Despite all the talk and all the questions -- creating an exhausting month that wore down the pitcher's patience -- no team presented the Blue Jays with an offer mighty enough to convince them to trade Halladay. The end result has led many to wonder the same thing.
For the next two months, Halladay will continue to be the leader of the Blue Jays' rotation, heading a cast of promising young starters that have the organization believing it can contend in 2010. That goal is more realistic if Halladay is still in the fold and, presumably, he will be unless Toronto is overwhelmed with a trade proposal over the winter.
Beyond that, the Blue Jays need to do everything they can to convince Halladay to stick around. He will be a free agent after next season and has made it known that he wants to wait to see how things play out before considering a contract extension. Toronto pitching coach Brad Arnsberg does not think signing Halladay is an impossible task.
"Going into next year," Arnsberg said, "I think if we can show this horse that we've got a chance of winning here for the next couple years, I don't think you'd have any problem at all re-signing him or signing a long-term deal, if he was assured of that thought process. If he doesn't see that, I would believe that he would probably play his lottery ticket and test the market."
That could be easier said than done.
The Blue Jays trimmed their payroll heading into this season and might see further reduction in that area going into 2010. Operating on a payroll around $80 million or lower would make it difficult to acquire any high-profile free agents this coming winter, and Toronto needs to upgrade its offense in any way it can.
Toronto manager Cito Gaston is quick to point out that the wealth of young pitching in the organization could prove valuable in that regard.
Next season, the Jays will likely see the return of injured pitchers Jesse Litsch and Shaun Marcum, and possibly Dustin McGowan at some point. Add Halladay to that group, as well as youngsters Ricky Romero, Brett Cecil, Marc Rzepczynski and Brad Mills, among others, and suddenly there is a surplus of arms.
"You can move them and trade them for somebody and get some players," Gaston said. "If they pitch well the rest of the season, that means the value of those guys goes up, too. There's different ways of getting players. If you go back and look at the years we won, all those guys on those rosters didn't come from this organization. They came from a lot of other places.
"You might have to do some of those things, as far as moving guys and picking up other players."
Toronto will have a few holes to fill, too.
Among the starting position players, catcher Rod Barajas and shortstop Marco Scutaro will be eligible for free agency this winter. Center fielder Vernon Wells and right fielder Alex Rios have performed below expectations, but the Jays believe they are better players than they have shown. Top prospect Travis Snider was inconsistent as the left fielder earlier this season, but Toronto is hoping he can rebound in 2010 as well.
All of this amounts to a need for more offense.
"We need to add a hitter here, if we can," Gaston said. "You're going to need some things, but it's not all impossible to certainly be in the mix next year and have a run at it. We'll see in the offseason what happens with these guys and then we can go into Spring Training and look at the team and say, 'Hey, we have a run at it,' or, 'We don't have a run at it.'"
This is the crucial part in terms of keeping Halladay around. If he decides to test free agency following next season -- or, if a slow start by the Jays leads the club to once again consider trading the pitcher next July -- Toronto will likely enter more of a rebuilding mode. From what he has seen so far, Halladay does believe the Jays have shown promise.
Is it enough promise to persuade Halladay to remain with Toronto? Time will tell.
"I definitely feel like there's a plan in place," Halladay said recently. "I feel like it's an organization that's trying to move forward, that's trying to get better. From that aspect of it, I think there's a lot to look forward to here. ... I just think I owe it to myself at this point to kind of wait and see and assess the situation when I have to. I do feel like there's a lot of positives here."
Halladay said he did not believe Toronto needed "major changes" to become a contender.
"Major changes? No," Halladay said. "I think the hardest part is obviously the division we're in. The two, three, four teams that you're up against -- two of them being able to go out and get guys when they need them -- I think that's the hardest part. I don't think that there's major changes.
"I think at some point, you have to catch lightning in a bottle and a lot of things have to go right -- kind of like what happened for Tampa [Bay] last year. I think a lot of those pieces are in place. A lot of the future is there. It's just a matter of, 'When will that happen?' and 'When will it all come together?'"
Without Halladay, things would likely take much longer to come together for the Blue Jays.
"It's easier to win with him than to win without him," Wells said. "He's as durable as anybody and you know what he's going to give you when he's on the mound. That's something that, especially with a lot of the young guys that we've had come up, you continue to be able to watch him and the way he works."
With that in mind, Halladay's teammates were thrilled that the pitcher was not moved before Friday's non-waiver Trade Deadline. Losing Halladay would have meant an organizational shift, and it would have been a decision that Arnsberg said would have been "devastating" for the team.
"It would've been tougher to go on in the sense that you've lost the best pitcher in the world," Arnsberg said. "You set the team back, because you've lost an icon-type figure and you've lost just his demeanor -- his personality -- just who Doc is and what he represents for this organization."
For now, the Blue Jays did not lose any of that.
Jordan Bastian is a reporter for MLB.com. This story was not subject to the approval of Major League Baseball or its clubs.