There was actually one other time when a trade involved two pitchers who would go on
to win the Cy. On Dec. 12, 1980, the Cardinals traded future Hall of Famer Rollie Fingers -- whom they had acquired four days earlier from San Diego -- to Milwaukee along with Pete Vukovich and Ted Simmons for David Green, Dave LaPoint, Sixto Lezcano and Lary Sorensen.
Fingers would win the 1981 AL Cy Young with the Brewers after 28 saves, and Vukovich would win it with the Brewers in '82 (18-6). The Cardinals could not complain, because they beat those same Brewers in that classic seven-game World Series in '82.
The first Cy Young was awarded to Dodgers ace Don Newcombe after the 1956 season, and '67 marked the first time it was given to a pitcher from each league. There have been 67 different individual recipients over that time, and Halladay (2003 AL) and Lee ('08 AL) just became the first pair with that pre-existing hardware to go in the same set of trades.
The closest that a Halladay-Lee situation ever came to happening was on June 13, 1997. On that day, in the last gasps of his career, Fernando Valenzuela was traded by the Padres to the Cardinals in a deal that sent Danny Jackson to San Diego. Everyone knows about Fernandomania of 1981, when the lovable lefty rookie from Mexico took the Dodgers to a title and led the NL with 180 strikeouts, winning the Cy. But do you realize how close Jackson also had come to winning a Cy?
Jackson was 23-8 with 15 complete games for Cincinnati in 1988. Unfortunately for him, so was Orel Hershisher. And for the latter, it was a season in which the Bulldog broke Don Drysdale's Major League record for consecutive scoreless innings -- eventually leading the Dodgers to their title. Baseball Writers' Association of America voters went with Hershiser over Jackson -- a landslide with 24 first-place votes to Hershiser and none to Jackson -- so Halladay/Lee stands alone today.
Rick Wise merits a mention after what just happened with Halladay and Lee. Wise was traded three times, and two of those included a future Cy Young winner. The Phillies traded Wise to the Cardinals for Steve Carlton just before 1972 Spring Training, and that season, Lefty went on to win the first of his four Cy Youngs as a Phillies ace. At the end of the '78 Spring Training, Wise was sent to Cleveland as part of a deal that sent eventual '92 AL Cy Young winner
Dennis Eckersley to Boston.
In 1971, future Hall of Famer Gaylord Perry was traded by the Giants to Cleveland for Sudden Sam McDowell. Perry would go on to win a Cy in each league, a year later with the Indians and then in '78 with the Padres. McDowell came close, having won 20 games for the Indians in '70 to finish third in the voting, behind Jim Perry of the Twins and Dave McNally of the Orioles.
Ever heard of Jack Savage? He was definitely not a Cy Young Award winner, making just a handful of Major League appearances. But he has the curious distinction of having been traded in a pair of notable deals that each involved a future or past Cy Young winner.
On Dec. 11, 1987, Savage was traded as part of a three-team deal, going from the Dodgers to the Mets. There were a lot of big names in that deal, and one of them was eventual '89 AL Cy winner Bob Welch, who went from the Dodgers to the A's. On Oct. 16, 1989, Savage was the player to be named, going from the Mets to the Twins in a move that sent '88 AL Cy winner Frank Viola to the Mets.
Doug Drabek's son Kyle, a Minor League right-hander, went from the Phillies to the Blue Jays in the Halladay deal. Alas, dad won his Cy after a pair of trades. He was a player to be named later in a 1984 trade that sent Roy Smalley from the Yankees to the White Sox. After the '86 season, the Yankees traded Drabek along with Logan Easley and Brian Fisher to the Pirates for Pat Clements, Cecilio Guante and Rick Rhoden (who finished fifth in the '86 NL Cy voting, well behind winner Mike Scott, once traded for Danny Heep).
Doug Drabek won the NL Cy in 1990, going 22-6 for the Pirates.
There have been Cy Young winners traded for future Hall of Famers. In 1972, Denny McClain, who won 31 games for the '68 Tigers, was traded to Atlanta for the great Orlando Cepeda. In '82, Mark Davis, who would go on to win the '89 NL Cy for San Diego with that freakish 44-save season, was traded by the Phillies to the Giants in a deal that sent Joe Morgan to the Phillies.
You might eventually throw the August 1992 David Cone deal into that mix. He helped the Blue Jays to their first title that fall, and in '94, he won the AL Cy with the Royals. Coming from Toronto to the Mets in that '92 trade was Jeff Kent, who is regarded as a strong possibility for Cooperstown after his five-year wait for eligibility is up.
One final mention must be given for the historic 17-player swap that happened after the 1954 season. It is fabled not only for the volume of personnel that was moved, but also for two pitchers and what would become of them later as Yankees. Bob Turley was dealt from Baltimore to the Bronx Bombers and in '58, he would win the AL Cy Young. One of the players to be named later along with Turley was a pitcher named Don Larsen, who in '56 would throw the only perfect game in the history of the World Series.