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Amaro traveled long road to Halladay

The photograph freezes two ambitious men in a moment of profound satisfaction: A seated Roy Halladay is in the foreground, his shoulders pointed forward as if he is relieved or exhausted. In the background, blurry, is Ruben Amaro Jr. Also hunched while leaning on a table, Amaro peers at Halladay with a cocked eyebrow, underscored on the same side of his face with a smirk. His conquest is finally complete.

"It was something I couldn't pass up," Roy Halladay said of the chance to join the Phillies. (Clem Murray/Staff Photographer)
"It was something I couldn't pass up," Roy Halladay said of the chance to join the Phillies. (Clem Murray/Staff Photographer)Read more

The photograph freezes two ambitious men in a moment of profound satisfaction: A seated Roy Halladay is in the foreground, his shoulders pointed forward as if he is relieved or exhausted. In the background, blurry, is Ruben Amaro Jr. Also hunched while leaning on a table, Amaro peers at Halladay with a cocked eyebrow, underscored on the same side of his face with a smirk. His conquest is finally complete.

Throughout the Wednesday news conference introducing him as a Phillie, Halladay smiled and spoke quietly about an urgent need to pitch in the World Series, how he literally dreamed about it, how he wanted desperately to play for this team. The general manager finally admitted how much he had wanted the pitcher and for how long.

The trade completed that day came with an unusually lengthy history, requiring nearly a half-year of intermittent flirtation. It was revived last month after collapsing in July and caused a difficult divorce from postseason wizard Cliff Lee - but it was a move necessary to fulfill the unquenched longing of both Amaro and his new prize.

The first attempt

It began July 8, when then-Toronto GM J.P. Ricciardi told ESPN's Buster Olney that he would consider trading Halladay. The former Cy Young Award winner and frequent all-star was scheduled to become a free agent after the 2010 season, and the Jays could not afford him. Fans and columnists in nearly every city that fielded a contending team immediately commenced shouting at their front office to land the pitcher.

Five days later, dozens of baseball writers sat in a St. Louis hotel ballroom, awaiting a morning news conference to announce the all-star starting pitchers. A side door opened, and Halladay walked through with American League manager Joe Maddon. The scribes waited through the formal program, devoted to talk of the next day's exhibition game, then scrambled from their chairs to surround Halladay as he stepped off the dais.

The pitcher was calm and quiet while making his desire clear for the first time. "There's a point in your career where you just need to take the chance and win," he said, microphones and tape recorders brushing his face. "I think at this point I'm ready to take the chance."

As the month progressed, the Phils emerged as one of the most likely destinations. Halladay, who possessed a full no-trade clause and met several times with Ricciardi, made his priorities clear: He wanted a chance to pitch in the postseason, and it would be nice - though not essential - to play for a team that held spring training in Florida. The pitcher lived with his wife and two sons in Odessa, Fla., and wanted to spend February and March with them. (The Phils train in nearby Clearwater.)

The Phils, meanwhile, had seen their starting rotation hobbled by Brett Myers' potentially season-ending hip injury in late June and Cole Hamels' inconsistency. They were a good team in need of a top starter, and Halladay was a top starter seeking a good team.

Beyond that match, though, was Amaro's strong attraction to Halladay's pitching. On Wednesday, the GM finally said what people around him had long whispered when he had admitted to "coveting" Halladay "for a long time."

As reported at the time, talks between Ricciardi and Amaro intensified late in the week of July 20. On Friday, July 24, The Inquirer learned of the Jays' bold asking price: The Phillies could have Halladay in exchange for top prospects Kyle Drabek and Domonic Brown and rookie-of-the-year candidate J.A. Happ. It was later learned that Ricciardi had also requested highly regarded outfielder Anthony Gose.

Even as a means to acquire Halladay, Amaro was uncomfortable with the offer. Over the weekend, he countered with a package of lesser prospects, including catcher Lou Marson, pitcher Carlos Carrasco, infielder Jason Donald, and outfielder Michael Taylor, but Ricciardi remained unmoved.

By Sunday, the Phils were actively exploring alternatives and sent scouts to watch, among others, then-Seattle lefthander Jarrod Washburn and Cleveland lefty Lee. By Wednesday, with Ricciardi's demands firm, the Phillies snatched Lee from the Indians for three of the minor-leaguers whom Toronto did not want, substituting high-ceiling but injured single-A righty Jason Knapp for Taylor in the deal.

The afternoon that he made that deal, Amaro walked into the Phils' clubhouse at Phoenix's Chase Field to applause from several excited players. But while the GM had found an ace, he had lost the one he truly wanted.

"Back in July, when that didn't work out, there was some frustration that set in, or a better word would be disappointment," one member of the front office said last week. "Because you think you've got a real chance at something, and it doesn't happen."

Halladay, who had struggled with agreeing to leave the Blue Jays only to learn that all the turmoil had been for nothing, endured a terrible day that Wednesday. As the Phils were completing the Lee trade, essentially ensuring that Halladay would remain in Toronto, the ace lost to the Mariners, 3-2, pitching seven grueling innings on a 102-degree day, the hottest in Seattle's history.

Two people who were in the Jays' clubhouse that day described Halladay as thoroughly devastated. Last week, the pitcher acknowledged that the difficult decision to consent to a move, followed by the lack of a resolution, had created extreme stress on his wife and sons. And Halladay himself was left deeply unsatisfied. During the World Series, he longed to be on the television, not watching it.

"Believe me, I had quite a few dreams about it," he said.

Creative solutions

The second attempt began near an elevator in Chicago. The annual general managers' meetings convened just days after the World Series, but Amaro - while insisting publicly he would make only modest improvements to his bench and bullpen this winter - had quickly refueled for another run at Halladay.

Ricciardi had been fired, replaced by his former assistant, 32-year-old Alex Anthopoulos. Familiar with his own minor-league prospects after six years with the team, Anthopoulos also knew the Phillies' system well after working with Ricciardi during the July negotiations. A Montreal native with a degree in economics, Anthopoulos met Amaro when both were assistants, Amaro first under Ed Wade, then Pat Gillick.

As Anthopoulos recalled last week, he and several of his Toronto colleagues were waiting for an elevator at the O'Hare Hilton, the site of the GM meetings. Amaro approached with a group of his lieutenants; spotting Anthopoulos, he asked for a private conversation.

"I want to ask you something," Amaro said, according to Anthopoulos.

The two walked down a hallway and chatted about Halladay.

Amaro was direct and aggressive. "What's your asking price?" he said, before offering Anthopoulos a few days to think about his answer and get back to the Phillies.

But the Toronto GM did not need any time; he remembered the player he'd been most impressed with in July.

"We like Drabek," he said.

Drabek, the 22-year-old whom Phillies manager Charlie Manuel likened to Tom Seaver, was nearly - but not totally - untouchable, and Amaro did not want to lose him. But Anthopoulos indicated he could foresee a deal without Brown, the one player Phillies sources say the club was almost totally unwilling to trade.

The two GMs maintained contact through November, looking for different ways to make a deal work.

"Ruben was very aggressive overall," said Anthopoulos. "He would bring up ideas on three-ways and four-ways. He was very honest about what he wanted, and that helped the negotiations, because it helped build trust."

Many of those ideas grew from free-flowing meetings in the executive offices at Citizens Bank Park. The potential holdups to a deal were many - an already high payroll, a farm system weakened by the Lee trade in July - but the GM expressed to his assistants a desire for creative solutions.

"Ruben is very open-minded," said one member of his inner circle. "He creates an atmosphere where people feel free to throw out ideas."

Amaro and others credit Gillick with instilling that trait in his successor, and team insiders said that Gillick was heavily involved in this process.

One of the ideas tossed around, Amaro acknowledged last week, was to shop Joe Blanton. The righthander will probably receive $7 million to $8 million in salary arbitration, making him nearly as expensive as Lee, a relative bargain for 2010 at $9 million.

But in Indianapolis for the winter meetings the week of Dec. 6, the Phils determined they would not receive high-end prospects for Blanton. While continuing to check in with Anthopoulos, the club brainstormed ways to clear payroll and acquire top minor-leaguers to make this work. Clearly, only one move would accomplish both goals: trade Cliff Lee.

Not a no-brainer

"I can't say that it was a no-brainer, because it wasn't," Amaro said last week of adding Halladay by subtracting Lee, the man who had glided effortlessly through his first postseason, treated Yankee Stadium like a beer-league field, and hurried his way through four playoff wins.

But Amaro wanted Halladay more than he wanted any other player. And after a key meeting with Lee's agent, Darek Brauneker, in Indianapolis, the GM felt that Lee would want a market-value contract. He suspected that Halladay would agree to a deeply discounted extension because of his strong desire to play for the Phillies.

On Thursday, a day after the trade, Lee expressed his own strong desire to play in Philadelphia and said he had wanted to sign an extension. The intense and reserved Arkansan had found a team that made him happy, and he believed he would remain there. After all the trades were completed, Lee and Brauneker insisted they were amenable to negotiating a fair contract, while Amaro maintained he could not have afforded Lee.

But Lee, who learned the shocking news he had been traded while driving to a fishing trip on the Mississippi River, ultimately became a casualty of Amaro's and Halladay's mutual fixation.

Following the meeting with Brauneker, Amaro and his staff began to discuss what teams might want Lee and would have attractive prospects to trade. The Phillies benefited from a special familiarity with the Seattle system, most of which was coincidental. Gillick had been general manager of the Blue Jays and Mariners but not recently enough to benefit from inside knowledge. But Phillies assistant general manager Benny Looper had worked in Seattle for two decades, leaving in 2008, and had direct knowledge of the players Amaro eventually requested: pitchers Phillippe Aumont and Juan Ramirez, and outfielder Tyson Gillies. Though those players are highly regarded, many in Seattle believe they were an easy price for Lee.

And because of geographical convenience, the Phils were more familiar with the Mariners' system than that of many other teams. Two of their professional scouts, Jim Fregosi Jr. and Dean Jongewaard, were based on the West Coast, and special assistant Charley Kerfeld made several trips there last season.

For all those reasons, the Phils were able to quickly prepare the framework for a Lee-to-Seattle proposal. According to a source, Amaro first approached Mariners GM Jack Zduriencik on Dec. 9, the penultimate day of the winter meetings, and learned that Zduriencik would indeed be willing to sacrifice prospects for a former Cy Young Award winner and World Series star. And after Lee-to-Seattle appeared doable, talks to obtain Halladay intensified within days.

Talks heat up

Phillies officials left Indianapolis on Thursday confident that what they called "groundwork" had been laid for moves that would soon be completed. But the complex Lee-Halladay trades were far from certain. Anthopoulos returned to Canada tempted by several offers.

"No, I didn't actually expect to trade Halladay to the Phillies by the next week," Anthopoulos said. "We had very positive talks with other clubs."

He declined to name the clubs, but the Los Angeles Angels were widely believed to want Halladay, and the New York Yankees and Boston Red Sox also reportedly expressed interest. But according to people in both the Phils' and Jays' organizations, talks among Philadelphia, Toronto, and Seattle intensified last weekend.

On Sunday, the Phillies requested from the commissioner's office a 72-hour window to negotiate a contract extension. Halladay and his agents flew to Philadelphia. Financial talks did not present an obstacle, because both sides wanted Halladay to be a Phillie. But on Monday, the trade itself remained under discussion.

According to two people familiar with the process, one of the Amaro-led brainstorming sessions produced an idea that might have allowed him to keep Drabek: Maybe the Phils could flip Aumont and Gillies to Toronto, because both were Canadian. In addition to their status as strong prospects, the two players could provide a public-relations boost to the Blue Jays on the day they lost their best player.

Anthopoulos, though, valued baseball skills over nationality. And while he liked the Seattle players, he preferred Drabek. "If a player is talented and happens to be Canadian, that's a bonus for us," he said. "But would we ever acquire someone because he is Canadian? No."

So, by Tuesday the framework was in place. The Phils would lose Drabek but hold onto Brown and add three minor-leaguers for Lee. They signed Halladay to a three-year, $60-million contract extension with vesting options for a fourth season. Toronto would send $6 million to offset Halladay's $15.75 million salary for 2010. And the pitcher, whose wife joined him midweek to explore their new city, was nearly ready to don the uniform he had wanted to wear since July.

One last issue

Fittingly, the final day was not free of tension. Phillies officials quietly predicted a late-afternoon news conference on Wednesday to introduce Halladay. But well after noon, all clubs involved remained quiet. No press releases. No announcements.

Then, at 12:43 p.m., Bob Elliott of the Toronto Sun tweeted: "We're hearing someone involved in the trade flunked their physical."

The next two hours brimmed with Internet innuendo, as rumors emerged that Drabek, who underwent Tommy John surgery, had failed. Or perhaps it was Taylor, who suffered from a sore elbow while playing in Mexico this winter. Reports out of Seattle confirmed that all the Mariners had passed.

At 1:59, an Inquirer reporter asked a team source via text message if the deal was in jeopardy. The response: no.

After another strangely silent hour, the Phils announced the Lee trade. Then, at 3:30 p.m., they sent the news release: "Phillies Acquire Halladay."

It turned out that Toronto, which was set to acquire infielder Brett Wallace from Oakland for Taylor as yet another component to the deal, had last-minute concerns about Wallace's shoulder. Those concerns were resolved, and the trade was made official.

To watch Amaro and Halladay at the news conference that evening was to see two happy and exhausted men. Halladay, coughing frequently while fighting a cold, said, "To feel like you had the chance of getting everything you want, it doesn't happen very often."

Amaro, apparently unable to contain himself, blurted, "Congratulations to us."

That moment fit him perfectly: not always modest but clear about his desires. And Halladay, for whom life as the best pitcher in the best division in baseball was not satisfying enough, wanted this trade just as badly. Both men chased, and both men attained, a reality devised in their dreams.