1947: Max Bentley and Cy Thomas from Chicago to Toronto for Gus Bodnar, Bud Poile, Gaye Stewart, Ernie Dickens, and Bob Goldham. 28-year-old two-time Ross and one-time Hart winner and a throw-in for five solid players.
1964: Andy Bathgate and Don McKenney from New York to Toronto for Dick Duff, Bob Nevin, Arnie Brown, Bill Collins, and Rod Seiling. Future HOF'er and a veteran defensive forward for several younger guys, all of whom went on to have long NHL careers.
1976: Phil Esposito and Carol Vadnais from Boston to New York for Jean Ratelle, Brad Park, and Joe Zanussi. One star centre and defenseman for another. Worked out reasonably well for both teams, but a slight edge to Boston because Park lasted longer than the others.
1990: Chris Chelios and a 2nd rounder from Montreal to Chicago for Denis Savard. Savard won a cup with the Habs, but the price was huge.