The Blue Jays needed more time and Halladay's biological baseball clock was ticking. Winning a World Series is now the pitcher's main focus, and Toronto was not in a position to make any promises. That is why Halladay approved a trade to the Phillies -- to continue chasing his dreams of champagne and championships.
"They needed to start over," Halladay said of the Jays during his news conference in Philadelphia on Wednesday. "And I wanted to continue that pursuit."
In October, Halladay watched the Phillies -- the club that attempted to trade for him last July -- reach their second consecutive World Series. He saw left-hander Cliff Lee, who was acquired in a deal with the Indians after talks about Halladay fell apart, take the hill for Philadelphia in a Fall Classic eventually won by the Yankees.
Had the Jays pulled the trigger on a trade over the summer, that could have been Halladay toeing the rubber in the World Series. He couldn't help but wonder what might have been.
"I can't lie, I did," Halladay said. "I had quite a few dreams about it, too."
Approving the trade to the Phillies -- setting the table for a complicated series of deals involving four teams and nine players -- was an easy decision on Halladay's part. As part of the blockbuster deal, Lee was dealt to Seattle and prospects were shipped to Toronto, Philadelphia and Oakland. In the end, the Jays received a trio of former first-round picks in Kyle Drabek, Brett Wallace and Travis d'Arnaud.
Halladay also agreed to a three-year contract extension with Philadelphia, which will pay him $60 million over 2011-13 and included a vesting option worth $20 million for 2014. Halladay, who was eligible for free agency next winter, took less money than he could have made on the open market. That was the same kind of loyalty he displayed in his time with the Jays.
Twice, Halladay inked extensions with the Blue Jays that were worth less than market value. Above everything else, Halladay's top priority is winning. Individually, he showed that by compiling 148 wins and 49 complete games over a 12-year span with Toronto, winning at least 16 games in a season six times in the past eight years and earning the American League Cy Young Award in 2003.
Halladay would likely trade all of those accomplishments for a ring.
"This is a dream come true," Halladay said. "The longer you play in your career, the more important [winning] becomes. I've been able to establish myself, achieve things. The more I play, the more I realize how important that is for me. To see a team do it in back-to-back years and have that success says a lot about the players in the clubhouse and people that are putting the team together.
"It's not an accident. I want to be a part of that."
That being said, Halladay -- originally selected by the Blue Jays in the first round of the 1995 First-Year Player Draft -- hoped to be a part of something special in Toronto.
"I don't think Roy Halladay wanted to leave Toronto," said Blue Jays president and CEO Paul Beeston. "I think he's made that quite clear. On the other hand, what would trump that would be a chance to play for a contender."
As important as being on a perennial contender was for Halladay, he also left the decision up to his family. By waiving his no-trade clause to approve the deal to the Phillies, the Halladays don't have to leave their home in Florida. Philadelphia's Spring Training site in Clearwater, Fla., is only a short drive from their home.
Halladay did not make the call on his own, though. In fact, his 9-year-old son, Braden, also played a role in the decision.
"It's such a family decision," Halladay's wife, Brandy, told the Philadelphia Daily News. "We were sitting with our agent who is like family and we said, 'OK, we've got to decide what to do.' So I grabbed my phone and I called my 9-year-old. And I said Braden, 'This is the situation. I'm going to put you on the phone and you guys decide if this is what we're going to take.'
"So our 9-year-old made the call. He made the decision. I know that sounds utterly ridiculous, but we're a tight family. If the kids weren't happy ..."
Who knows? Maybe Halladay would have remained with the Jays.
With Philadelphia, Halladay will wear No. 34 after donning No. 32 throughout his time in Toronto. Changing his uniform number was hardly a big deal for Halladay.
"As long as it says 'Phillies' on the front, I don't care what's on the back," Halladay said.
Down the road, it is likely that Halladay's No. 32 will be placed on the Blue Jays' Level of Excellence, honoring him as one of the greatest players to suit up for Toronto. During the upcoming season, when the Phillies head to Toronto for a series in June, the Jays will probably take time to honor him in some way as well.
Halladay -- rarely one to show much emotion -- admitted at the end of the season that walking off the mound in Toronto for the last time was a special moment. As he headed to the dugout, Halladay raised his cap high in the air after finishing off a shutout victory over the Mariners.
The fans inside Rogers Centre rose to their feet and joined together, chanting, "Thank you, Roy!"
"It's been a big part of my life and something I'll never forget," Halladay said of his time with the Blue Jays. "I enjoyed my time there. I'm also extremely excited about a new chapter."
Jordan Bastian is a reporter for MLB.com. This story was not subject to the approval of Major League Baseball or its clubs.