The New York Rangers, like any NHL franchise with a long history, have had their share of regrettable trades. These deals, often made with the hope of improving the team's chances, can backfire spectacularly, setting the team back years. Here are five of the worst trades in Rangers history, deals that haunt fans to this day.

1. Rick Middleton for Ken Hodge (May 26, 1976)

This trade is almost universally considered the worst in Rangers history. In an effort to reunite Phil Esposito with his former Boston Bruins linemate, Ken Hodge, the Rangers traded away a promising young winger in Rick Middleton. Hodge, while a decent player, was past his prime, whereas Middleton went on to become a star for the Bruins. Middleton played 12 seasons in Boston, scoring 402 goals and amassing 898 points. Hodge, on the other hand, played just one full season for the Rangers, scoring 21 goals. The deal is a classic example of trading potential for past performance and it backfired tremendously.

2. Sergei Zubov and Petr Nedved for Luc Robitaille and Ulf Samuelsson (August 31, 1995)

In 1994, Sergei Zubov led the Rangers in scoring during their Stanley Cup championship season. Just a year later, he was shipped to Pittsburgh along with Petr Nedved for Luc Robitaille and Ulf Samuelsson. The Rangers felt Zubov was physically overwhelmed in the playoffs. While Robitaille was a proven scorer, he didn't fit in New York and was traded after two seasons. Zubov, however, went on to have a Hall of Fame career, excelling with the Dallas Stars. Samuelsson provided some grit, but the loss of Zubov's offensive talent from the blue line was a major blow.

3. Ryan McDonagh and J.T. Miller to Tampa Bay Lightning (February 26, 2018)

This trade signaled the Rangers' official rebuild. While rebuilding isn't inherently bad, the return for McDonagh, a top-pairing defenseman, and Miller, a skilled forward, hasn't lived up to expectations. The Rangers received Libor Hajek, Brett Howden, Vladislav Namestnikov, a first-round pick in 2018, and a second-round pick in 2019. While the Rangers acquired Nils Lundkvist with the first-round pick, he was later traded. None of the players acquired have become impact players for the Rangers, while McDonagh continued to be a valuable defenseman for the Lightning, winning two Stanley Cups.

4. Mike Ridley, Kelly Miller, and Bob Crawford for Bob Carpenter and a 2nd Round Pick (January 1, 1987)

This trade from the mid-80s is another example of the Rangers giving up valuable assets for underwhelming returns. Mike Ridley and Kelly Miller were solid contributors, while Bob Carpenter never lived up to his potential in New York.

5. Marc Savard to Calgary Flames (June 26, 1999)

In this deal, the Rangers traded a promising young center in Marc Savard to the Calgary Flames for Jan Hlavac, a swap of 1999 first-round picks, and a 1999 third-round pick. Savard went on to have a successful NHL career, while Hlavac had a decent but unspectacular run with the Rangers. The Rangers used the acquired draft picks, but failed to find players of Savard's caliber. This trade is a reminder that sometimes the best move is to be patient and let young talent develop.