The first of the Phillies' big gambles to win a third World Series has run its course without the ultimate payout.

The Phillies in the offseason between 2009 and 2010 traded three prospects to Toronto and jettisoned pricey starter Cliff Lee to acquire a 33-year-old workhorse desperate to see the postseason. That workhorse was Roy Halladay.

After pitching the last four seasons for the Phillies, Halladay, 36, will retire. As a Blue Jay, no less.

Three questions arise:

1. Was Halladay worth the prospects, and the money, and Lee?

2. Will he be in the Hall of Fame?

3. Should he consider retiring a Phillie?

Answers: Yes, yes and no.

The third one first: Halladay was drafted in the first round by the Jays in 1995, served as the face of that franchise from 2002-09 and collected 148 of his 203 wins in Canada, in a division dominated by the Red Sox and Yankees. Halladay is a Jay.

The second one second: Halladay is the second-best case so far for adjusting the criteria for Hall of Fame pitchers. He won 203 games; only 19 of the 70 Hall of Fame pitchers won fewer. Six of those were primarily relievers. Almost all of the rest either played before 1900 or were voted in by the Veteran's or Old Timer's committees. The three exceptions – Dazzy Vance, Sandy Koufax and Dizzy Dean – were strikeout machines. Vance and Dean won MVP awards.

Halladay evolved into a strikeout pitcher, but, more to the point, he continually evolved as a pitcher. To wit: He developed a changeup in 2010, which helped him log the best of his 16 seasons. In it, Halladay led the majors with 21 wins, more than 250 innings, nine complete games and four shutouts, one of them the second perfect game in Phillies history. He also pitched a no-hitter in his first playoff appearance. Halladay doesn't have the postseason credentials of the best recent argument – Curt Schilling – but Halladay never kept his team from reaching the postseason and he did not quail in those moments.

The first question: Absolutely, Halladay was worth it. Travis D'Arnaud might make it as a big-league catcher, but pitcher Kyle Drabek stays hurt and big outfielder Michael Taylor might be a lost cause. And, well, the Phillies wanted to replenish those prospects and save a little money, so they traded Lee.

The Phillies got cash from Toronto but extended Halladay's contract after the trade. They ultimately spent just under $70 million for 57 wins and 30 losses, including the postseason, but they knew extending Halladay's contract was dangerous. Sure enough, his shoulder gave out in the second year of that deal, his third with the Phils.

Still, he validated the team, and its cruel ballpark.

Lee and Jonathan Papelbon, when they were free agents, had their choice of pitching staffs and safer home fields; still, they chose Philadelphia. Cole Hamels and Kyle Kendrick benefited inestimably from Doc's presence, professionalism and philosophy.

"He helped me understand the game more," Hamels said in a team statement.

"Roy was probably the best influence in my career," Kendrick added.

Like most of the big deals done by general manager Ruben Amaro, Jr. since his ascension – Ryan Howard, Jimmy Rollins, the early returns on Papelbon and Hamels – Halladay's deal wasn't without risk, and did not return full value.

Hardly any deal ever does.

Halladay was worth every penny.