If so, the memories of his 17-week Texas Rangers career will be a conflicted one. So good and yet, so 0-2.
Lee started this World Series against the San Francisco Giants with a loss and ended it with one. As prop bets go, you would have gotten Bengie Molina-sized odds on the chances of Lee taking the L train twice in six nights.
He wasn't the best pitcher in this Series. That was San Fran's Tim Lincecum. He wasn't the second best (the Giants' Matt Cain). Or third best (SF's Madison Bumgarner). I'm not even sure he was fourth best (Texas Colby Lewis?).
Instead, he was on the wrong end of half the wins the Giants needed to close out this Series on Monday night at Rangers Ballpark in Arlington. Not only did he give up the deciding three-run dinger to Edgar Renteria with two out in the top of the seventh, but he was out-dueled by a guy who arrived at the stadium wearing a bow tie. It was like getting beat by George Will.
Actually, Lincecum had electric stuff. The Dallas-area power grid could have run off it for weeks. Lee was good (seven innings, six hits, six strikeouts, those three earned runs), but Lincecum was, well, freakishly good.
"It was a classic pitchers' duel -- down to that home run," Lee said. "Nobody in this room is more disappointed than I am."
Lee spoke in measured, even tones, but his eyes said otherwise. They were red and borderline misty. Anybody who thinks these losses didn't leave more than a flesh wound doesn't know Lee.
"If I could go back in time and make a different pitch, I would," Lee said. "But you can't do that."
It was a cutter, by the way. A cutter that didn't cut. It found the fat part of the plate, then the fat part of Renteria's bat and then the left-field seats.
Why he didn't go ahead and walk Renteria with the count at 2-0 is a question that will make the sports-talk rounds. With runners on second and third and first base open, Lee could have pitched around Renteria and taken his chances against the little-used Aaron Rowand.
"I don't really want to load the bases right there," Lee said.
So he threw the cutter and Renteria hit the dinger that gave the Giants their first world championship since 1954.
Rowand flew out to right to end the inning.
That's how it goes. Without Lee, the Rangers probably wouldn't have defeated the Tampa Bay Rays in the American League Division Series or perhaps the Yankees in the American League Championship Series. He was the rotation's rock.
But now the Rangers have to beat the Yankees again. They outflanked the Yankees in the July 9 trade that brought Lee to Texas. They outscored and outpitched them in the ALCS. Can they out-money-whip them?
Lee, 32, became a free agent as the Giants were dousing each other with bubbly. This weekend he can begin entertaining offers from all teams.
"This is the first time I've been a free agent," he said. "I'm going to see what that's all about. I know I enjoyed it here. I'm not ruling out the possibility of coming back, but I've got to play things out and see how it goes. I know this was a great group of guys, a lot of fun and I would love to be a part of it next year, but like I say, there's so many things that can happen, you never know."
Lee's priority list isn't all that unusual for high-profile free agents:
• The traditional "What's best for my family" was mentioned first.
• Playing for a winning team was next.
He didn't have to say anything about money. It's a given Lee is going to command something in the range of $20 million per season for five or six years. And nobody in the Rangers' clubhouse will blame him if he goes elsewhere to get it.
"I think any guy here would tell you, 'God bless him, go get what you can,"' Rangers outfielder Jeff Francoeur said. "At the same time, it comes down to what you're comfortable with, what's enough money. It depends how bad, obviously, New York wants him and how bad they have to have him. And you can see how bad we want him here."
Chuck Greenberg, the Rangers' managing general partner, says all the right things: He wants to re-sign Lee the Texas roster is built for years of champagne/ginger ale celebrations the franchise is flush. And I believe him.
"We think we're well-positioned for the future," he said.
But the Rangers aren't Yankees flush. Nobody is. The Steinbrenners can do the backstroke in their revenue streams. They give seminars to the U.S. Treasury Department on how to print money.
I really don't know what's going to happen or where I'm going to be. I want to be on a winning team. I want to be on a team, if not this team, like this team.
”-- Cliff Lee
Let's face it: the Yankees are baseball's Death Star. Their checkbook blots out the sun. They can offer Lee the most dollars and the most contract years. Most free agents are powerless against The Force. (Hal Steinbrenner: "Cliff, I am your faaaather.")
"Whenever there's an attractive player, the Yankees are part of the equation," Greenberg said. "So that's just part of the reality of the industry."
Lee is a Cy Young winner, a three-time All-Star and a left-hander. Good things to have on a roster. But he's also 32. If you're the Rangers, do you want to commit at least $100 million and five years to a starting pitcher in his early 30s?
If it's me, I say no. And not just no to Lee, but no to any pitcher with a similar birth certificate. Love the guy -- just not for that money and those years.
The Rangers are his fourth team in two years. He can stay and become Lotto rich and beloved. Or he can go to the Yankees and become Lotto rich squared and maybe beloved. He'd join a rotation of CC Sabathia, Phil Hughes, Andy Pettitte (who is a decent bet to re-up for a one-year deal) and A.J. Burnett.
"I really don't know what's going to happen or where I'm going to be," Lee said. "I want to be on a winning team. I want to be on a team, if not this team, like this team. The most fun I've had playing the game [was] with these guys. It's been a good ride. I've enjoyed every single second of it."
Every second of it, except the ending.
Gene Wojciechowski is the senior national columnist for ESPN.com. You can contact him at email@example.com. Hear Gene's podcasts and ESPN Radio appearances by clicking here.