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Halladay knew he had to demand a trade from Jays if he wanted to win

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By the time Alex Anthopoulos was setting his roots as Blue Jays general manager, it was also time to set free one of the best starting pitchers in franchise history.

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In sportswriter Todd Zolecki’s thorough biography on Roy Halladay, the Toronto years are well-documented. And by the time Anthopoulos took over from J.P. Ricciardi in October 2009, Doc was ready to move on.

Though he didn’t have much choice in the matter, dealing Halladay was one of the Montreal native’s biggest regrets in that it denied Toronto fans of the biggest accomplishments of the all-star pitcher’s career.

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“The shame of it for me is when you think of Roy Halladay and his greatest moments you think of the playoffs with the Phillies,” Anthopoulos says in Doc: The Life of Roy Halladay. “It wasn’t his fault. We never got those guys to that stage.”

Complicating matters was the fact that Halladay had a no-trade clause in his contract, meaning he had to approve any deal Anthopoulos was able to engineer.

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“I didn’t begrudge him that he had it, but from there I’ve never given out a no-trade clause,'” Anthopoulos said.

“We were caught in a tough spot. He made it very clear: ‘I’m leaving. There’s nothing you can do to make me stay. You can offer me all the money in the world. I need to win. I want to win.'”

Halladay’s wife Brandy said her husband recognized the peak years of his career were winding down and, with no realistic post-season prospects for the Jays, it was time to move on, despite the family’s affinity for Canada’s biggest city.

“Roy was so loyal to a fault,” Brandy Halladay relates in the book. “We renewed contracts there multiple times. We loved Toronto so much. He just wanted a chance to compete. Three different contracts they signed, it was: ‘We’re going to rebuild. We’re going to rebuild. We’re starting over, we want you to be a big part of it.’

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“It just never quite happened. You only have so much time to make things happen and be relevant in this game. He wanted a chance to win.”

The frustration was not limited to the Halladays as fellow drafted-and-developed Jays starting pitcher Chris Carpenter noted.

“It was a lot of change,” Carpenter told Zolecki. “There was a change in ownership. There was a change in general managers. It was so much change that we didn’t know what the hell was going on — except that they expected us to beat the Yankees.”

As for the issue of being inducted into Cooperstown last summer without either a Jays or Phillies cap, Brandy said the family was confident it made the correct decision.

“Everybody wants to pop in like they have the right to an opinion or whatever, which is fine,” Brandy tells Zolecki. “But I know he would have never chosen …. I talked to the boys (the Halladay’s two sons) and they absolutely said no … no logo.”

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