Phils' GM Amaro: Bold style

CLEARWATER, Fla. - Whether you considered the series of trades last winter that sent Cliff Lee to Seattle and brought Roy Halladay to the Phillies' genius or lunacy, you must admit this: Ruben Amaro Jr. was not afraid to be bold.

Just more than a month into the winter following his first season as Phillies general manager, Amaro executed a deal that will help to define his tenure, and revealed much about his style in ways that allow us to better predict how he will handle future decisions. When Amaro identifies a player he wants, he quickly decides what the player is worth to the Phils, in dollar and trade value. His decision made, he barrels toward a resolution. Whether the public approves or disapproves, Amaro is usually unmoved, secure in his actions.

The trades last winter generated considerable discussion in Philadelphia. After trying and failing to land Toronto ace Halladay in July and acquiring Cleveland's Lee instead, Amaro refocused on Halladay immediately after the World Series. During the general managers' meetings in early November, Amaro approached new Toronto general manager Alex Anthopoulos near an elevator at the Chicago O'Hare Hilton and posed a straightforward question: "What do you want for Halladay?"

Anthopoulos' immediate reply? Kyle Drabek. Anthopoulos made it clear that Toronto was not going to make the deal without getting the Phils' top pitching prospect. While not an easy thing for Amaro to do, he was not going to allow the request to stall his pursuit of the long-coveted Halladay.

Despite the two GMs' wanting to make a deal and a player in Halladay who longed to play for the Phillies, two major obstacles remained - and Amaro blew through them without decelerating. First, because the Phils had already sacrificed many of their top prospects in the Lee deal and would lose Drabek in any Halladay trade, Amaro would have to find a way to partially restock the system. Second, with a payroll already among the highest in baseball, the GM needed to find a way to acquire baseball's best pitcher without exploding his budget.

The team first tried to address the latter issue during the winter meetings in December, when it floated the possibility of trading Joe Blanton. Blanton ultimately signed a contract extension with the team for three years, $24 million, but at that time he appeared due to make roughly $9 million in salary arbitration. If the Phils could have traded Blanton for decent prospects, they would have found a way to keep Halladay and Lee in the same rotation, replenish the farm system somewhat, and keep the big-league payroll reasonable.

There is a reason that sounded too good to be true - it was. Though Blanton is a valuable and consistent pitcher, no team was willing to both pay his salary and trade desirable minor-leaguers. The Phils moved on to the idea of trading Lee after meeting with the pitcher's agent Dec. 9 to discuss a possible long-term contract extension.

The principles in that meeting left with opposite interpretations. Amaro and the Phils claimed the conversation convinced them they could not afford Lee's contract demands, and led them to shop their World Series ace. Lee and agent Derek Brauneker said they believed the talks were preliminary and ongoing, and they expected Lee to spend the rest of his career as a Phillie.

Whatever happened in that room, the meeting essentially ended Lee's brief and dynamic time as a Phillie. The next day, Dec. 10, Amaro approached new Seattle general manager Jack Zduriencik and asked if that team would be interested in acquiring Lee, who had one more season until free agency.

Because assistant general manager Benny Looper spent 20 years in the Seattle front office, leaving for the Phillies in 2008, he was intimately familiar with its farm system. By early the following week, the framework was in place for what ultimately became the final deal:

Halladay and $6 million went from Toronto to Philadelphia. The Phillies quickly signed Halladay to a three-year, $60 million extension that included a $20 million vesting option for a fourth season - a contract that fell well below Halladay's potential market value as a free agent, which he would have been after the season.

Drabek, catching prospect Travis d'Arnaud, and outfield prospect Michael Taylor went from the Phils to the Blue Jays. (Toronto immediately flipped Taylor to Oakland for infielder Brett Wallace.)

Seattle acquired Lee for prospects Phillippe Aumont, Tyson Gillies, and J.C. Ramirez.

Even before these moves were finalized, many in the public began to wonder why the Phils couldn't have restocked the farm some other time and paid Lee the $9 million owed to him in 2010. Then they could enjoy a potentially legendary rotation for one season, before the talented but aging position players began to decline, and before the possible departure of free-agent-to-be Jayson Werth this winter.

When the deals were finally announced at a Citizens Bank Park news conference Dec. 16, Amaro and team president Dave Montgomery emphasized the farm system element.

"We could have kept both of them , but it was a baseball decision for me and our organization and the people in the organization," Amaro said that day. "We could not leave the cupboard bare. If we had just acquired Roy and not moved Lee, we would have lost seven of the best 10 prospects in our organization. That is not the way you do business in baseball."

"Why are we where we are today?" Montgomery said, reminding reporters that homegrown players were essential to the team's current success. "May I suggest Jimmy Rollins? May I suggest Chase Utley?"

While that argument certainly pressures Aumont, Gillies, and Ramirez to succeed, the reasoning was sound. Why would the Phillies risk mortgaging their future when they could still have a terrific rotation made up of Halladay, Cole Hamels, Blanton, J.A. Happ, and Jamie Moyer, Kyle Kendrick or another fifth starter?

Several months later, it is easy to make a strong and logical argument that the Phils should have kept Lee. It is just as easy to argue that Amaro's decision to simultaneously consider the present and future was the best course.

What can be divined from the series of trades without dispute: Amaro and ownership made a brash gamble by so quickly dismissing the chance to have both Halladay and Lee for one year. It was a gamble based on the belief that Hamels would rebound after a disappointing 2009 season and combine with Halladay to form a top 1-2, righty/lefty combo. It was founded in the assumption, likely accurate, that the Phils were the best team in the National League East with or without Lee.

It will take at least one full season before we can accurately evaluate the trades and say with greater accuracy whether they were admirably aggressive or just hasty. But Amaro's gamble, which will be cited as either the secret to the Phils' success or the beginning of their downfall, can already be labeled characteristically bold.