1999 Clemens Trade to Yankees

February 18, 1999. Pitchers and catchers had barely dropped their bags in Florida when the news broke: the New York Yankees had traded for Roger Clemens, the best pitcher of his generation, sending David Wells, Homer Bush, and Graeme Lloyd to Toronto to get him. Nine months earlier, Wells had thrown a perfect game; four months before that trade, he'd won ALCS MVP on a team that just swept the World Series. Now he was gone, shipped out for a 36-year-old righty who'd spent the better part of a decade trying to beat the Yankees, not join them. (The Rocket, as everyone called him, was used to being the enemy in these parts.) Nobody in the Bronx had ever seen a trade quite like it.

Clemens Wanted Out of Toronto

Clemens didn't leave Boston on his own terms. After the 1996 season, Red Sox GM Dan Duquette let him walk as a free agent, saying the club had hoped to keep him around "during the twilight of his career." (That quote followed Duquette around for the rest of his life, and for good reason.) Clemens signed a four-year, $40 million deal with the Blue Jays and spent the next two seasons making Duquette look like an idiot -- back-to-back pitching Triple Crowns, back-to-back Cy Youngs, 41-13 combined. In 1997 he became the first AL pitcher to lead the league in wins, ERA, and strikeouts in the same season since Hal Newhouser in 1945. He did it again in 1998.

None of it mattered in the standings. Toronto finished last in the AL East in 1997 and a distant third in 1998, nowhere near the 114-win Yankees. By December 1998, Clemens had seen enough. He told the Blue Jays he wanted to be traded, frustrated that ownership wouldn't spend to build a real contender around him. A player can't technically demand a trade under the rules of the sport, so the whole thing got handled quietly -- Clemens reportedly walked the formal request back in January, but the conversations never stopped. Two months later, on the first day of spring training, the deal got done anyway.

The Cost Was a Fan Favorite

Here's the part that made Yankees fans wince. Wells wasn't just a good pitcher the front office was willing to move. He'd thrown the 15th perfect game in MLB history on May 17, 1998 -- 120 pitches, 11 strikeouts, a 4-0 win over Minnesota in front of 49,820 people at the Stadium. He'd gone 2-0 with a 2.87 ERA and 18 strikeouts across 15.2 innings against Cleveland that October and taken home ALCS MVP. He was a San Diego kid who grew up idolizing Babe Ruth so hard he'd once dropped $35,000 on an authentic Ruth cap and worn it to the mound. (Manager Joe Torre made him take it off after one inning. Wells kept the hat anyway.) Trading him four months after that October run felt, to a lot of fans, like trading away the guy who'd just handed you the parade.

Graeme Lloyd went too, and he wasn't nothing -- the towering Australian lefty had been Torre's postseason security blanket, stranding five inherited runners against Atlanta's power trio in the '96 World Series and posting a 1.67 ERA in 1998. Two rings, gone in the same trade. Homer Bush, a speedy infielder buried behind Chuck Knoblauch on the depth chart, rounded out the deal -- he'd get his shot in Toronto and take it, hitting .320 with 69 runs and 32 stolen bases as an everyday second baseman in 1999.

Not the Rivalry You'd Expect

The instinct is to frame this as Clemens finally settling a postseason grudge against the Yankees. That's not actually what happened, because it couldn't have -- the Red Sox and Yankees had never met in the postseason before 1999. What Clemens brought with him instead was over a decade of regular-season AL East warfare from his Boston days, the kind fans of both teams remember as "beanball wars," not October drama. The real irony showed up later that year: Clemens's trade set up the first-ever Red Sox-Yankees playoff series in history, and he was suddenly on the other side of it.

What the Trade Actually Bought

Clemens's first year in pinstripes wasn't the dominant show Toronto had gotten used to -- 14-10, 4.60 ERA, more mortal than anyone expected. The 1999 Yankees didn't need him to be perfect. They went 98-64, and in October, Clemens gave them exactly the kind of start a front office trades away a fan favorite to get: 7.2 innings, one run, in the Game 4 clincher against Atlanta that sealed the sweep. Ring number one arrived that same year.

But that October delivered a twist nobody saw coming back in February. The Yankees and Red Sox met in the ALCS for the first time ever, and Pedro Martinez torched Clemens in Game 3 at Fenway -- two innings, six hits, five runs, gone before he could do any real damage. As he walked off the mound, the crowd that used to chant his name chanted "Where is Rog-er?" and told him to go have another donut. Boston won that game 13-1. It was the Yankees' only loss of an otherwise 11-1 postseason run, and they still closed out the series in five.

The Verdict Nobody Saw Coming

Wells actually outpitched Clemens over the next two seasons -- 37-18 in Toronto against Clemens's 27-18 in the Bronx. That's a freakin' rough stat to explain if you're the Yankees front office grading this trade on paper. But nobody in the Bronx cares about spreadsheets in February. Clemens picked up two championship rings in his first two years in pinstripes. Wells picked up zero in Toronto, got flipped to the White Sox after 2000, and came right back to the Yankees in 2002 like the whole detour never happened.

Frequently Asked Questions

When was Roger Clemens traded to the Yankees?

February 18, 1999, the day pitchers and catchers reported to spring training. The Blue Jays sent Clemens to New York for David Wells, Homer Bush, and Graeme Lloyd.

Why did the Blue Jays trade Roger Clemens?

Clemens asked to be traded in December 1998, frustrated that Toronto's front office wouldn't spend to build a contender around him despite his back-to-back Cy Young seasons in 1997 and 1998. The Blue Jays finished well out of playoff contention both years.

Why did the Yankees trade David Wells right after his perfect game?

The Yankees valued Clemens, the best pitcher in baseball at the time, more than Wells, even though Wells had thrown a perfect game and won ALCS MVP just four months earlier. It was a straight upgrade in talent on paper, even if it cost the club a genuine fan favorite.

Did Roger Clemens have a history with the Yankees before the trade?

Not in the postseason -- the Red Sox and Yankees had never actually met in the playoffs before 1999. Clemens did have over a decade of heated regular-season AL East rivalry with New York from his 1984-1996 run with Boston.

Who won the trade, the Yankees or the Blue Jays?

Statistically, Wells outpitched Clemens over the following two seasons, going 37-18 in Toronto to Clemens's 27-18 in New York. But Clemens won two World Series titles with the Yankees in that span, while Wells's Blue Jays missed the playoffs both years -- so the ring column settles the argument the stat line can't.

Two rings in two years will cover for a lot of uneven regular seasons. Ask George Steinbrenner if he'd make that trade again. He'd have made it twice.