Really? I did not know this.
Just for the excuse to go down memory lane....
In the 1995 CBA, the NHL added compensatory picks for 1st rounders who didn't sign. In those days the rookie salary cap was just added but it wasn't like how it is today. The spirit of the rule was to help teams get something back if they got spurned by the player. Although in some cases, the team realized they drafted a dud and that they'd rather have the mulligan.
1998: Devils got the 37th pick (10th pick of the 2nd round) for not signing Lance Ward (10th overall in 1996). Definitely a case where the team wanted a redo (insert joke about Lou bending the rules here). Ward would get redrafted 63rd overall by Florida.
Colorado got #53 for not being able to sign Peter Ratchuk. It appears Ratchuk was the first to use the NCAA to CHL loophole to become an unrestricted free agent since he was too old to re-enter the draft. Ratchuk would sign with Florida.
1999: Washington got #37 for not signing Nick Boynton. As I remember it, Washington nearly traded Boynton to Chicago for #23 before his rights expired but something happened. Boynton would be redrafted #21 by Boston.
LA opted not to sign Matt Zultek and got back pick #43. Zultek would be redrafted #56 by Boston.
Colorado got pick #54 for not signing Kevin Grimes who would go undrafted in 1999.
2000: Islanders got pick #39 for not signing Mike Rupp. Rupp would be redrafted #76 by New Jersey.
Maybe one of the more infamous instances was Mathieu Chouinard and Ottawa. There was a lot of front office turnover after Chouinard was drafted in the 1st round in 1998 and he got a last minute contract offer in 2000. He didn't like how Ottawa refused to negotiate so he declined to sign. Ottawa got pick #45 as compensation and proceeded to use that pick to take Chouinard again. Chouinard said he punched a wall when he found out.
New Jersey got pick #56 after Mike Van Ryn used a loophole to become a free agent. The two sides went to an arbitrator a few weeks earlier to determine his status. Van Ryn would sign with St. Louis a few weeks later.
One personal favorite outlier was the league giving Boston pick #66 (1st pick of the 3rd round) as compensation for Ben Clymer (1st pick of the 2nd round in 1997) using a loophole to become a free agent. Boston must have argued that while Clymer was technically a 2nd rounder (#27) in 1997 that there were now 30 teams in the league after expansion and the NHL threw them a bone.
2001: Phoenix got #45 for Scott Kelman not signing; Kelman went undrafted the second time.
Buffalo got #50 for Barett Heisten who used the Clymer/Van Ryn loophole to sign with the Rangers.
2003: Chicago got #59 for signing Adam Munro who went undrafted the second time. Oddly Munro would eventually sign with Chicago.
2004: Rangers got #46 for R.J. Umberger not signing. Umberger went the August 15th route to sign with Philadelphia.
Dallas got #56 for not signing Martin Vagner; Vagner would be redrafted #268 by Carolina.
2005: LA got #60 for David Steckel. As I remember it, LA preferred the pick after Steckel didn't impress on a minor league deal with LA's farm teams. Steckel would sign with Washington.
2006: Boston got #37 for Lars Jonsson. Edmonton got #45 for Jesse Niinimaki. LA got #48 for Jens Karlsson; LA's scouts wanted to draft Milan Lucic with #48 but new GM Dean Lombardi forced them to take a defenseman.
2007: Minnesota got #42 for A.J. Thelen.
2008: Phoenix got #35 for Blake Wheeler refusing to sign.
2009: Rangers got #47 for Alexei Cherepanov (RIP)
2011: Montreal got #50 for declining to sign David Fischer.
2012: San Jose got #55 for declining to sign Patrick White who was acquired from Vancouver; San Jose likely knew they weren't going to sign him and that they'd have the pick in their back pocket.
2013: Winnipeg got #59 for not signing Daultan Leveille who was drafted in 2008 by Atlanta.
2015: Chicago received #54 for Kevin Hayes declining to sign.
2016: Coyotes got #53 after they didn't sign Conner Bleackley; They got Bleackley at the trade deadline but they weren't going to sign him.
2022: Minnesota got #56 for not signing Filip Johansson.
2024: Philadelphia got #51 for not signing Jay O'Brien.