afford to deal a pitcher of Hamels’ caliber. Olney speculates that they’ll get 90 cents on the dollar if trading him this winter, but even that seems optimistic. Moshe recently wrote about the troubles of dealing for an ace. This applies directly to Hamels, whether or not you consider him a true ace (whatever that means). Look back at recent deals for aces: Johan Santana, Roy Halladay, CC Sabathia, and Cliff Lee. How much are the players traded helping their teams? This matters even more in a Hamels deal, since he’s coming from a contending team. The Phillies need players who can help them win now, and even a package of three helpful players will not equal what Hamels can provide.

It is probably in the Phillies’ best interest, then, to retain Hamels for at least the 2012 season. In this scenario Olney warns that, because first-round free agent compensation could disappear next off-season, “they would run significant risk of watching a homegrown, talented pitcher walk away with almost nothing to show for it (other than their 2008 championship rings.)” That’s always a risk, for any team with an impending free agent. The Phillies, however, are in a position to add a 2012 championship banner, and they’re in a much better position for that with Hamels than without. Another championship could also further boost the team’s financial strength.

If the Phillies do wish to retain Hamels, chances are they’ll approach him this winter with an extension offer in hand. How much would it take? Hamels will be 29 in 2013, which makes him comparable to CC Sabathia in age and ability. From 2001 through 2008 Sabathia produced an ERA-* of 83. In his three years leading into free agency he produced an ERA- of 69, which was second best in the majors to Johan Santana (min. 450 IP). In his career to date Hamels has an ERA- of 80 and in his last two seasons it’s 74. Add in another high-quality season and he’s right at Sabathia’s level. On the open market next winter that could easily fetch him a six- or seven-year deal in the $140 to $160 million range. In buying out his last year of arbitration, perhaps the Phillies could get away with a seven-year deal in the $150 million range, or six years and $140 million at best.

*ERA- is like ERA+, but in reverse. It also creates easier comparison scales between players. That is, you can say that at an 83 ERA-, Sabathia was 17 percent better than average. This is not necessarily true of a 117 ERA+. If you want an esoteric explanation of why, read this article by Patriot.

And yet, it seems as though the Phillies have the payroll for that. They clearly have it this year; Papelbon’s salary merely replaces the departing Brad Lidge’s, so there’s no big change there. With Hamels at $23 million, the Phillies would have $118 million committed to six players in 2013, with Jimmy Rollins as a possible seventh player (likely bringing payroll to near $130 million). If that sounds awful Yankee-like, well, it is. They have $127 million committed to six players in 2013. With another sellout season in 2012, which is all but guaranteed, plus a deep playoff run, the Phillies could easily justify the continuing rise of their payroll into Yankee territory. If that is indeed the case, signing Hamels makes all the sense in the world. (Remember, Roy Halladay’s deal expires after 2013.)

The 2013 free agent market for starting pitchers once appeared a gold mine of talent. Little by little that will dwindle. Jered Weaver is already off the board, and Hamels could be next. That leaves Matt Cain, John Danks, Zack Greinke, and Anibal Sanchez: a good group, for certain, but not the class that we had once envisioned. There still remains the chance that Hamels reaches that point and becomes the most coveted starter on the 2013 market. But given the Phillies position that seems unlikely. They’re going to need Hamels in the future if they’re going to maintain their high payroll and winning winning ways. That means that they’ll almost certainly hang onto Hamels this winter, no matter what a few national writers might speculate.