Roger Clemens signed in Toronto before the 1997 season, and had two completely ridiculous seasons, putting up 20 WAR over about 500 innings, striking out 563 of 2005 total batters over those two years, and winning two Cy Youngs. He asked to be traded before the 99 season.
The Jays sent him to the Yankees, for David Wells, Homer Bush and Graeme Lloyd. Clemens stuck around for 4 years, before retirement #1 of 4 or 5.
Bush had a great first season in Toronto, but couldn't seem to stay healthy or good and was released after 2002, giving the Jays 3 WAR over 4 seasons.
Graeme Lloyd pitched one year in Toronto before leaving as a free agent. As compensation for Lloyd leaving, the Jays got Dustin McGowan and Peter Bauer in the 2000 draft. McGowan is still pitching, and showed a ton of potential before injuries sidetracked his career. He got hurt in his age 26 season, and threw 21 big league innings between then and his age 31 season. He eventually left in free agency. Bauer never reached the bigs, and got plucked in a rule 5 draft.
Wells gave two nice seasons and 7.8WAR over 461 innings, before getting traded to the White Sox for Mike Sirotka, Mike Williams, Kevin Beirne, and Brian Simmons in the "Shouldergate" trade:
Quote:
On January 14, 2001, [Sirotka] was traded to the Toronto Blue Jays with Kevin Beirne and Brian Simmons for Matt DeWitt and David Wells in a deal that would infamously become labeled by White Sox General Manager Kenny Williams as "Shouldergate", as Sirotka would never pitch again, labeled "damaged goods" by then-Toronto GM Gord Ash. Ash believed that Williams did not turn over all information pertaining to Sirotka's shoulder. Ash later appealed the trade to MLB Commissioner Bud Selig, but Selig refused to overturn the trade.[1]
The Jays released Sirotka without ever getting a pitch from him.
I'm a 30-year old, die-hard Blue Jays fan, and have been since I could walk. I have literally 0 recollection of Brian Simmons, but he allegedly played 60 games for the Jays in 97, then got non-tendered. Kevin Beirne threw 7 innings before leaving as a free agent. Mike WIlliams doesn't appear to have ever made it past A-ball. All told, the Jays managed to turn 2 seasons of (arguably) peak Clemens in to about 11 WAR, mostly from David Wells, and then turned him in to absolutely nothing, spread over several players and years.