Pressure building on Amaro, Ricciardi

It isn't just a baseball trade. Not anymore.

It isn't even just about Roy Halladay. Not anymore.

This is now about Toronto's J.P. Ricciardi, a general manager who may not be able to "win" whether he makes this trade or not.

And this is now about Philadelphia's Ruben Amaro Jr., a man facing massive public pressure to make a legacy-defining deal -- which would just happen to be his first major deal as a general manager.

Ask yourself this: Would you want to be either of these men this week?

They're playing tug-o'-war on a once-in-a-generation pitcher -- the face of one franchise, a season-changing figure for the other.

They are trying their best to do the right thing while operating in the middle of an unbearable crucible. Their fans are screaming. Their players are lobbying. Their owners are watching. Their tempers are flaring.

And they both know there could be a dangerous cost if they do the wrong thing -- even if it's just what their fan bases perceive as the wrong thing.

So these are two general managers under insane pressure. But which one is under more pressure to make this trade? Which one has to get this right -- or else?

"You know, that's a very interesting question," said one of the veteran baseball men we surveyed. "And I'm not sure about the answer."

Well, we're not so sure, either. So let's think this through.

The heat on Amaro

"I wouldn't want to be in Ruben's spot right now," said one longtime baseball man who once played for the Phillies. "If he doesn't make this deal, the wrath of Philadelphia is going to come right down on him."

Hoo boy. Will it ever. And when the wrath of Philadelphia comes down on anyone in sports, it's not a fun place to be. Ask Scott Rolen. Ask Ed Wade. Ask Rich Kotite.

But if this Halladay deal never gets done, the wrath of Philadelphia in four days could be a lovefest compared to the wrath of Philadelphia in four months. And here's why:

For the fans of Philadelphia, Halladay is more than just a trade rumor now. He has become an obsession -- for an entire metropolitan area.

For two weeks, he has been the only sports topic in town. On the airwaves. On the Jersey beaches. On the subways. At every restaurant table in town.

So if Aug. 1 rolls around and Halladay isn't a Phillie, that won't be an issue for only a day or two. It will be an issue that hangs over this GM and his front office for the rest of this season. Maybe the rest of their time in Philadelphia.

And if the Phillies get bounced out of the postseason at any point short of the parade floats after not dealing for the pitcher the city decided it had to have, it won't be just their season that will be over.

Even worse, the yearlong love affair between town and team will be over.

And the guy who will get blamed is the first-year GM who didn't make the Big Deal -- unless he can do some awfully convincing spin-doctoring.

"If this were Pat Gillick, he might be able to get away with this," one veteran baseball executive said. "Gillick has the stature. Gillick has the rings. So if he didn't get this done and then made some little deal instead, he'd survive. But knowing that town, I really don't know whether Ruben could survive if he doesn't make this trade."

Another longtime baseball man said, "You know, in some ways, Ruben walked into a great situation there, because he inherited a good club, with a good manager and a good farm system. But in other ways, it's a bad situation -- because he's in a situation where people could run him out of town if he doesn't make this deal."

So which GM is under more pressure? It almost has to be Amaro. Doesn't it? Then again …

The heat on Ricciardi

Now we come to the man on the other side of the bargaining table.

This is no easy time to be J.P. Ricciardi, either.

When you put a package like Roy Halladay on your shelves, you have no choice but to price him as if you're Neiman Marcus. This is no time to open a T.J. Maxx.

So for now, Ricciardi is doing exactly what he has to do -- set the bar higher than Mount Everest. The question is: What happens if no one is willing to pay those prices? Then what? Does he have to trade this man or not?

"Here's his problem," said an official of one American League team. "He's so far down this road now, I think he has to deal the guy this week. Their fan base is getting crazy. Their players are wondering what's going on. Halladay can't be too happy. It's turning into a circus. Roy Halladay is more popular than the Blue Jays organization. If people feel like you're jerking him around, then you've got even a bigger problem."

Of course, if the Blue Jays don't trade him this week, they'll have a different explanation. They'll say this man was too special to deal for what they were offered. They'll say they'll keep him and try to win with him next year. And as popular as Halladay is, that spin just might work.

"People talk about the pressure to make a deal, but I think there's actually more pressure the other way," another AL executive said. "I think the pressure from fans, and even from ownership, is actually: 'Don't do this. This is The Guy. We want him to stay.' So the pressure is not to do it. If you do anything less than make a great trade, the fan base might go crazy."

But another veteran baseball man disagreed, saying, "What are the chances of Halladay staying there after next year? They're zero. And you know those two draft picks they'd get if he left? How often do those two picks turn into stars? Not real often. So J.P. knows that if he's going to get impact players for Roy Halladay, he has to deal him."

And if Ricciardi is to get more than one impact player back, he can't wait to deal him any old time. That trade has to come in the next four days.

"He has to deal him now if he's going to get the kind of package he thinks he can get," one former GM said. "You know damn well this guy isn't getting through waivers [after Friday]. And if he gets to the winter, now he's just a rent-a-player."

So that's the pressure-packed dilemma facing Ricciardi this week.

If he doesn't trade Halladay, he might make his fans happy -- but he'll lose his chance to make a truly epic deal.

And if he does trade Halladay, he'll get the max return -- but it could vacuum all the life out of a franchise that hasn't played a postseason game since Joe Carter finished rounding the bases in 1993.

Talk about your classic lose-lose situation. It doesn't get much more lose-lose than this.

So how can any GM possibly be under more pressure than Ricciardi this week?

Where's it all leading?

OK, now that we've broken down the forces hammering down on each side, which of these two has to make this trade?

Our bet is: both of them.

"The truth is, they're going to have a hard time keeping him," an official of one team said of the Blue Jays. "They probably have to trade him. What they don't have to do is trade him now.

How many times do you get a chance to repeat? Well, [the Phillies'] chance to repeat, to me, depends on whether they can get Roy Halladay. Heck, if they get him, they've got a chance to three-peat.

-- A veteran baseball executive

"If I were J.P., I'd ratchet up the pressure on everybody right to the [deadline], because if you're trading Roy Halladay, there's no downside to that. The only way his value is going down is if he gets hurt. That's the only way. So for all I know, J.P. may already be satisfied with the offer he's gotten [from the Phillies]. But why would he take it today? If he waits, they may get scared and throw one more guy in, or move one guy out and move a better guy in."

The Phillies, on the other hand, may have every reason to back off, tell the world the Blue Jays are making unreasonable demands and make a run at Cliff Lee. But in truth, Halladay is the guy they want and the guy their fans want.

"How many times do you get a chance to repeat?" asked one veteran baseball executive this week. "Well, their chance to repeat, to me, depends on whether they can get Roy Halladay. Heck, if they get him, they've got a chance to three-peat."

"You're only in the sunlight so long," said an official of another club. "When you have a team like they have, you have to give that team a chance to win again. And one thing about Roy Halladay: He's the surest bet they could ever find for their situation. And they could probably even re-sign him because he lives right there [near their spring training home in Clearwater, Fla.]. I don't see how they could not do this."

Hey, it all sounds logical to us. But then again, we're not the ones sitting under the heat lamps in the two general managers' offices. Are we?

Jayson Stark is a senior writer for ESPN.com. His new book, "Worth The Wait: Tales of the 2008 Phillies," was published by Triumph Books and is available in bookstores and online. Click here to order a copy.