Hey, um, not sure how many of you out there are aware, but the Phillies are on the verge of acquiring Roy Halladay (SI.com is reporting that Halladay has agreed to a three-year, $60 million extension with two vesting options that could keep him in Philadelphia through 2015). OK, OK - I admit. We're a little late to the party here at High Cheese. In fact, what was supposed to be my last post before shipping out on vacation instead turned out to be one of the most irrelevant slices of cyberspace since somebody registered FireUrbanMeyer.com back in 2004. Paul Hagen has the details on the deal-in-progress in today's paper. But plenty of questions remain unanswered, first and foremost being: What in the world is Ruben Amaro Jr. thinking?

If this trade ends up going down - and right now it sounds like there is no turning back - RAJ will have officially attached his legacy as a major league general manager to the right arm of Mr. Halladay. By the time Doc's reported three-year contract extension expires in 2013, RAJ will likely either have a job as a general manager for as long as he wants one, or will be looking to pursue other endeavors. Sound dramatic? Well, this is a dramatic deal. If Halladay proves to be worth the price, the Phillies will likely have a spectacular 1-2 combination at the top of their rotation for the next three seasons (Cole Hamels will be a free agent after 2012). If he falters, the Phillies not only will have sacrificed several top prospects, but will be saddled with a huge salary burden.

The latest incarnation of the deal appears to have top-pitching prospect Kyle Drabek, highly-touted outfield prospect Michael Taylor, and top catching prospect Travis D'Arnaud heading out of town. In their place, the Phillies would receive Mariners pitching prospect Phillippe Aumont, outfield prospect Tyson Gilles, and right-handed pitching prospect Juan Ramirez.

That's a lot to digest. But we'll try to be your enzymes.

I. The Money

This is the most significant part of this deal. Because if Halladay ends up being worth the money for which he signs, then any debate over the prospects that have changed hands will be rendered moot. Because if Halladay earns his $20+ million per season through 2012 (and, if there are options, perhaps beyond), then the Phillies will have themselves one of the Top 3 starting pitchers in the game for the next four years. They will have themselves an absolute horse, one who has thrown at least 220 innings in each of last four seasons while posting an ERA of under 3.75 in the most challenging division in baseball. They will have a guy who has thrown 25 complete games over the last three seasons, a guy who is 4-2 with a 2.79 ERA in six career starts on three days rest, a guy who has appeared 26 times as a reliever, a guy who is 18-6 with a 2.84 ERA in 37 career appearances against the Yankees.

And, most importantly, they will have him during their much-discussed "window of opportunity," giving him two full seasons with Ryan Howard, Chase Utley, Raul Ibanez, Shane Victorino, Carlos Ruiz, Placido Polanco, Cole Hamels, Brad Lidge, Ryan Madson and, provided the Phillies exercise his option after 2010, Jimmy Rollins.

Couldn't the Phillies have held on to Cliff Lee and then atempted to sign Halladay after the season as a free agent, saving themselves Drabek and Taylor?

Probably not. Because all indications were that Toronto was going to trade Halladay. And whoever landed him was likely going to sign him to a contract extension, which would have removed him from the market.

Why not just sign Cliff Lee to a contract extension?

I'm sure the Phillies asked themselves the same thing. Which is why they met with Lee's agent at the winter meetings. But Lee's camp has sent plenty of public signals that suggested they were looking for a monster deal. And who would you rather pay $20 million a year to? Halladay is 15 months older than Lee, but he also has 11 full big league seasons under his belt and has posted an ERA of under 3.75 in eight of his last nine. Lee has been one of the top pitchers in the game for the last two years. But he has a long way to go before he proves himself to be in a class with Halladay. Keep in mind, Lee allowed six or more earned runs in six or fewer innings in three of his 12 starts with the Phillies. Halladay has had one such start in the last two seasons, and just five in his last five seasons.

How risky is paying monster cash to a pitcher through his 36th birthday?

Glad you asked. . .

II. Halladay's staying power

Halladay will turn 33 in May. A three-year extension would bring him through his 36th birthday. Now, attempting to project the future health of players is an impossible task. According to Baseball-Reference.com, one of the most "similar" pitchers to Halladay at this point in his career was Bret Saberhagen, the former Royals ace. Saberhagen was dominant for most of his first 11 seasons in the big leagues. But from that point on, he was a shadow of himself.

Here is how Halladay and Saberhagen compare through their first 11 full seasons in the majors:

Bret Saberhagen
Age: 30
Appearances: 312
Innings: 2,074.2
CG: 73
ERA: 3.19
ERA+: 128
Avg/9: 6.1 SO, 1.7 BB, 8.4 H, 0.7 HR
Last 3 seasons of this window: 60 G, 58 GS, 414.1 IP, 9 CG, 3.11 ERA, 1.064 WHIP

Roy Halladay
Age: 32
Appearances: 313
Innings: 2,046.2
CG: 49
ERA: 3.43
ERA+: 133
Avg/9: 6.6 SO, 2.0 BB, 8.8 H, 0.8 HR
Last 3 seasons: 97 G, 96 GS, 710.1 IP, 25 CG, 3.08 ERA, 1.137 WHIP

Pretty similar, right? Well, Saberhagen went on to start more than 25 games just once more in his career. He missed all of one season and most of another with an injury. In short, he wasn't worth a monster three-year extension. But Saberhagen had also shown signs of wear and tear in the final years before the drop-off. As I've noted above, he appeared in just 60 games in the last three years of this window. Halladay, meanwhile, has started at least 31 games in each of the last four seasons.

Halladay has an extensive injury history, but very little of it has to do with his arm. Since 2004, when he went to the disabled list twice with shoulder fatigue, Halladay has missed time due to a pulled groin, an appendectomy, and a broken leg that occurred when Kevin Mench hit him with a line drive. But aside from that 2004 season, which Halladay said was caused by training too hard in the offseason, he has had no arm problems.

Halladay compares a lot more favorably with other pitchers who finished their 32nd year of life as some of the most dominant in the game. While 32 might sound old, consider: Roger Clemens turned 32 in his second-to-last year with the Red Sox. Curt Schilling turned 32 when he was still a member of the Phillies. Schilling, Clemens, Greg Maddux, Randy Johnson and Kevin Brown were just as dominant or more dominant between the ages of 33-36 as they were between 28-32. Exceptions? Jason Schmidt, Pedro Martinez and Bartolo Colon. But Schmidt didn't have the track record that Halladay has. And Martinez's slight build may have contributed to his breakdown. Halladay is 6-foot-5, 225 pounds.

Here is how they stack up:

Roy Halladay
Years: 2005-09
Ages: 28-32
Workload: 148 G, 147 GS, 1,072 IP
CG: 34
ERA: 3.01
ERA+: 146
Avg/9: 6.7 SO, 1.5 BB, 8.5 H, 0.7 HR

Greg Maddux Before:
Years: 1994-1998
Ages: 28-32
Workload: 155 G, 155 GS, 1,140 IP
CG: 39
ERA: 2.10
Avg/9: 7.0 SO, 1.2 BB, 7.3 H, 0.4 HR

Greg Maddux After:
Years: 1999-2002
Ages: 33-36
Workload: 136 G, 136 GS, 901 IP
CG: 13
ERA: 3.07
Avg/9: 6.2 SO, 1.5 BB, 9.0 H, 0.7 HR

Jason Schmidt Before:
Years: 2002-06
Ages: 29-33
Workload: 151 G, 151 GS, 1,003.1 IP
CG: 14
ERA: 3.35
ERA+: 127
Avg/9: 9.0 SO, 3.2 BB, 7.3 H, 0.8 HR

Jason Schmidt After:
Years: 2007-09
Ages: 34-36
Workload: 10 G, 10 GS, 43.1 IP
CG: 0
ERA: 6.02
ERA+: 70
Avg/9: 6.2 SO, 5.4 BB, 10.0 H, 1.0 HR

Randy Johnson Before:
Years: 1992-96
Ages: 29-32
Workload: 133 G, 126 GS, 913.1 IP
CG: 31
ERA: 3.20
ERA+: 141
Avg/9: 11.2 SO, 4.0 BB, 6.7 H, 0.7 HR

Randy Johnson After:
Years: 1997-2000
Ages: 33-36
Workload: 134 G, 133 GS, 977.2 IP
CG: 35
ERA: 2.68
ERA+: 171
Avg/9: 12.3 SO, 2.8 BB, 7.0 H, 0.9 HR

Curt Schilling Before:
Years: 1995-99
Ages: 28-32
Workload: 137 G, 137 GS, 1,002.2 IP
CG: 39
ERA: 3.26
ERA+: 134
Avg/9: 9.6 SO, 2.1 BB, 7.6 H, 0.9 HR/9

Curt Schilling After:
Years: 2000-03
Ages: 33-36
Workload: 124 G, 123 GS, 894.1 IP
CG: 22
ERA: 3.24
ERA+: 144
Avg/9: 9.8 SO, 1.5 BB, 8.1 H, 1.1 HR

Kevin Brown Before:
Years: 1993-97
Ages: 28-32
Workload: 151 G, 150 GS, 1,045.2 IP
CG: 29
ERA: 3.21
ERA+: 135
Avg/9: 6.4 SO, 2.3 BB, 8.6 H, 0.5 HR

Kevin Brown After:
Years: 1998-2001
Ages: 33-36
Workload: 124 G, 122 GS, 855 IP
CG: 18
ERA: 2.65
ERA+: 156
Avg/9: 8.4 SO, 2.0 BB, 7.5 H, 0.6 HR

Mike Mussina Before:
Years: 1997-2001
Ages: 28-32
Workload: 161 G, 161 GS, 1,100.2 IP
CG: 22
ERA: 3.43
ERA+: 133
Avg/9: 8.1 SO, 1.9 BB, 8.4 H, 0.9 HR

Mike Mussina After:
Years: 2002-05
Ages: 33-36
Workload: 121 G, 121 GS, 774.2 IP
CG: 7
ERA: 4.07
ERA+: 108
Avg/9: 7.6 SO, 2.0 BB, 9.0 H, 1.1 HR

Roger Clemens Before:
Years: 1991-95
Ages: 28-32
Workload: 143 G, 143 GS, 1,020.1 IP
CG: 29
ERA: 3.17
ERA+: 144
Avg/9: 8.0 SO, 2.9 BB, 7.6 H, 0.6 HR

Roger Clemens After:
Years: 1996-99
Ages: 33-36
Workload: 131 G, 131 GS, 929.0 IP
CG: 21
ERA: 3.13
ERA+: 151
Avg/9: 9.5 SO, 3.4 BB, 7.5 H, 0.6 HR

Bartolo Colon Before:
Years: 2001-05
Ages: 28-32
Workload: 168 G, 168 GS, 1,128.2 IP
CG: 20
ERA: 3.85
ERA+: 115
Avg/9: 6.7 SO, 2.7 BB, 8.7 H, 1.1 HR

Bartolo Colon After:
Years: 2006-09
Ages: 33-36
Workload: 48 G, 37 GS, 257 IP
CG: 1
ERA: 5.18
ERA+: 88
Avg/9: 6.0 SO, 2.5 BB, 11.1 H, 1.5 HR

Pedro Martinez Before:
Years: 2000-04
Ages: 28-32
Workload: 139 G, 139 GS, 936.2 IP
CG: 14
ERA: 2.53
ERA+: 189
Avg/9: 10.8 SO, 2.0 BB, 6.7 H/9, 0.7 HR/9

Pedro Martinez After:
Years: 2005-08
Ages: 33-36
Workload: 79 G, 79 GS, 486.2 IP
CG: 4
ERA: 3.88
ERA+: 108
Avg/9: 8.6 SO, 2.5 BB, 7.9 H, 1.1 HR

III. So, is he worth it?

From a prospect perspective - and we'll get more into this once the deal is official - here is what the Phillies will likely have given up and received between last year's trade for Lee and this year's trade for Halladay:

Given Up:
RHP Kyle Drabek
RHP Jason Knapp
OF  Michael Taylor
C   Travis D'Arnaud
RHP Carlos Carrasco
C   Lou Marson
IF  Jason Donald

Received (edited to include Ben Francisco):
RHP Roy Halladay (Plus a half year of Cliff Lee and the chance to re-sign Halladay)
RHP Phillippe Aumont
OF Tyson Gillies
RHP Juan Ramirez
OF Ben Francisco

On paper, the price-tag looks overwhelming for the Phillies. They parted with their top three starting pitching prospects, their top two catching prospects, their second-best position prospect in Taylor and their most major-league ready infield prospect in Jason Donald. Two of those players - Drabek and Taylor - were ranked among the Top 25 prospects in all of baseball by Baseball America in July. One of them - Jason Knapp - was ranked in the Top 50. Three more - Carrasco, Marson and Donald - were ranked in the Top 100 by BA at the start of the season. None of the prospects the Phillies are reported to receive from the Mariners were ranked in the Top 50 by BA in July. Only one - Aumont - was ranked in the Top 100 at the beginning of the season.

Although prospect rankings do provide some perspective, they are not the end-all, be-all. The Phillies, for example, had soured on Carrasco, and there were some in the organization who felt Donald would never be more than a utility player. There were plenty of questions about Marson's defense. And within the Phillies organization, Taylor is viewed as a distant second to Brown when it comes to upside.

But there are some in the organization who are very high on Taylor, and a lot of the same things that are being said about him right now were said about Ryan Howard when he was coming up. And we all know how that turned out. Knapp and Drabek both have injury histories. But both also have huge ceilings. D'Arnaud, likewise, has immense potential. But catcher might be the most difficult position to project at the lower levels of the minors.

The experts say that neither Aumont nor Gillies are viewed as better prospects than Drabek or Taylor. Aumont is, at the moment, a right-handed reliever who saved 12 games and posted a 3.24 ERA while striking out 9.4 batters per nine innings at High Class A High Desert last season at the age of 20. Gillies, a left-handed bat, he hit .341/.430/.486 at high-Class A High Desert with nine home runs, 42 RBI, 44 stolen bases and 81 strikeouts in 498 at-bats. He'll be 21 this season.

But the only thing that matters to the Phillies is how their own talent evaluators view these players. And maybe they are thrilled with them.

From my perspective, a minor league system isn't about Quantity or Quality, but Quantity OF Quality. Will all seven prospects the Phillies have shipped out in acquiring Lee and Halladay turn into stars or even everyday major-leaguers? Not likely. But the bigger the pool, the better the odds that one or two of them turn into something special.

But again, these are prospects. And Halladay has proven he is the real deal. And if he pitches like the Halladay of the last four years for the next three (or maybe four, or five) years, it'll be tough to argue that he wasn't worth it.

Still, this would seem to put a tremendous amount of pressure on Domonic Brown, since the Phillies have clung to him so tightly while letting much of the rest of their farm system depart. Now, Brown must be the corner-outfielder-of-the-future  if Jayson Werth departs via free agency, since Michael Taylor is no longer an option. And with Drabek, Knapp and Carrasco all gone, there is no obvious starter-of-the-future ready for next season, when Halladay, Hamels and J.A. Happ will be the only three starters under contract. Francisco was a valuable addition and could provide a stop-gap replacement, perhaps in a platoon, for Werth if he leaves after this season. And keep in mind that corner outfielders are a lot easier to acquire, both in the draft and in free agency, than starting pitchers.

What it boils down to is this: anybody who labels anybody other than Seattle the winner in this whole thing is fooling themselves. Even if Halladay pitches up to his billing, this thing could still easily be a push when all is said and done three or four years from now: I'd expect Taylor to get strong consideration for the Opening Day roster. Drabek still needs to work on his change-up - lefties killed him at Double-A last year - but could be ready to get a shot at the Blue Jays' rotation late next season. And D'Arnaud has tremendous upside, although projecting catchers is always tricky business.

Seattle, on the other hand, now has Cliff Lee to go with Felix Hernandez, which could easily prove to be a better 1-2 punch than Halladay-Hamels.

From a monetary standpoint, Halladay is clearly worth a three-year, $60 million extension.

John Lackey signed a five-year deal that will take him through his 35th birthday, averaging 16.5 to 17.5 million a season.

C.C. Sabathia's seven-year contract will take him through his 34th birthday, averaging roughly $23.1 million per season.

Johan Santana's deal runs through his 34th birthday in 2013 and averages a hair over $22 million a season.

A.J. Burnett's five-year deal that averages $16.5 million runs through his 36th birthday in 2013.

Derek Lowe signed a three-year extension in 2009 at $15 million per year that runs through his 38th birthday

Mark Buehrle signed a four-year contract in 2008 that will pay him $14 million per year through his 32nd birthday.

Ryan Dempster signed a four-year contract in 2009 that will pay him $13 million per season through his 35th birthday.

Amaro has made a bold decision. There is plenty of risk, and plenty of upside.

It will be interesting to watch it unfold over the next three years.

IV. One last thing. . .

Since the Phillies are trading Cliff Lee and his $9 million salary to the Mariners to help accomodate Roy Hallday's salary, it is worth noting that the one thing standing in the way of one year of Halladay-Lee-Hamels might have been the two-year contract that Jamie Moyer signed last offseason that guarantees him $8 million this season.

But it will be also interesting to hear RAJ's explanation of why Joe Blanton wasn't in play (if, in fact, he wasn't). Blanton should receive at least $7 million in arbitration this year, which is just $2 million less than Lee's salary. Yes, $2 million is $2 million, but it really does seem like a negligible amount that could be accounted for in other areas of the team. Plus, as reader David Curran points out, Lee will almost certainly be a Type A free agent at the end of the season, so the Phillies would stand to land a first-round draft pick and a supplemental pick if he departed via free agency. This isn't always what it is cracked up to be: Teams only have so much in their budgets to sign draft picks, and first round picks and supplemental picks command hefty signing bonuses. But you could make the argument that the value the Phillies could have netted with their two additional 2011 draft picks would have made it worthwhile to non-tender Joe Blanton and keep Cliff Lee around for 2010. Plus, here are some of the names who will also be free agents after this season: Josh Beckett, Brandon Webb, Javier Vazquez.

Then again, $2 million is $2 million. And for a team that still needs to add at least one more relief arm and, in an ideal world, another starter, there simply might not have been a way to make up the difference between Blanton's salary and Lee's salary.

It is also worth noting that the three teams involved in this swap are a Pat Gillick Triumverate: He retired as GM of the Blue Jays seven months before they drafted Roy Halladay, and he later went on to serve as GM of the Mariners.