Philadelphia Phillies Close to Extension with Master Assembler Ruben Amaro Jr.

Just a day after the Philadelphia Phillies agreed to a contract extension with the manager that has led them to four consecutive National League East pennants, the team has agreed in principle to sign its general manager, Ruben Amaro Jr., to a contract extension.

First reported by Todd Zolecki of MLB.com, the parameters of the extension aren’t clear at the moment. At the very least, the deal is expected to have a minimum of two years—the same guaranteed years to Charlie Manuel—and with Amaro just 46 years old, could extend well beyond that.

As with many general managers, Amaro’s tenure in Philadelphia has been spotted with good and bad deals. After taking over for Pat Gillick following the Phillies’ 2008 championship run, Amaro was faced with the task of introducing young talent to an aging team, while still putting a championship-caliber team on the field. With that in mind, Amaro has made a flurry of trades and signings.

Before the 2009 season, Amaro’s first difficult decision revolved around letting declining outfielder and fan favorite Pat Burrell walk via free agency. Not so long after that, Amaro replaced him with former Seattle Mariners left fielder Raul Ibanez, signing him to a three-year, $31.5 million contract.

As his first free-agent signing, the deal was criticized harshly. Many fans and analysts alike believed that the deal, which guaranteed three years to a 36-year-old outfielder, was an overpay in all aspects of the contract. Though Ibanez quieted the critics for a while with a tremendous first half, he proved them right by slumping through his contract ever since.

In much of the same fashion, he was criticized for offering the oldest pitcher in baseball, Jamie Moyer, a multi-year contract that paid him more than $6 million a season. Though he was a quality pitcher for the Phillies in that span of time, Amaro began showing a troubling trend of offering unnecessary contract years.

Not every deal was a bad one in his first offseason as the Phillies general manager, however. He locked up a couple of integral parts of the Phillies World Series run, agreeing to contract extensions with slugging first baseman Ryan Howard and World Series MVP Cole Hamels. At $54 million and $20.5 million respectively, these deals were received in a much gentler light.

In his first trade as the Phillies general manager, Amaro swapped a pair of five-tool outfielders, when he sent Greg Golson to the Texas Rangers for power-threat John Mayberry Jr. While the latter has yet to reach his potential, the deal was favored in Philadelphia, as many had soured on Golson’s ability.

None of those deals really put Amaro’s name on the map, however. That would be done during the season. After months of speculation on the Phillies interest in Toronto Blue Jays ace Roy Halladay, Amaro pulled off a surprise move at the trade deadline, when he sent four talented prospects to the Cleveland Indians for their ace, Cliff Lee, and fourth outfielder Ben Francisco.

Of course, that would just be the beginning of the Lee drama.

He wasn’t finished bolstering the Phillies rotation that season, however. After spending the first half of the season out of baseball, Amaro agreed to sign former Cy Young Award winner Pedro Martinez to a deal that guaranteed him through the end of the 2009 season. Martinez proved to be a lift for the Phillies, and he and Lee helped lead the Phillies back to the World Series, though they couldn’t bring the trophy back to Philadelphia.

The offseason that followed would put Amaro on the map in Philadelphia—whether it was good or bad was yet to be determined. After months of pursuit, the Phillies finally landed Halladay, but the cost—Cliff Lee—was almost too much for some fans to bear. Amaro would send top pitching prospect Kyle Drabek and two others to the Blue Jays, and in an effort to restock his own farm system, send Lee to Seattle for three prospects, all of who would underachieve in their first season in the Phillies organization.

He would sign Halladay to a very team-friendly extension, in regards to one of the best pitchers in baseball, inking him to a three-year, $60 million extension with an option. Despite that, trading Lee, a new fan favorite, was a tough decision and Amaro fell out of favor with many Phillies fans.

Though it was the offseason’s blockbuster, it was only one of a few moves for Amaro. He continued his disturbing trend of offering too many guaranteed years for veteran free agents, retooling the bench and bullpen by signing Ross Gload, Brian Schnieder and Danys Baez to two-year contracts, and adding utility man Juan Castro and starter-turned-reliever Jose Contreras to major league deals as well. The most productive free-agent signing of the offseason was Placido Polanco, who took his Gold Glove defense at second base and showed that third base was no problem at all.

The most underrated move of that offseason was probably in the form of Wilson Valdez, who Amaro had signed to a minor league deal as depth. When Jimmy Rollins and Chase Utley would go down with injuries, Valdez would prove to be an integral part of the team.  

Despite being happy with the structure of his team, come the trade deadline, injuries had set in and Amaro felt the need to make a move to shake the Phillies up a bit. He continued one of his better trends—acquiring aces—by sending J.A. Happ and two prospects to the Houston Astros for Roy Oswalt and $11 million.

With three aces on his staff, the Phillies fans began to rally behind Amaro after a disappointing end to the 2010 season. Entering his third offseason as the Phillies general manager, he had one true task to solve now—who plays right field?

Jayson Werth, who had managed to stay healthy and put together another tremendous season, had become a free agent, and the Phillies needed to figure out who would be playing right field come Opening Day 2011. Was top prospect Domonic Brown ready? Could they give Ben Francisco a shot? As it turns out, the Washington Nationals would make that decision easy by signing Werth to a mega-deal the Phillies couldn’t begin to match.

With their right field situation being solved by default, Amaro would go on to stun the baseball world and bring yet another ace, Lee, back to Philadelphia, assembling the kind of rotation that comes around in baseball only once in a while.

And that, of course, is where the Phillies team stands today. Despite having “four aces,” Amaro’s work is still cut out for him. With mounting injury concerns, will he have to make a move to reinforce the Phillies infield? This offseason holds an even darker outlook, as he’ll have to negotiate deals with Ryan Madson, Cole Hamels and Jimmy Rollins, as well as make tough decisions on the likes of Brad Lidge and Raul Ibanez.

Fear not though, Philadelphia. The Phillies are in good hands. Or are they?

Though it’s hard to argue that Amaro has done a bad job during his tenure in Philadelphia, as the Phillies have done nothing but win, the team is still without a World Series ring under his reign. He’s shown that troubling trend of offering too many guaranteed years, and his extension of Ryan Howard is easily one of the most lopsided contracts in baseball.

On the other hand, the Phillies have a lot to look forward to under his reign. He’s shown that he is a shrewd negotiator and has drafted well, leading the Phillies to one of the most talented, young farm systems in baseball.

Some of his moves may be difficult to understand, but with an ever-expanding payroll and talented young farm system, the Phillies are more than sure that Ruben Amaro Jr. is the right guy for the job moving forward.

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