Dealing Halladay was complicated process

Dealing Halladay was complicated process

TORONTO -- With one bold stroke, Blue Jays general manager Alex Anthopoulos has reshaped the future of an organization. Baseball's new kid on the block helped design and execute one of the most complicated trades in recent history, showing early on that he means business.

Two Cy Young winners. Four teams. Nine players. All included in a series of deals that sent star pitcher Roy Halladay to the Phillies, left-hander Cliff Lee to the Mariners and a group of highly-touted prospects to Toronto, Philadelphia and Oakland.

"Everybody now knows that Alex Anthopoulos is the real thing," Blue Jays president and CEO Paul Beeston said with a smile on Wednesday.

It was Beeston who flew to Baltimore on the final weekend of the regular season to dismiss former Blue Jays general manager J.P. Ricciardi and hand the job to the 32-year-old Anthopoulos. The rookie GM had worked as an assistant under Ricciardi and watched his former boss hang on to Halladay after trying to deal the ace prior to the July 31 Trade Deadline last year.

At that time, the Phillies made a strong push to land Halladay, but instead acquired Lee in a blockbuster trade with the Indians after Toronto refused to lower its asking price. Even after Lee was dominating for Philadelphia throughout the 2009 playoffs, Phillies general manager Ruben Amaro Jr. continued to have interest in Halladay.

How it began

In November, during the General Managers' Meetings in Chicago, Amaro revisited the topic with Anthopoulos, setting the stage for one of the winter's most creative transactions.

"I remember he pulled me aside -- we were on our way to a meeting," Anthopoulos recalled. "He just asked me what my thoughts were with respect to Roy and a trade and what I thought the cost might be. I remember at the time, he had talked about if I could get back to him.

"Obviously, with the work that we had done last year and how thoroughly we had scouted the Phillies organization trying to prepare for a trade, I was able to give him a response fairly quickly with respect to some of the names that needed to be part of it. That's where it started."

Anthopoulos' approach with Amaro was the same he took with every club interested in Halladay. The rookie general manager informed teams what players interested the Blue Jays, rather than fielding offers from teams or having teams try to sell Toronto on any prospects. For Anthopoulos, it was about quality, and not about a large quanity of average players.

If the Blue Jays' asking price was too steep, Anthopoulos looked for another route. By bringing in other teams, he felt he could find a way to reel in the type of young, controllable, impact players that would prove vital in strengthening Toronto's foundation.

"We weren't sitting back and seeing what was being offered," Anthopoulos said. "We were the ones that asked for specific players and we tried to get the best value that we could. That's why we really explored a lot of three-, four-, five-team deals with all kinds of scenarios to make sure that we could extract the best value."

Laying the groundwork

A few weeks before the Winter Meetings on Dec. 7-10, Anthopoulos approached the A's and informed them that he was getting deeper into trade talks with the Phillies on a potential Halladay deal. Anthopoulos wanted to know if Oakland would be willing to part with infield prospect Brett Wallace in exchange for one of the Phillies' prospects, outfielder Michael Taylor.

With that seed planted, Anthopoulos requested formal offers from any teams still interested in dealing for Halladay by Friday, Dec. 4. With offers in hand, Anthopoulos convened with Toronto's front office on the weekend before the Meetings. They worked on narrowing down the list of suitors and coming closer to a package of prospects strong enough to convince them to trade Halladay away.

At the Winter Meetings, Anthopoulos kept a low profile and held private meetings with a handful of clubs -- only allowing two representatives of a team at the most into his suite in an effort to control information leaks. By the end of the Meetings, it was reported that the Angels and Phillies were the front-runners for Halladay, but more teams were involved.

"There's no question it was very fluid, there was a lot of teams involved, a lot of back-and-forth dialogue," Anthopoulos said. "There were certain scenarios where we could've gotten five, six, seven players. Again, we didn't feel the quality was there. It comes back to the philosophy of trying to acquire players that would be hard to acquire via trade."

Anthopoulos said that the Blue Jays and Phillies went through a number of possible scenarios. In one brainstorm, Lee would have actually been sent to Toronto, which would have then tried to flip him to another team for prospects. One complication for the Phillies was the difference in Lee's salary ($9 million) and Halladay's salary ($15.75 million) for 2010.

Making it work

Toward the end of the Winter Meetings, Amaro approached Mariners general manager Jack Zduriencik about a possible deal that would send Lee to Seattle. That ignited a second layer that was integral in the deal for Halladay. By trading Lee, Philadelphia could obtain prospects to cushion the blow of the ones lost in the Halladay swap and the original deal involving Lee in July.

Lee's contract does not include a no-trade clause, allowing the Phillies to move him without gaining approval first. As for Halladay, he has a full no-trade clause and any deal had to be cleared by him beforehand. That limited the number of possible trading partners for the Jays, but the Phillies were always one of Halladay's top choices.

"Roy ultimately had control over the process," Anthopoulos said.

Another critical aspect to the trade for the Phillies was signing Halladay to an extension. If the Phillies were going to trade Lee and send Taylor, prized pitching prospect Kyle Drabek and catching prospect Travis D'Arnaud to Toronto -- the group the Jays asked for and ultimately received -- Philadelphia needed to increase the incoming value by extending Halladay.

The Blue Jays were reluctant to grant a window in which to discuss an extension, but agreed to it in order to complete the deal. In the end, Halladay signed a three-year pact worth $60 million with a vesting option worth $20 million for 2014. Toronto also sent $6 million to Philadelphia to help cover the money Halladay was owed in 2010.

"I explained to Roy that ideally I wouldn't want to grant a window for an extension," Anthopoulos said. "It certainly makes things more complicated. Deals can fall apart that way. I told the clubs that as well. I explained it to Roy, but Roy told me that he was open to both. Whatever would help to facilitate a trade, he was willing to do it. Certainly, with Philadelphia in negotiations that we made, it was something that they absolutely needed to have."

As talks became more serious between the Blue Jays, Phillies and Mariners, Toronto again approached the A's about Wallace -- a player the Jays have coveted for a few years. Oakland, which acquired Wallace from the Cardinals in the July trade that sent slugger Matt Holliday to St. Louis, eventually agreed to a side deal that would send Wallace to the Jays for Taylor.

"It did not come together fast at all," Anthopoulos said. "Oakland did not give this player up easily. I think they deliberated on it for a long time. This was not a quick, 'Yes.' This took weeks. We had a lot of debate, too, because Taylor is a great player as well."

The finishing touches

On Saturday, all the teams had reached a deal. The Blue Jays would receive Drabek, D'Arnaud and Taylor from the Phillies, and then would send Taylor to the A's for Wallace. The Phillies would land Halladay and cash from Toronto, and would then trade Lee to the Mariners for prospects Phillippe Aumont, Tyson Gillies and J.C. Ramirez.

Blue Jays ownership approved the deal on Sunday morning, leaving Halladay's extension talks and physicals for all the players as the final obstacles. In terms of the extension, Halladay's strong desire to win, combined with the fact that being the highest-paid pitcher in baseball is hardly a priority of his, led Anthopoulos to believe that would be a quick process.

"There was a comfort level on my end," Anthopoulos said, "knowing how Roy felt about Philadelphia and the fact that they were a World Series team the last two years and knowing that Roy truly is a guy that's not about the money."

Halladay reached an agreement with the Phillies on Tuesday, setting off the complicated process of shuffling all the players to various locations to see team trainers and doctors. Early on Wednesday, reports surfaced that one of the Minor Leaguers failed his physical, setting off widespread speculation. The delay turned out to be the Jays' wanting an MRI on one of Wallace's shoulders, and it simply took longer than expected.

By 5 p.m. ET, press releases were out and news conferences were being called, bringing an end to a complex and dramatic trade that began taking shape in July. For Anthopoulos, less than three months on the job, he might have already swung the defining move of his career.

"I've not known a guy who works as hard as he has," Beeston said. "I think they know that he's somebody who will negotiate hard. He does not just give things away."

Jordan Bastian is a reporter for This story was not subject to the approval of Major League Baseball or its clubs.