Ruben Tuesdays: Happy Halladays

Welcome to another edition of Ruben Tuesdays: A weekly look back at the greatest moves made by the Phillies’ former general manager Ruben Amaro. In honor of today’s Hall of Fame announcement, I’ll discuss the time Amaro brought a future Hall of Fame pitcher to Philadelphia.

Roy Halladay played 12 seasons in Toronto, where he was a six-time All-Star and won a Cy Young Award. However, the Blue Jays had never qualified for the postseason during his time with the team. In 2009, with the end of his contract looming, he made it known that he’d be perfectly okay with moving on to a place where he could actually experience playoff baseball. Being polite Canadians, the Blue Jays tried to accommodate their ace’s wishes, and began to negotiate with his team of preference: The Philadelphia Phillies.

In today’s age of top free agents not being enamored with Philadelphia, it may seem hard to believe that one of the best players in baseball actually longed to join the Phillies. Back in 2009, the Phillies were the defending World Champions, and actually seen as a top destination. Additionally, Halladay’s offseason home was near the Phillies’ Spring Training base of Clearwater.

The Blue Jays wanted to be accommodating, but they weren’t about to give away an ace pitcher either. They understandably asked for a massive return, but Amaro was reluctant to include the team’s top prospect: Future All Star Domonic Brown.

Photo by Hunter Martin/Getty Images

Fortunately for the Phillies, another Cy Young Award winner happened to be on the trade market, and Amaro traded a different group of prospects for him instead. (Ironically, one of the players in that deal, Carlos Carrasco, eventually became better than any of the players the Blue Jays were asking for.)

The following offseason, with Halladay set to become a free agent after the 2010 season, the Blue Jays’ asking price lessened. The teams were able to come to a deal, and Halladay was sent to Philadelphia for a package consisting of Travis d’Arnaud, Kyle Drabek, and Michael Taylor. After the trade, Halladay quickly agreed to a below-market three-year extension.

Halladay proceeded to give the Phillies two of the most dominant seasons in team history. It felt like victory was assured every time he went to the mound, and on two separate occasions - including once in the playoffs - he did not allow the opponents to record a hit.

Halladay won a much deserved Cy Young Award in 2010, and if not for an equally great season by Clayton Kerhsaw in 2011, he would have won a second one.

Unfortunately, the end for Halladay came suddenly. After two stellar years with the Phillies, his heavy workload caught up with him. He was injured and ineffective for most of 2012, and an attempted comeback in 2013 was short-lived.

I am aware that while reading this story, many people have assuredly been muttering, “It wasn’t a good move, because he also traded Cliff Lee for a pile of garbage the same day!” I’m not going to tell you the Lee trade was good. I hated it at the time, and it still sucks. However, let’s take a look at the circumstances.

Photo by Jonathan Ernst/Getty Images

While not universally accepted, many people believe the following statements to be true:

1. Negotiations with Lee regarding a contract extension were not going well.
2. Phillies ownership was not crazy about the Phillies paying ace pitcher money to both Halladay and Lee.
3. Ownership wanted Lee traded on the same day as Halladay so that fans wouldn’t get attached to the possibility of having both pitchers on the team.

Forced to choose between the two, Amaro went with the superior pitcher who was willing to sign a cheaper deal. As for the prospects, none of them sent in either direction have amounted to much thus far. (There’s still hope for d’Arnaud, but he can’t seem to stay healthy.)

We shouldn’t allow the Lee trade to keep us from appreciating just how good the Halladay trade was. For the cost of a few replaceable prospects, Amaro was able to not only acquire the best pitcher in baseball, but also retain him at below-market value.