What contending team wouldn’t want Roy Halladay atop its rotation? He has been the best pitcher in the American League over the past nine years and his dominance has continued through 2009. Despite an August hiccup, Halladay still leads the AL in innings pitched, complete games, and strikeout to walks ratio. “He’s got such overpowering stuff,” says his former manager John Gibbons. “That’s what separates him from other guys — his makeup…his mentality.”

As dominant as he is, Halladay has yet to see the postseason. From 1999 through 2007 the Jays finished third in the AL East seven times. The only departures were in 2004, when they finished last, and 2006, when they squeaked past a Red Sox team that collapsed after a five-game sweep by the Yankees. Now that the Rays have arrived, the Jays appear relegated to fourth place, where they finished in 2008 and likely will in 2009. Will Roy Halladay never see the playoffs?

His chance to sign with a contender will come after the 2010 season, when he finally becomes a free agent. He could have tested the market after the 2007 season, when his four-year, $42 million contract was set to expire. Instead he gave the Blue Jays a hometown discount and signed a three-year, $40 million extension in Spring Training 2006. The team had finished two games below .500 in 2005, but had an aggressive off-season, bringing in Troy Glaus, A.J. Burnett, B.J. Ryan, Lyle Overbay, and Bengie Molina via free agency and trade. The Jays made it clear enough that they were serious about contending and that was enough for Halladay to sign on.

The team saw a seven-game improvement and finished second in the AL East, but still missed the Wild Card by eight games. It was the closest Toronto would come to making the postseason during Halladay’s tenure. Since 2006 they’ve lost players to injury and have seen declining production from some of their once-promising players. For the second straight season they’re heading for a fourth place finish, despite having the best record in the American League on May 20. The only way to sustain that over a 162-game season is to assess their talent level and determine when contending is feasible.

Every team has both short- and long-term goals. The long-term goal for every team, obviously, is to field a contender. Short-term goals can vary. For some teams, the short-term goal is the same as the long-term, to contend. Other teams might find such a short-term outlook detrimental to their long-term goals. Consider the Pirates. For years they were unwilling to undergo a true rebuilding process and were left with a roster full of middling talent and no farm system. If the Blue Jays wish to avoid this fate, they should look closely at their situation and realize that to contend in 2010 is unrealistic. It is in their best interests, therefore, to trade Roy Halladay.

The Blue Jays have the unfortunate knowledge of what could have been. The team fielded offers for Halladay in July, but by the 31st had decided no offers met their standard. When teams line up with their offers this winter, the specter of offers past will loom. According to a Bob Elliot source, the Red Sox offered Clay Buchholz, Justin Masterson, Daniel Bard, Michael Bowden, Felix Doubront and Nick Hagadone. Will the Jays get anywhere close to that offer in the winter, when Halladay can impact only one pennant race, rather than the two?

In one sense, Halladay for 1.5 seasons is worth more than Halladay with just one season remaining. But payroll issues strapped a few teams this season. A few teams that were out in July might be back in after clearing payroll. More bidders theoretically leads to a bigger return, but with teams increasingly unwilling to part with prospects, it seems unlikely any team will match the Red Sox offer — it’s hard to believe that the Red Sox made such an offer in the first place. The Jays would do well to get two very good prospects and two or three B+ or B prospects. That should help reload their farm system.

Without Halladay, the Jays can count on another fourth place finish in 2010 — or even fifth if the Orioles rebuilding plan starts to take shape. That doesn’t mean there won’t be bright spots. Ricky Romero, Brett Cecil, and Mark Rzepczynski will enter their sophomore seasons. Shaun Marcum, Jesse Litsch, and maybe Dustin McGowan will return from injury. Maybe Brad Mills will get to flash some of that stuff he showed in the minors, and maybe Zach Stewart, acquired in the Scott Rolen trade, can make an impact. On the offensive side there’s always Adam Lind and Aaron Hill. Travis Snider still shows promise, and should get a chance with a full-time role next season. It might not add up to a playoff contender, but the Jays have the building blocks of something.

Taking a step back for one season wouldn’t do much harm to the current Blue Jays. In 2011 they would still have a number of players in the primes of their careers. Adam Lind will be 27, Aaron Hill will be 29, Ricky Romero will be 26, Brett Cecil will be 24, Marc Rzepczynski will be 25, Shaun Marcum will be 29, and Jesse Litsch will be 26. That’s a fine core of players, all of whom will still be reasonably priced in 2011. As the Jays shed salary, they can use the money to supplement these players with strategic free agent signings and trades.

One contract might impede the Jays as they transition into life without Halladay: Vernon Wells. After an All-Star season in 2006, the Jays signed Wells, who was due to become a free agent after 2007, to a seven-year, $126 million extension. Worse yet, the deal is backloaded, so that Wells will earn $98.5 million from 2010 through 2014 (plus another $8.5 million, the remainder of his signing bonus). Even with Wells producing to the levels he did in 2003, 2006, and 2008, no team would take that contract. The Jays are stuck with it, and Wells has repaid them with two terrible years in which he couldn’t crack a .730 OPS. He did play well in 2008, but missed significant time due to injury.

Because Wells is part of this team for the next five seasons, the Jays can only hope that he starts to produce again. If he doesn’t, they might have an even harder time contending the AL East. They’ll have a significant portion of their payroll dedicated to one mediocre player. This will make it more difficult to sign other players. Not only is there less available payroll, but ownership might think twice before handing out another long-term deal. They’ve been not only burned with Wells, but with Alex Rios. The latter signed a seven-year, $69.835 million contract before the 2008 season, and under-produced for a season and a half before the Jays foisted him on the White Sox after the latter made a waiver claim.

Edwin Encarnacion is another wild card. Also part of the Rolen trade, Encarnacion had three solid seasons with the Reds from 2006 through 2008 before disappointing terribly in 2009. His slide worsened with his move to the Blue Jays. At 26 he’s not anywhere near physical decline. If he can rebound to his 2007 and 2008 levels, he’ll provide the Jays with an adequate third baseman. He’s signed affordably, $4.75 million, for the 2010 season, and will be under the Jays control for the 2011 season before reaching free agency. He could end up being an important piece of that reemerging team.

While things look bleak for the Jays when looking at the standings and their roster, not to mention their farm system, there is plenty of hope for the team. As general manager J.P. Ricciardi noted, his team “can’t bring back the same team and be confident. Obviously for us to contend we have to address some issues.” A return on Halladay would help them begin addressing those issues. The Jays would still have a few kinks to work out, but they have a solid base of both position players and pitchers that can help them contend as early as 2011. That is contingent upon them conceding the 2010 campaign so they can reload. A futile contention effort in 2010 could set them years back.

Joe Pawlikowski covers the Yankees for RiverAveBlues.com.