What Did ChatGPT Call the 5 Greatest Hockey Trades in NHL History…

My thoughts:

I’m an Oilers fan, so it would be clear that I’d rank this up there, if not right at the top of the most significant trades in the history of the league. It forever changed the Oilers — a dynasty that after the move only won one additional Stanley Cup. — The trade changed hockey in the United States, especially in Los Angeles. If not for this deal, there aren’t 32 teams in the NHL. Some fans would say that’s a good thing, some might not.

ChatGPT’s No. 2: Eric Lindros to the Flyers and Rangers

They wrote:

Eric Lindros Trade (1992): The Quebec Nordiques traded Eric Lindros to the Philadelphia Flyers in a blockbuster deal that involved multiple players and draft picks. This trade had a significant impact on both franchises and shaped the future of the NHL.

My thoughts:

I remember this trade when it happened because it was such a big deal that Lindros wouldn’t put on the Nordiques’ jersey. Two teams in the Rangers and Flyers thought they had a deal in place for the rookie and both offers were massive. Eventually, it was ruled that the Flyers would get the player and what they traded to Quebec was integral in the Colorado Avalanche (who were once the Nordiques) winning the Stanley Cup.

ChatGPT’s No. 3: Jagr to the Capitals

They wrote:

Jaromir Jagr Trade (2001): The Pittsburgh Penguins traded Jaromir Jagr to the Washington Capitals in a trade that brought back prospects and draft picks. This move marked the end of an era for the Penguins and led to a new chapter in Jagr’s career.

My thoughts:

This is an interesting one to come in at No. 3 because Jagr was a Penguin through and through. He had an incredible run with that team and one could argue he was never quite the same player after he left. He did have a huge year in his first seasons with the New York Rangers from 2005 – 2007, but he moved around a lot after that.

ChatGPT’s No. 4: Messier to the New York Rangers

They wrote:

Mark Messier Trade (1991): The Edmonton Oilers traded Mark Messier to the New York Rangers in a deal that involved multiple players. This trade allowed Messier to continue his legendary career in New York and played a pivotal role in the Rangers’ Stanley Cup victory in 1994.

My thoughts:

Again, as an Oilers fan, this one stung. Messier had five really strong seasons with the Rangers after that trade, so he was certainly not a player past his prime when he was dealt. His guaranteeing a win for the Rangers in the Stanley Cup Final and then being able to make good on that guarantee was legendary.

The Oilers were going through major financial difficulties and franchise concerns and Messier was looking to cut bait while he still had a chance to win elsewhere. The Oilers got back Bernie Nicholls, Steven Rice and Louis DeBrusk.

ChatGPT’s No. 5: Orr to the Chicago Blackhawks

They wrote:

Bobby Orr Trade (1976): The Boston Bruins traded Bobby Orr to the Chicago Black Hawks (now the Blackhawks) due to financial constraints. This trade marked the end of Orr’s tenure in Boston and marked a significant shift in the NHL landscape.

My thoughts:

This is where you need to be careful with something like ChatGPT. Orr was never traded to Chicago. He signed there as a free agent after his then-agent Alan Eagleson deceived him during negotiations with the Boston Bruins who wanted to keep him and offered what was rumored to be the biggest deal in Boston sports history. Trusting Eagleson but not realizing he was being duped, Orr signed in Chicago and regretted it immediately.

Essentially, under Eagleson’s persuasion, Orr was led to believe that the Blackhawks presented him with a groundbreaking multi-million dollar contract, touted as the largest in NHL history. Relying on Eagleson’s advice, Orr made the decision to sign with the Blackhawks, assuming that the Bruins had failed to provide a comparable offer.