Mathieu Chouinard was drafted by Ottawa in the first round and didn't sign. When he re-entered the draft Ottawa picked him again in the second round
Just to expand on Chouinard, it wasn't totally his fault.
A few days after he was drafted, Pierre Gauthier resigned as GM and was replaced by Rick Dudley. A year later, Dudley left and took the GM gig in Tampa. Dudley was eventually replaced by Marshall Johnston.
Chouinard said that he had minimal contact with Ottawa through their front office turmoil. As his rights were set to expire, he was presented with a low ball take it or leave it offer. Chouinard was offended and decided to go back into the draft. Ottawa's new GM may have played hard ball knowing they would receive a compensatory 2nd.
Comically Ottawa would take Chouinard with that compensatory pick. Chouinard said he punched a wall when he found out.
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There was a little bit more motivation in those days for a player to re-enter the pool if he thought he could go higher. There was a rookie salary cap but it wasn't as stringent as ELCs are today. For instance Mike Comrie got a 3 million dollar signing bonus as Edmonton was worried he was going to use the free agent loophole.
Scott Parker was a Devils third rounder in 1996 but he had a big D+2 season and some projected him to go in first round in 1998. Lou declined Parker's salary demands and he went back into the pool. Boston had something similar with a guy named Kyle Wanvig; Boston had a trade in place that got nixed due to a jammed fax machine.
1995-2004, a team owned a player (for the most part) until he was 31. So there was more reason to be picky.
Whereas nowadays a blue chipper could be a UFA at 25, so it makes more sense to get your free agent clock rolling.