With the Kevin Shattenkirk tenure coming to an unceremonious end as the Rangers bought out the final two years of his contract earlier this week, memories of the club’s past woebegone decisions were awakened.

Shattenkirk came to the Blueshirts in 2017 as a free agent with a bit of a hometown discount, and with all the right intentions to help elevate the team he grew up rooting for as a kid in New Rochelle. But a knee injury in his first training camp and subsequent other injuries limited his effectiveness, and helped bring about the organization’s earnest campaign of rebuilding — one that has proven to be quite fruitful and advanced in its timing.

But where does the Shattenkirk signing rank among the biggest free-agent disappointments in Rangers history? Just for some perspective, he’s not even close to the top-5 busts. Here’s a look:

5. Brian Skrudland/Mike Keane. General manager Neil Smith was trying to add some veteran leadership around Wayne Gretzky in the summer of 1997, so he signed Panthers captain Skrudland to a three-year, $5 million deal, and also added Keane, a former Cup-winner with the Avalanche and previous Canadiens captain, to a four-year, $8 million deal. By the middle of their respective disappointing seasons, and with the team on the verge of missing the playoffs, the two players were sent to the Stars in exchange for Todd Harvey. The most notable moment of their tenure was Keane accidentally slamming into teammate Pat LaFontaine during a March game against the Senators. It was the final NHL game for the terrific LaFontaine, as he suffered another of his countless concussions that resulted in his retirement in 1999.

4. Scott Gomez. He had been such a good player with the Devils for eight years, the Rangers thought they were getting the playmaker they coveted when they signed the outgoing Alaskan in 2007 to a seven-year, $51.5 million deal. Gomez actually had a pretty good first year, putting up 16 goals and 54 assists, but it fell to 42 assists in his second year and the return on investment was extremely low. Yet the deal was salvaged by one of (if not the) best trade GM Glen Sather made, sending Gomez’s bloated deal to the Canadiens in exchange for Chris Higgins and soon-to-be Rangers captain Ryan McDonagh.

3. Bobby Holik. In another attempt to pull from the well of Lou Lamoriello’s championship Devils, Sather signed the defensive-minded center in 2002 to a huge five-year, $45 million deal. Holik was never going to impress with his offensive numbers, and the pressure of the big contract affected his entire game. He lasted just two seasons with the Rangers before being bought out, playing the next three years with the Thrashers — who were swept in the first round by the Rangers in 2007 — before a farewell season in New Jersey in 2008-09.

2. Theo Fleury. This was a marriage that was destined to fail, as the small-town Fleury had dealt with substance-abuse issues in the past that the bright lights of Broadway were not going to help. But Smith overlooked the personal issues and focused on the diminutive winger’s 40-goal season the previous season split between the Flames and Avalanche. The four-year, $28 million deal in 1999 blew up in the Rangers’ faces, as Fleury continued to have issues on and off the ice that overshadowed his occasional brilliance between the whistles. The club didn’t pick up the fourth-year option, and Fleury finished his career with one more season for the Blackhawks in 2002-03.

1. Wade Redden. Maybe the expectations were far too high when Sather signed the Ottawa defenseman to a bloated six-year, $39 million deal in the summer of 2008. The hope was Redden could be an offensive threat from the back end, the power-play quarterback the Rangers needed. He was woefully incapable of that, putting up just five goals in 156 games over his two full seasons with the Rangers. He was placed on waivers during training camp in 2010 and spent the next two seasons as the highest-paid player (by far) in the AHL. The team used a compliance buyout to rid themselves of the remaining two years, and the league adopted the “Redden Rule,” severely limiting the amount of salary-cap savings a team can have while burying a player in the minors.