alt text This offseason, the best decision for the Blue Jays will be trading Roy. Halladay’s contract expires after the 2010 season, and it’s very unlikely that he will sign another contract with the Jays. Toronto is in the midst of restructuring, so they should look to compete around 2012. Halladay is the best trading chip the Blue Jays have if they want to add young talented players.

On Friday, Blue Jays president and CEO Paul Beeston told the New York Post that Halladay will not remain in Toronto when his contract expires after the 2010 season. “We would like to sign him. He is an original Blue Jay and we have never had a pitcher as good as him, but he is not inclined to sign with us,” said Beeston. Halladay wants to win, and so do the Jays, though both have different timelines to achieve that goal.

The Blue Jays franchise is not in as complete a mess as some think. Former general manager, J.P. Ricciardi left a solid core of young players behind, like pitchers Ricky Romero, Brett Cecil, and Mark Rzepczynski and hitters Adam Lind, Aaron Hill, and Travis Snider. By trading Halladay this offseason, the Jays could add more young and controllable pieces to their core instead of losing Halladay to free agency and receiving only two compensatory picks in the 2011 First-Year Player Draft.

Since Halladay becomes a free agent after the 2010 season, teams might not be willing to give up a lot of young talent for just one year of Halladay. However, rookie general manager Alex Anthopoulos has stated he would give teams a window to negotiate an extension with Halladay in trade talks, which would definitely guarantee the Blue Jays a more significant return.

Halladay should be a hot commodity this offseason. He had a terrific 2009, as he went 17-10 with a 2.79 ERA, 208 strikeouts, and a 1.13 WHIP spanning over 32 starts and 239 innings, with nine complete games and four shutouts. Halladay is in a class of his own, pitching in the toughest division in baseball, the American League East.

Because Halladay has a no-trade clause, he is most likely to end up on a team that is ready to win. He should join a team that has the payroll flexibility that will allow them to sign Halladay to a contract extension past 2010. On the open market, Halladay could definitely command a five-year contract worth $20-25 million per season. Teams need solid young players and prospects with a tremendous amount of talent to get a deal done. It’s likely that the New York Yankees, Chicago Cubs, Philadelphia Phillies, Boston Red Sox, Los Angeles Dodgers, Los Angeles Angels of Anaheim, Texas Rangers, and the New York Mets will express interest in Halladay. Colorado Rockies could emerge as a dark horse in the trade talks, since Halladay is from the Denver area and the Rockies reached the playoffs two of the last three seasons.

Rumours swirling this past weekend spoke of Blue Jays and Cubs discussing a possible deal for Halladay. The Cubs haven’t won the World Series since 1908, so trading for Roy Halladay would be a start in the right direction. The Cubs have some solid prospects that could interest the Blue Jays: shortstop Starlin Castro, third baseman Josh Vitters, and starting pitchers Jay Jackson, and Andrew Cashner. The problem facing the Cubs at the moment is that they probably will be unable to take on the $15.75 million owed to Halladay in 2010, since they already have several immovable contracts, like outfielders Alfonso Soriano and Milton Bradley.

The New York Yankees have the best chance of putting together an alluring package for Roy Halladay. They have the money to lock up Halladay long term, and most importantly, the best pieces to get a deal completed with Toronto. Plus, the Yankees will do everything in their power to keep Roy Halladay away from the Red Sox. The Yankees could centre a package around one of right-handed pitchers Phil Hughes or Joba Chamberlain, as both would be ready to make a quick impact. The Yankees’ catching prospect Jesus Montero could interest the Jays. The young catcher batted .337 with 17 HR, 70 RBI, and a .951 OPS in 2009 between High-A Tampa and Double-A Trenton. Trading Halladay to a team within the same division should not be an issue, especially if that team has the best offer on the table.

Overall, it will be difficult for Blue Jay fans to face the fact that Roy Halladay’s tenure in Toronto is nearing an end. The 2003 Cy Young Award winner has meant a lot to this franchise and will go down as one of the greatest players to wear a Blue Jay uniform. The Blue Jays are unlikely to make a run for the postseason in 2010, but trading Roy Halladay is the best way to build the team into a perennial contender over the long run.