No. 1: Phil Esposito is sent to the Boston Bruins in 1967
Way back in 1967 Phil Esposito, Ken Hodge, and Fred Stanfeld were traded from the Chicago Blackhawks to the Boston Bruins in exchange for Pit Martin, Gilles Marotte, and Jack Norris.
Before being traded, Esposito was already starting to show what a potential star he could be after joining the Blackhawks at 21 years of age.
He had already put up two 50+ point seasons in his first two full years with the Hawks and the year before he was traded was just shy of a point per game after putting up 61 points in 69 games.
He wasn't the only superstar-level talent on the team either with the likes of Stan Mikita and Bobby Hull on the team among others. The Hawks had just about all the tools needed to become a dynasty before making the trade.
After being moved to Boston, Phil Esposito became a bonified superstar and one of the best goal-scorers of his era.
During his time with the Bruins, he won two Stanley Cups, five Art Ross trophies, and two Hart and Ted Lindsey trophies cementing himself in the Hockey Hall of Fame. Esposito had six seasons with 125+ points including a 76-goal season where he put up 152 points in 78 games during the 1970-71 season.
A great goal scorer, a great teammate, a great competitor – and, simply, one of the great players of all-time
— Boston Bruins (@NHLBruins) November 16, 2023
That was Phil Esposito.#NHLBruins | @rapid7 pic.twitter.com/6OVu0DQNC0
To make matters worse the two other players traded along with Esposito were no scrubs either.
Ken Hodge became a top-line forward for the Bruins where he was above or close to point per game almost every season. He even had two seasons where he reached 105 points each. Fred Stanfield was also a very consistent player for the Bruins who put up multiple 70+ points seasons during his tenure with Boston.
Both Hodge and Stanfield became two-time Stanley Cup champs after being moved from the Blackhawks.
In return, Pit Martin, Gilles Marotte, and Jack Norris were nowhere close to the value of the players the Blackhawks traded away.
Pit Martin was the best of the three players and had a pretty solid career with the Blackhawks playing at a point-per-game pace the majority of his career with his best year during the 1972-73 season where he put up 90 points. He also won the Bill Masterton Award in the 1969-70 season as well.
Gilles Marotte was a decent defenseman, and Jack Norris had basically zero impact after only playing 10 games with the Blackhawks in his career.
This trade kickstarted a golden era for the Bruins where they won two Stanley Cups during the '70s while the Blackhawks wouldn't win another cup for 43 years making this one of the worst trades in team history.