Trading the ace of your pitching staff can be an imposing task for any general manager in Major League Baseball, let alone one who had taken the reins just weeks earlier.

And it doesn't get more imposing than the ace in question, Roy Halladay, a Cy Young-winning local hero beloved by baseball fans across the city and country.

Thus was the lot inherited by Alex Anthopoulos when he was name general manager of the Toronto Blue Jays in October 2009.

The Jays were an underperforming club that had been consistently finishing behind the New York Yankees and Boston Red Sox, and later the Tampa Bay Rays in the American League East.

And with Halladay requesting to be moved out of town, it appeared that a rocky start was destined for Anthopoulos.

But Anthopoulos wasn't shaken, trading Halladay in December 2009 for three prospects that would be used to build the foundation of an Anthopoulos-era youth movement.

"You can sit and analyze and say, ‘it's Roy Halladay,' and think about how good he is and what he has meant to the organization and the city and country. But the reality is six months from the time that we traded him he was going to be a free agent," Anthopoulos told ctvtoronto.ca in a recent interview.

"Rather than get caught up in the emotion of it, it was important to look from an objective standpoint at what was best for the organization and what makes the most sense."

Anthopoulos, a Montreal native, got his start in baseball with the Montreal Expos in 2000 before making the jump to scouting coordinator with the Toronto Blue Jays in 2003 and eventually moving up to Assistant General Manager.

Anthopoulos was picked to replace J.P. Ricciardi when he was fired in 2009, after several attempts to build a contender failed to earn the Jays a spot in the post-season.

"We had some nice pieces in place but we needed to add on that and supplement that and I think we've done a fairly good job of doing that," he said. "We're certainly not where we want to be just yet, but I think we are further along in the process than we were a year ago."

Despite moving Halladay, who had won 17 games the previous season, and a career-high 22 wins during his 2002 Cy Young-winning season, the Blue Jays improved during the 2010 season.

They won 10 more games than the previous year, finishing with a record of 85-77. But they still couldn't leapfrog the Yankees, Red Sox or Rays.

Anthopoulos, 33, said he realized he couldn't beat the big boys by playing the same game. The Yankees and Red Sox are among the league's biggest spenders, and have proven their ability to buy the players to contend. He was going to have to take chances and calculated moves that could lead to big payoffs in the future.

What followed the Halladay trade was a series of high risk, high reward moves designed to make the club younger and deeper in talent.

"I know that there is a lot of risk to the moves that we make, but that's where the rewards are going to come in," he said. "If we are doing what everyone else is doing, we are probably not going to be able to move forward."

Halladay had already been moved for three prospects. Anthopoulos would repeat the trend several times over the past year, stocking up on talented players at several key positions as stockpiling draft picks. Earlier this month he traded Shawn Marcum, the team's season-opening pitcher, for a Canadian Brett Lawrie, 20-year-old with the confidence of a veteran hitter.

In his first season as general manager, Anthopoulos managed a modest improvement to the team's record, while restocking the club's minor league system.

"The goal is obviously to build an organization that has a chance to compete and win a World Series year in and year out. It's not a one year thing or a two year thing, but where the window never closes," Anthopoulos said.

Buck Martinez has been around the Toronto Blue Jays for most of his career and in almost every way imaginable.

He played catcher for the club in the 1980s and managed the club for a couple of seasons in the 2000s.

Between that, and since, Martinez has followed the club as a broadcaster: During the Jays World Series winning heyday in the early 1990s and again today with Sportsnet, as the club takes uphill strides to build for the future.

The veteran analyst can see a lot of similarities between the two clubs, specifically the density of young talent and the tenacity of the man guiding the ship.

"You can see a lot of qualities in Alex that mirror Pat Gillick," Martinez said, referring to the man who led the Blue Jays to World Series Championships in 1992 and 1993.

"He is a workaholic, he works in private, he doesn't tell you how much he's working and he does things for the betterment of the organization not to build up his name and reputation."

Significant Moves Under Anthopoulos

Oct. 3, 2009 – Anthopoulos named general manager.

Dec. 16, 2009 – Trades Doc Halladay to Philadelphia Phillies for prospects Kyle Drabek, Travis D'Arnaud and Michael Taylor

Dec. 16, 2009 - Michael Taylor traded to Oakland Athletics for Brett Wallace

Dec. 22, 2009 – Brandon League and a minor leaguer traded to Seattle Mariners for pitcher Brandon Morrow

Feb. 2, 2010 – Signed pitcher Kevin Gregg

April 13, 2010 – Signed free agent shortstop Adeiny Hechavarria to a four-year deal

April 13, 2010 – Traded future considerations to San Francisco Giants for outfielder Fred Lewis

July 14, 2010 – Traded Alex Gonzalez to Atlanta Braves for Yunel Escobar and Jo-Jo Reyes

July 29, 2010 – Traded Brett Wallace to Houston Astros for prospect Anthony Gose

Oct. 25, 2010 – Named John Farrell the new manager

Dec. 6, 2010 – Shawn Marcum traded to Milwaukee Brewers for prospect Brett Lawrie