Halladay, Lee together even when apart

PHILADELPHIA -- The Best Pitcher in Baseball sat back last month, doing what he's done in way too many autumns -- watching one more World Series go on without him.

But this one was different.

As Roy Halladay watched this World Series, there was a feeling he couldn't drum out of his brain:

It could have been him.

And he's right. It could have, maybe should have. After all, it was supposed to be Roy Halladay who got traded to the Phillies last July, not Cliff Lee. Who didn't know that?

But then things got all crazy in the pre-trade deadline madness, and That Other Guy wound up in Philly, and That Other Guy wound up in the World Series. So there, due to front-office circumstances way beyond his control, was The Best Pitcher in Baseball, watching That Other Guy … and wondering.

"I think you look at that," said Roy Halladay, on a surreal Wednesday in December, "and you always wonder what could have been."

What he couldn't possibly have wondered, though, was what would happen just a few weeks later. What he couldn't possibly have believed was that, on the 16th of December, he'd be the one smiling for the cameras in Philadelphia wearing a Phillies jersey on his back.

And not just any Phillies jersey.

A jersey with the number 34 on it -- Cliff Lee's number 34.

They can't escape each other, apparently, these two Cy Youngs. They've been handed the same trophies. They've shared the same trade rumors. And then, on Wednesday, they were part of the same magnetic baseball force one more time, on the day the Phillies finally did trade for Roy Halladay …

And then dealt away Cliff Lee to Seattle in what us wordsmiths keep calling a "companion deal."

They've never actually played with each other, these two. And now, it seems clear, they never actually will. But they'll always be, well, "companions" now, won't they?

And if Roy Halladay had any doubts about his inextricable connection to That Other Guy, they were certainly erased on the day of his welcome-to-Philadelphia news conference. It was Roy Halladay's day. But if it was his day, how come so much of it was spent talking about the Cy Young who'd just driven off the exit ramp?

"I don't feel like I'm replacing anybody," Halladay said, on the first day he'd ever spent in baseball as anything other than a Blue Jay. "I feel like I've been given the opportunity to go out and do the best job I can. And that's it."

Except that's not it, of course. Can't be it, because people are going to be talking about these two guys for as long as either of them is still getting paid to throw a baseball 60 feet.

And in Philadelphia -- Halladay's new town, Lee's former town -- people are going to be debating for about a century whether the Phillies would have been better off pairing these two rotation behemoths for one electrifying season instead of spinning Lee off to the Great Northwest to accommodate their payroll limitations and their suddenly shrinking prospect inventory.

I think we could have kept [Roy Halladay and Cliff Lee]. But this was a baseball decision for me and our organization and the people who work in this organization, that we could not leave the cupboard bare.

-- Phillies GM Ruben Amaro Jr.

The questions about that decision, and that rationale, kept on coming Wednesday. And GM Ruben Amaro Jr. and team president Dave Montgomery kept on swatting them back, talking about "baseball decisions" and "the future."

Didn't they have to be at least momentarily seduced by the temptation to hang on to both these dominators? "No question, it was tempting," Amaro said. "But my job is to keep this a viable organization for many years, not just for 2010."

Didn't they have to at least kick around the thought of trading somebody else, anybody else, to carve out payroll room and import some prospects? "Yes," Amaro said. "We did."

And there wasn't anyone else who could have helped "replenish" their farm system? "We did not feel so," he said, succinctly.

And then there was the biggest question: Couldn't ownership have looked at this year and decided the chance to have two Cy Youngs on one staff was a special circumstance and bumped up the payroll?

"Sure," Montgomery said. "And then, when we're all standing around here next year and you say, 'What are you going to be able to do to improve your club, and what talent are you going to use to replace [Joe] Blanton?' the reality is that we just felt that … we were tapped to the point where we did not have what we thought was enough [prospects] left in this organization to focus solely on 2010 and ignore the future."

So there you have it. It was about the money, but it wasn't all about the money. They could have worked around the money by unloading Blanton or someone like him. So it was, in Amaro's words, "mostly" about the need to keep the franchise's window of opportunity open for as long as they could.

"I think we could have kept both," the GM said. "But this was a baseball decision for me and our organization and the people who work in this organization, that we could not leave the cupboard bare. If we had just acquired Roy and not moved Lee, we would have been in a position to have lost probably seven of our best 10 prospects in our organization [in the Lee and Halladay deals]. That is not the way to do business in baseball."

They could have saved themselves all this aggravation if they'd just traded for Halladay last July, of course. And just as importantly, they could have saved Roy Halladay a whole month's worth of aggravation.

Back before the trading deadline freed him from that purgatory, he spent an entire month living the hell that comes with being a Living Trade Rumor. And even now, when he looks back on those fun-filled few weeks, he gets the same look on his face you might see on the face of your Uncle Leo when he recalls that week he passed his kidney stone.

"It was hard," Halladay said. "It was real hard. And not only for myself but I think for my family, answering questions. You know, my kids were getting it at school. It's tough. It's where you learn to be careful what you wish for.

"I was definitely relieved," Doc Halladay said, "when the deadline passed and I could kind of move on."

The part that wasn't such a relief, though, was that once that deadline was behind him, he was still in Toronto -- while That Other Guy took his spot on the team Halladay had told just about everyone he wanted to pitch for, the defending champs, a club that held spring training a pop fly away from his backyard.

So not only did he know he was going to have to travel back into the Rumor Central firestorm this winter, but he also had to suspect his chance to become a Phillie had come and gone -- very possibly forever.

"Much as I wanted to be there, I tried to distance myself from it at the time," Halladay said, "and not really get caught up in it one way or the other."

But good luck on that. Over his first six starts after the deadline, he went just 2-4, with a 4.71 ERA, as he struggled to get his focus back on life north of the border. But then the Yankees came to town in the first week of September. Whereupon Roy Halladay mugged them with a nine-strikeout, one-hit shutout. And he was back.

Even as he was closing out the season with a five-win September, though, he still had his eyes on what lay ahead -- and on the team he could have spent those last two months working for.

So he watched with fascination as the Phillies -- ahem, Cliff Lee's Phillies -- rampaged through the postseason. And he thought about what it might have been like to rampage right there with them. Even "dreamed about it," he said.

"I always wondered what could have been," said Roy Halladay. "But I'm happy sitting here right now."

When this offseason began, he never saw that blissful scene coming, however. He figured he'd get traded. But there weren't many places he was going to allow himself to go. Boston and the Bronx were two of them. But he knew the Blue Jays wouldn't trade him to the Yankees and Red Sox, even though they claimed they would.

And the Phillies? How could that happen? They had Cliff Lee.

But by the time the winter meetings started, he had an inkling something was up. And by last weekend, he knew the framework of a trade had been agreed upon. So he headed for Philadelphia on Monday, thinking he was just there to take a physical, having no idea the Cliff Lee part of this equation was a threat to complicate his life one more time.

"Once I found out about all the moving parts, I realized all the things that could have gone wrong," Halladay said. "But luckily, by the time I found out, it was pretty much done."

So, however, was Cliff Lee's time in Philadelphia. That time lasted only three months. But because those three months manufactured so much glory, it means now it will be Philadelphia's turn to spend the next few years wondering what could have been.

Should the Phillies have kept Lee? Should the Phillies have kept both of them? These are questions that will hover over the Roy Halladay era in his new hometown, whether he fully comprehends that or not.

He has been, unquestionably, the best starting pitcher in baseball for the last eight seasons. But that won't stop Philadelphia from measuring him against That Other Guy.

Roy Halladay, however, won't be listening to those questions. And he won't be taking those measurements.

"I won't think about who was here," said The Best Pitcher in Baseball. "I'll think about what's in front of me."

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.