How the Phillies traded for Roy Halladay

December 16th, 2021

The Phillies completed one of the greatest trades in franchise history on Dec. 16, 2009, when they acquired Roy Halladay from the Toronto Blue Jays for Kyle Drabek, Travis d’Arnaud and Michael Taylor. The weeks and months leading up to the trade were detailed in the best-selling biography “Doc: The Life of Roy Halladay.”

This excerpt from Doc: The Life of Roy Halladay by Todd Zolecki is reprinted with the permission of Triumph Books. For more information and to order a copy, please visit


THE BLUE JAYS FIRED [J.P.] Ricciardi on the second-to-final day of the [2009] season. They replaced him with assistant general manager Alex Anthopoulos. He was in his new role less than a month when Halladay and his representatives requested a meeting. Late in October, as [Cliff] Lee and the Phillies charged toward their second consecutive National League pennant, Blue Jays president Paul Beeston, Anthopoulos, the Halladays, and Halladay’s agents scheduled a dinner at Roy’s Restaurant, a Hawaiian fusion joint in Tampa. Anthopoulos canceled at the last minute because he fell ill, but he talked to Halladay beforehand. Halladay repeated the same message to Beeston.

“Look, if you guys are rebuilding, my clock is getting short,” Halladay said. “I don’t know how long I have and I don’t want to go through another rebuilding process. I would love nothing more than to win a World Series championship in Toronto, but I don’t know that I have that time. So, I would really prefer that you guys would push me to one of these two teams.”

He wanted to play for the Phillies or Yankees. Anthopoulos understood.

“As far as I was concerned he was six months away from being able to choose where he wanted to play,” he said, referring to free agency. “I didn’t begrudge him at all. And he earned his no-trade clause. He gave the club plenty of hometown discounts, and he also did a lot in the off-season to try and recruit. He really wanted to win in Toronto. He really cared about it. I remember, in any off-season, we would call and say, ‘Hey, can you come up? We’re bringing up Gil Meche,’ or, ‘We’re bringing in A.J. Burnett.’ Done, he was there. I remember one time in the winter, we may have been going to a Leaf game. I was in the car with him, he was saying at the time, ‘I wouldn’t want to play in Boston or New York. This is where I want to win. This is what I want to do.’ He really legitimately cared about the organization.

“This points to Roy’s class. I remember when he first talked to me and Paul when he requested the trade. He said, ‘If there are any concerns for the organization, PR, optics, I understand.’ He wasn’t being arrogant about it, but he said, ‘Look, I understand. I’m a name here. I’ll wear it. Put it all on me.’ Which, I’ve got to tell you, was pretty amazing. ‘Put it all on me. I’m driving this. I’m doing this.’ This is 100 percent, I’m accountable. This is my responsibility. I do not want the organization to suffer. We didn’t even bring it up, ‘We’re concerned,’ this or that. None of that. It didn’t even come out of our mouths. He just volunteered.”

[Ruben] Amaro [Jr.] reconnected with Anthopoulos at the GM meetings in November. Amaro, [assistant general manager Scott] Proefrock, and other Phillies’ officials were stepping onto an elevator when Anthopoulos approached. He asked to speak to Amaro. Before the elevator doors closed, Amaro stepped off. Amaro reiterated to Anthopoulos that he wanted Halladay, even though he had Lee.

“We’re interested in doing something,” he said.

Anthopoulos mentioned the names that would get the ball rolling again: [Domonic] Brown and [Kyle] Drabek. The Phillies pushed back. Anthopoulos tried to line up something with the Angels, White Sox, and Rays. His efforts proved futile. Halladay insisted on the Phillies or Yankees. They were two World Series-caliber teams that trained close to his home outside of Tampa. The Phillies won two consecutive National League pennants, including the ’08 World Series. They held spring training in Clearwater, a 15-minute drive from the Blue Jays’ facility in Dunedin. The Yankees just beat them in the ’09 World Series. They trained in Tampa.

The Blue Jays started to push the White Sox and Angels, but both teams trained in Arizona. It was not going to happen. Halladay’s agents became frustrated. They exercised some leverage. Jeff Berry, a partner at CAA who worked with Halladay’s long-time point man, Greg Landry, spoke with ESPN’s Buster Olney.

“Once Roy reports to spring training as a member of the Blue Jays,” he told him, “from that point forward he will not approve or even discuss any potential trade scenario. This will eliminate a repeat of the distracting media frenzy of 2009 for both Roy and his teammates, and will allow Roy to focus on pitching at the exceptional level Jays fans have come to expect.”

It was a clear message to Anthopoulos: forget about the White Sox and Angels and get something done with the Phillies or Yankees. If not, Halladay leaves after 2010 and Toronto receives only draft picks as compensation.

“That was authentic,” Berry said. “That wasn’t a bluff. Roy was genuine and they knew that. I remember going to his house to meet with him in person and we were meeting with him to discuss how we were going to approach the trade. You walk up to his house and we go upstairs and walk past the Cy Youngs and the All-Stars, and Roy’s in jeans and cowboy boots, larger than life as always, and very calm. He had thought a lot about it. Those are the two places he thought about going.”

The winter meetings arrived. There were rumors the Rays could send outfielder B.J. Upton and prospects Wade Davis and Desmond Jennings to Toronto. Amaro asked Anthopoulos if the reports were true. He would not say.

“It was an impossible market,” Anthopoulos said. “Every time I asked about other teams it was just like, ‘No.’ Which was fine. I don’t begrudge that he had it, but from there I’ve never given out a no-trade clause. We were caught in a tough spot. He made it very clear, ‘I’m leaving. There’s nothing you can do to talk me into staying. I can’t emphasize this enough. You can’t extend me. You can offer me all the money in the world. I need to win. I want to win.’ You’re weighing everything against two draft picks. The line would have to be significantly better than two picks.”

Anthopoulos wanted Drabek, Brown, [Anthony] Gose, and [Travis] d’Arnaud, essentially the same deal as the one in July, except d’Arnaud replaced [J.A.] Happ. The Phillies agreed to include Drabek. Things were progressing, although the Phillies worked on Plan B just in case. They were negotiating with Lee about a contract extension, but their feelings soured at one point. Players traded in the middle of a multiyear deal can request a trade. Lee’s agent, Darek Braunecker, indicated after the Phillies acquired him that they would not seek compensation from the Phillies as a goodwill gesture to not exercise their right. Then they did.

“That sort of set everybody off,” Proefrock said.

The Blue Jays made another offer: Drabek, d’Arnaud, Taylor, and Joe Blanton. It seemed more palatable to the Phillies, but they did not want to trade Blanton. He went 12–8 with a 4.05 ERA in 31 starts in 2009. He was not a top-of-the-rotation starter like Halladay, Lee, or [Cole] Hamels, but he could pitch every five days and throw six innings. There was value in that.

“Blanton still had some thunder in him,” Amaro said.

The Phillies convinced Toronto to remove Blanton, giving them a framework for a deal: Drabek, d’Arnaud, and Taylor for Halladay.

Now the hard part. The Phillies needed to accomplish three things before they crossed the finish line: 1) Halladay needed to agree to a contract extension, 2) he needed to pass a physical, 3) the Phillies needed to trade Lee. [Phillies president David] Montgomery told Amaro that he needed to trade somebody to restock the farm system. Nobody could fetch talent like Lee, who made only $9 million in 2009.

“It’s something I didn’t necessarily want to do,” Amaro said. “That was kind of part of the deal. If you’re going to keep dumping some of this talent out of the system, you better replenish. We had to answer to some people. It wasn’t that we didn’t want Cliff on our club and it wasn’t that I didn’t want a super rotation.”

Back in Florida, Halladay, [his wife] Brandy, and the boys boarded their boat at a nearby marina. They ordered pizza, made popcorn, and watched movies. They spent the night talking about the future. They wanted to play for the Phillies or Yankees, but if it could not happen, maybe they could play for the White Sox. The Sox won the AL Central in 2008 before losing 83 games in ’09. But they loved Chicago. Brandy went to high school there. She knew people there. Could it work? Yes, they said. They could play for the White Sox for one year, then hit free agency, and choose where they wanted to play.

“It was just kind of the start of a transition,” Brandy said.

The Halladays decided they would call Landry and tell him that they would accept a trade to Chicago. Halladay’s phone rang first. Toronto had an agreement in place with the Phillies. They had a 72-hour window to agree to a contract extension. The Halladays flew to Philadelphia. Landry, Berry, and fellow CAA partner Brodie Van Wagenen joined them there.

“We landed, they took us off the back of the plane in a black car and drove us off the tarmac,” Brandy said. “I’m like, ‘Is this the CIA? What is this?’”

The Halladays pulled up to the Ritz-Carlton in Center City, checked into their room, and did not leave for two days. (If anybody called the hotel looking for him, they probably would not find him. Halladay frequently used the alias “Jim Nasium” when he stayed in hotels.) Landry, Berry, and Van Wagenen shuttled back and forth from the hotel to Citizens Bank Park, where they met with Amaro and Proefrock in a conference room outside Amaro’s office. They negotiated with the Phillies for about an hour or so, then returned to the hotel to talk with the Halladays. They probably made four trips to the ballpark in two days.

CAA wanted Halladay to sign an extension that matched any potential contract he could sign if he hit free agency following the 2010 season. They looked for a five-year, $90 million extension (or $18 million per season), on top of the $15.75 million he would make in 2010. The Phillies said no. First, this was not a free-agent situation. Second, they had a policy of not signing a pitcher to more than three years. Amaro countered with a three-year offer worth about $54 million. CAA rejected it.

“There were choke points,” said Van Wagenen, who left CAA to become the New York Mets’ general manager before the 2019 season. “From the agent’s perspective, you’re working on trying to accomplish the goals for the player and the family. Now I have a perspective from a team’s standpoint of negotiating on the other side of that. When you get to that point, you want the player. You want that player to be a part of your history. But it’s high stress because you don’t know the outcome. Everyone wants the same outcome at that point because you don’t get that far if both sides don’t want to make it happen. At the end of the day, from the agent’s perspective, when you have two parties that want to make something happen, I always viewed that it was our job to make sure that happened.”

Negotiations stalled and the Phillies became pessimistic. Proefrock suggested to Amaro that he circle back to Braunecker to heat up extension talks with Lee. Halladay sensed the stall too. He told his agents to forget the extra years and make something happen with three.

“When John Wayne wants to see this happen, you want to make this happen,” Berry said.

Amaro made concessions. The extension had to average $20 million per season. The Phillies offered three years and $60 million. Halladay agreed. He passed his physical. The Phillies then rushed into a trade, shipping Lee to Seattle for prospects Phillippe Aumont, Tyson Gillies, and J.C. Ramírez. The deal flopped. Aumont had a 6.80 ERA in 46 career appearances in the big leagues. Gillies never reached the big leagues. Ramírez had a 4.71 ERA in 142 career appearances with five different organizations from 2013 to ’19.

“My only regret is that we didn’t take the appropriate time,” Amaro said. “There was a feeling that if we allowed this to drift, the fans would have a tough time accepting it. Why would you now move this guy? So we had to make it sort of look like it was a three-way deal.”

It was a bittersweet moment for Anthopoulos.

“Roy did everything,” he said. “Whatever he needed to do, he tried and tried and tried and tried. For me, I look back on having generational talents like Roy Halladay and Carlos Delgado. We were never able to get to the playoffs. The shame of it for me is when you think of Roy Halladay and his greatest moments, you’re thinking playoffs with the Phillies. It’s not his fault. We never got those guys to that stage. When you talk about the legacies of players, it’s just rare that you have a chance to have these guys. I’m really happy for him that he got his opportunity. You wish it would have been for a longer period of time at an elite level, but he had that opportunity on the big stage to do it and dominate and everybody appreciated how great he was.”

On December 16, Halladay pulled on his Phillies jersey and cap at Citizens Bank Park. He smiled.

“This is where I wanted to be,” he said.