In July of the 2009 Major League Baseball season the name flying around the rumor mill as the one leaving his team via trade was that of Toronto Blue Jays ace pitcher Roy Halladay.

The speculation began when than general manager J.P Ricciardi let the baseball media know that he was willing to deal the 2003 Cy Young Award winner if he was “blown away” with a deal.

Teams all throughout baseball were interested in the workhorse Halladay as they were trying to establish a roster that could push them into the postseason.

Teams such as the Philadelphia Phillies, St.Louis Cardinals, Texas Rangers, Milwaukee Brewers, Boston Red Sox and New York Yankees were all interested suitors.

Ricciardi was close to striking a deal with the Phillies who offered a large package deal consisting of this season’s runner up in the National League Rookie of the Year vote J.A. Happ along with four major prospects.

The deal hit a snag when the Phillies would not part with pitching prospect Kyle Drabek and the deal was axed allowing for the Phillies to send a similar type of deal to the Cleveland Indians for 2008 Cy Young Award winner Cliff Lee.

Halladay finished out his season in a Jays uniform finishing fourth in this season’s race for the American League Cy Young award.

The Blue Jays amidst massive front office changes hired a new team president (Paul Beeston), general manager (Alex Anthopoulos) and reshaped their scouting and development departments while maintaining that they would not speak to the media about the possibility of Roy Halladay being traded this offseason.

Halladay has himself been quoted as saying he will test the free agent market once his contract expires at the end of the 2010 season, as he looks to add himself to the roster of a World Series contender.

This means that the Jays need to deal Halladay while his value is at its peak.

Well guess what folks?

The Roy Halladay trade speculation has re-surfaced yet again.

On Friday, MLB.com’s Carrie Muskat reported that the Blue Jays contacted the Chicago Cubs about a possible deal involving Halladay that would send Chicago Cubs prized shortstop prospect Starlin Castro to the Jays.

Will Alex Anthopoulos' first big move as new GM be the trade of Roy Halladay?

The Cubs, who are financially obligated in a vast manner to Carlos Zambrano, Ryan Dempster, Ted Lilly, Alfonso Soriano, Derrek Lee, Kosuke Fukudome, Aramis Ramirez & Milton Bradley may not have the necessary payroll flexibility to acquire Halladay, unless the Jays can take the large contract of the troubled Bradley (owed $21 million over the next two seasons) in the deal.

The Jays who are going in the direction of a rebuild may not want the disruptive nature or aging body of Bradley within the organization but the deal is still a possible one.

When contacted about the deal Alex Anthopoulos stuck to his guns of not discussing any organizational moves ahead of time by saying:

“[I] can’t comment on any trade discussions, rumors or speculation,”

Would the deal make sense for Cubs General Manager Jim Hendry or will another suitor arise in the form of a different Major League Baseball club?

These are just more questions that will need to be answered during the offseason as the Jays prepare for the 2010 season that slowly approaches them.

Based on the direction Alex Anthopoulos has been going, I fully expect a Halladay deal before the 2010 season and if not than, one will be made for sure before the July 31st trade deadline, albeit for much less of a trade package in return for the star pitcher.

In other Jays news, Fox Sports senior baseball writer Ken Rosenthal has written a piece in regards to Alex Anthopoulos and his recent scouting moves within the Blue Jays organization.

The piece can be read here:
http://msn.foxsports.com/mlb/story/10416132/Blue-Jays-bring-in-more-scouts-to-help-fill-roster