Reviewing Jeff Gorton's Trade History

Best
Tuukka Rask for Andrew Raycroft
Gorton made this deal while as the Interim General Manager of the Boston Bruins. At the time the Bruins had 3 starting goaltenders and the Maple Leafs were desperate to find a goaltender.

Rask went on to win 306 games for the Bruins, was part of their Stanley Cup team and won the Vezina in 2014.

It turned out that Gorton's first move might have easily been his best.

Worst
Drafting Lias Anderson
The 2017 NHL Draft was ultimately not a good one, but Lias Anderson at 7th overall ultimately ended up making the Derek Stepan trade return much less appealing.

Adam Fox
Adam Fox for 2019 2nd Round Pick & 2020 2nd Round Pick
It seems like Gorton has a gift for trading for players that eventually win some NHL hardware. On April 30th, 2019 Gorton acquired Adam Fox in exchange for two 2nd round picks.

Fox immediately went on to play a huge role in the New York defence and captured the Norris Trophy in 2020-2021.

Worst
Not selling high on Alexander Georgiev
The Rangers had a chance to create a bidding war on their star backup goalie, but Gorton and his management team set the price too high and overplayed their hand. Not only did they not manage to get anything for Georgiev but the goaltenders play has fallen off substantially since he peaked.

Best
Mika Zibanejad and a 2nd round pick for Derick Brassard and a 7th round pick
Somehow Jeff Gorton managed to convince the Senators to send them the better player on the deal, while also convincing them to send him the better of the two picks involved.

Zibanejad has gone on to score 20 goals four times for the Rangers and 40 goals once, while Brassard didn't even accomplish 40 goals over his two seasons in Ottawa.

Worst
Ryan McDonagh and JT Miller for Namestnikov, Howden, Hajek, a 1st, and a 2nd
At the time the return didn't make sense and the fact that the Rangers had to throw in JT Miller to get the deal done made it even worse. All the Rangers have left to show for this deal at this point is Nils Lundkvist and an unimpressive Libor Hajek.

The Lightning eventually flipped Miller for a 1st round pick making this deal look even worse.

Best
Derek Stepan and Antti Raanta for Anthony DeAngelo and 1st round pick
Ultimately this trade didn't work out as well as the Rangers would hope as neither the pick or DeAngelo would ultimately moving out the final 4 years of Stepan's contract was one of Gorton's best moves.

Worst
Signing Kevin Shattenkirk & Buying him out
The Rangers signed Kevin Shattenkirk to a four year, $6.6 million deal. He even took a hometown discount to play for his favorite team.

He was then rewarded by playing with Ryan McDonagh for a whole 4 shifts and then being sent to the 3rd pair and 2nd powerplay.

Shattenkirk was bought out after 2 seasons and the Rangers took on a $6,000,000 dead cap space because of it.