Originally posted on Phillies Nation  |  Last updated 11/27/11

What grade does Ruben get on the Oswalt trade? Check below. (PHOTO: AP)

After taking over for Pat Gillick following the 2008 World Championship season, Ruben Amaro Jr. hasn’t been lacking in the big-moves department. Roy Halladay, Cliff Lee, Hunter Pence – all his doing. The Ryan Howard extension was his, as well. The Roy Oswalt trade had a big impact on the Phillies.

Overall, I think most believe Amaro has done a hell of a job bringing in top-notch talent and keeping the Phillies as a premier franchise.

Let’s take a look at how each move has turned out for the Phillies in this four-part series. We’ll begin with the starting pitchers.

Roy Halladay trade/extension/Cliff Lee trade:

-Phillies give up Michael Taylor, Travis D’Arnaud, Kyle Drabek to TOR
-Phillies trade Cliff Lee to Seattle for Tyson Gillies, Phillippe Aumont, J.C. Ramirez
-3 yr/$60 million contract with 4th year option at $20 million

If the Phillies had not traded Cliff Lee while obtaining Halladay, this would be an A+ move for the team. Although the two trades were considered separate deals, they still came hand in hand in the eyes of the fans. Sure, the Phillies got Lee back in free agency, but that could have been avoided. Overall, still a solid move as Aumont works his way up the ranks in the Phillies system. Drabek and Taylor have struggled and while D’Arnaud looks like he could be a good catcher, he’s blocked in Toronto.

Grade: B+

Cliff Lee signing:
-5 yr/$120 million contract with 6th year club option at $27.5 million ($12.5MM buyout)

Was the biggest move of the offseason prior to 2011, hands down. The Phillies were not thought to be suitors, but Amaro kept it low-key, talking with Lee’s representation and making an underground move to bring in the best free agent pitcher on the market. He also regained some brownie points from the fan base for getting the guy back that never wanted to leave in the first place. It’s hard to grade it at this point because there are still several years remaining on the deal, however, after one season, it’s looking sweet.

Grade: A

Joe Blanton signing:
-3 yr/$24 million contract

Ugh. Those three letters pretty much sum up one of the worst moves made by Ruben Amaro as GM of the Phillies. Amaro preached cost certainty and the innings-eating Blanton would give them that and, hopefully, continue on with his 190-200 innings-per-season pace. And, $8 million per season usually isn’t awful for a fourth or fifth starter, however, a 4.82 ERA in 2010 and a 5.01 ERA in 2011 with injuries is not what they envisioned.

Grade: F

Cole Hamels signing:
-3 yr/$20.5 million contract (2009-2011)

Amaro bought out several arbitration years with a team friendly deal. Looking back, there was one shaky year for Hamels (2009), with two All-Star caliber seasons to follow. In 2011, Hamels finished fifth in the Cy Young voting. Hamels made less per season than Blanton, for about five times the pitcher. Great signing. Now, Amaro will have to make good on keeping Hamels around as he heads to arbitration again.

Grade: A

Roy Oswalt trade:
-Phillies trade Anthony Gose, Jonathan Villar, and J.A Happ
-Phillies receive $11 million as part of trade

A good, but not great, move. Oswalt gave them a sensational second half of 2010, giving the Phillies a solid three-headed monster heading into the postseason. Obviously, 2011 was a different story as he battled a serious back ailment, likely ending his time in Philadelphia. For what they gave up, the Phillies got a steal. Happ has been just short of hideous, and while Gose looks like a player, however he’s got a ways to go. Had Oswalt stayed healthy throughout, this could have been an A. But, 2011 just wasn’t not a good season for Oswalt.

Grade: B-

Jamie Moyer signing:
-2 yr/$13 million contract (2009-10)

When you sign a guy pushing 50 to a two-year deal, you’re playing with fire. Amaro got burned by Jamie Moyer, as he gave them 44 starts in two season with an ERA near five. Sure, it’s like having a second pitching coach, but they really needed help on the field, not off it. He simply did not put up numbers on par with a $13 million deal. Moyer was/is the consummate professional, but it was just downright stupid to give him that kind of contract.

Grade: D

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