From the moment Ruben Amaro took the GM job following the 2008 World Series victory, he had his eyes set on Roy Halladay.
In the new High Hopes podcast, Jack Fritz and James Seltzer interviewed Amaro about trying acquiring his "white whale" during the 2009 season until they finally landed him.
"I think one of the very first meetings I had with David Montgomery was about acquiring certain players," Amaro said. "I remember talking with David very early on in my tenure that if there was one player we could acquire, that player would be Roy Halladay. Obviously, we didn't know that was going to happen. That was the one that was my white whale.
"As we got into the 2009 season, we knew we needed some higher level starting pitching. We knew we were a good club and a championship caliber club but we needed more pitching. We ended up pushing the envelope on that end and looking for that top of the rotation guy. Roy Halladay was our target or three or four other guys out there who were top of the rotation type talent. Clearly, we thought we had an opportunity to get Roy. I had several conversations with (Blue Jays GM) J.P. Ricciardi at the time. Couldn't get to the finish line and we ended up breaking left and picking up Cliff Lee. It was a deal we thought went very well for us and we had success with that move in not giving up a ton of talent that didn't bite us in the butt until maybe later on. (Carlos) Carrasco ended up being a quality pitcher, but it didn't happen til much further down the road.
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"When we had an opportunity to get (Halladay) in the offseason, we felt like that was the right thing to do. (Alex) Anthopoulos become the GM in Toronto. We had some discussions at the GM meetings and kicked around some possibilities. We did try to resign Cliff Lee to a long-term deal and we were uncomfortable with the amount of money he was asking for at the time. We had an opportunity to go get Roy and we did. One of the premises, unfortunately, about doing that was we kept dumping talent out of our system. We tried to replenish it knowing that we would have to trade Cliff to get him. David Montgomery and I talked about it quite a bit. Unfortunately, it was probably one of those decisions that should not have been made. We would have loved to have kept both of them but we needed to replenish our organization. We ended up getting talent young men who were probably much further away from the majors than we should have made. Obviously, Roy came to us and we got him. That was important to the organization, but it was at some cost. It didn't totally turn out the way we wanted but we felt like we had in Roy probably the best starting pitcher in baseball."
Fritz then inquired about why a deal for Halladay did not happen during the 2009 season.
"At the time, I think J.P. Ricciardi was pretty much set on the level of talent being really really high. We just could not give up both of our best players. If I recall correctly, that was Kyle Drabeck and Dominic Brown and they were our two best prospects in our organization and would have had to give up more. I wasn't prepared to do that. The talent we ended giving up in the Lee deal versus the talent we would have had to give up in the Halladay deal was disproportionate.
"It ended up being a great deal for us. Lee pitched extraordinarily well. I couldn't imagine that Roy would have pitched as well as the way Cliff did. He was absolutely lights out for us and pitched well in the playoffs and World Series. I wasn't really disappointed (that he did not acquire Halladay during the 2009 season)."
