To some extent, the Yankees failed in both pursuits; Lee, of course, became a Phillie, and Jeter's contract negotiations, although successfully completed, were longer and messier than anyone could have imagined.
This year, there is peace in Yankeeland; CC Sabathia's opt-out situation was handled neatly and without bloodshed, and virtually the entire starting lineup is returning intact.
But the choices that are left to be made are anything but easy.
The Yankees need starting pitching, and there are about a half-dozen starting pitchers available, or soon to be available, on the free-agent market.
And one is a wild card: Yu Darvish.
That is Hal Steinbrenner's problem this winter, and Brian Cashman's, and the Yankees' staff of scouting and player personnel types.
Do they play it safe and go with one of the known commodities?
Or do they roll the dice on the only one who has the chance of being either a spectacular success or a colossal bust?
Assuming he enters the complex and costly posting process necessary for a player to go from the Nippon Baseball League to the major leagues, Darvish's presence in the free agent market this winter greatly complicates the Yankees' thought processes.
It is not difficult to predict what Wilson, Buehrle or Jackson -- and to a lesser extent because of his injury history, Oswalt -- would do as Yankees.
But it is nearly impossible to guess what Darvish would become.
It is not a question that can be answered strictly with numbers, or through the powers of observation, or some kind of gut feeling.
It is basically a very expensive educated guess.
Because as Cashman has pointed out, painfully and in some detail, the history of highly-touted Japanese pitchers is not a happy one, and the problem lies in the difficulty in determining how their performance in the very different environment of Japanese baseball translates to the major leagues.
Differences in the height of the pitcher's mound, in the ability of the batters faced, in the style of ball played and the approach to hitting, in the dimensions of the ballparks and in the composition of the baseball itself all factor into it, and the only way to be sure if a guy who pitched as well as Darvish did in Japan can pitch nearly as well over here is to throw him out there and hope.
Darvish's numbers through his seven seasons with the Nippon Ham Fighters are eye-popping: 93-38, an ERA below 2.00 for the past five seasons, and 1,250 strikeouts in 1,268-2/3 innings.
They are not just better than the stats of Igawa, Hideki Irabu, Daisuke Matsuzaka and Hiroki Kuroda, all of whom came over as highly-touted and highly-paid prospects with varying degrees of success, they are much better.
Much, much better.
And over the past two seasons, Darvish has raised his game to another level: In 2010, he went 12-8 with a 1.78 ERA and 222 K's in 202 innings, and in 2011 he went 18-6, 1.44, with 276 K's in 232 innings. He is said to have six pitches, including a 97-mph fastball, a two-seamer, a slurve, a cutter, a curve, a splitter and a changeup.
On paper, a very tempting prospect indeed.
But no pitcher came to the U.S. more highly-touted than Dice-K. It cost the Red Sox more than $100 million to bring Matsuzaka and his "gyroball" to the U.S., including a record $51 million posting fee. In return, they got a pitcher who was a disappointment despite a 46-27 record in five seasons. They have yet to see him throw a gyroball. And now Dice-K will be out until the middle of next season after Tommy John surgery.
Is it worth it to the Yankees to risk the kind of money it will take to fit Darvish for pinstripes for that kind of performance? A half-dozen teams, including the Yankees, submitted blind bids in the posting process for Dice-K. That many will probably bid on Darvish, too. Will the Yankees even bother to bid? Should they?
"We've had some failures," Cashman acknowledged on Tuesday. "We've obviously signed some Japanese players and failed. We haven't had a successful Japanese pitcher, but it doesn't mean we won't have one. We'll keep working at it."
On Wednesday, Hal Steinbrenner said that the Yankees' poor track record with Japanese pitchers would not necessarily deter them from pursuing Darvish if he makes himself available.
"Every person's different, every player's different," he said. "We're going to look at every single one. We're going to look at every single option and we're going to analyze it, whether it's go or no go. We look at each person as an individual, each player. That's not going to affect anything, at least not for me."
But he admitted that assessing the potential of players from other leagues is a bit of a crapshoot, something like trying to handicap how a horse will run in a six-furlong race over the inner dirt track at Aqueduct in February after having run nothing previously but distance races over a synthetic surface on the West Coast.
You just don't know what he's really got until the gates open.
"Look, it's difficult when you don't have as much film on a player to watch and you don't have as many scouts who've laid eyes on that player before, there's no doubt it's difficult," Steinbrenner said. "But I had never heard of El Duque (Orlando Hernandez) till he came over here, and there have certainly been players who have come out of those countries and been great. But there's just less intel to rely on and there's less to go on. So I do have to heavily rely on our scouting and our player development people, particularly when it comes to young kids in foreign countries."
The Yankees, of course, always claim to have limited interest -- and even more laughably, limited dollars -- at this time of the season, and then always seem to be able to find what they need once they determine who they want.
So it's not so much a matter of money as it is a question of value.
They know that at his very best, Wilson will give them 15-16 wins, an ERA in the mid-3.00s, and quite possibly, a lousy October (he is 1-5 with a 4.82 ERA in the postseason). They know they can count on Buehrle to give them 200 innings a year, win 13-16 games (he won 19 in 2002) and make 30-plus steady if unspectacular starts. They know that if Oswalt is healthy, he can be brilliant, but over the past few seasons, he has rarely been healthy.
None of them is perfect, but each in his own way is predictable.
Darvish, however, is something else again.
They know he was great in Japan. They know he will be very expensive in New York.
Anything beyond that is anyone's guess.
And that's what make this offseason, outwardly a lot more tranquil than last offseason, so much more difficult to navigate.