1. Terry Ryan
Position: Left Wing
Selected: 8th overall, 1995 NHL Entry Draft
Honestly, I hate to do this. For those of you not aware, Ryan has actually written a book about his experiences in hockey, entitled Tales of a First-Round Nothing, My Life as an NHL Footnote, which I’d recommend you take a look at if you haven’t. It’s an interesting, personal dive into the life of the numerous brief blips that appear on the NHL’s seemingly never-ending radar. Similarly, Ryan’s career after leaving the Canadiens organization has been nothing short of interesting. However, ultimately, in spite of the numerous injuries and poor off-ice decisions that plagued him, Ryan’s career was just too short and unremarkable for an eighth overall pick in an extremely talented draft.
As a promising and talented winger out of the WHL’s Tri-City Americans, Ryan was a potent mix of a terrific offensive player and intimidating physical presence. Posting highs of 50-60-110 totals and 207 PM’s over 70 games in the 1994-95 season, the Newfoundland native was a playoff star and seen as a can’t miss prospect. However, off the ice, Ryan had a penchant for being hot-headed and impatient, and alienated Habs coaching and management with a know-it-all attitude, which, ultimately, along with injuries, sank his NHL chances. While Habs management took their time with Ryan giving him the occasional NHL game, he struggled in the minors with Fredericton and was in the penalty box often, posting 256 PM’s in the 1997-98 season.
After two more stints of four games in 97-98 and one game in 1998-99, Ryan refused to report to the AHL’s Quebec Citadelles (citing disagreements with head coach Michel Therrien), instead signing a minor-league deal with the St. John’s Maple Leafs in the 1999-00 season. This ultimately sank Ryan’s NHL chances, as his rights were held by the Canadiens (who refused to trade him) and he wouldn’t get playing time over other Toronto Maple Leafs prospects, as he well, wasn’t a Leafs prospect.
While he likely would’ve gotten playing time as the Habs were ravaged by injuries that season, a high ankle sprain leading up to one last chance with the Dallas Stars ultimately ended Ryan’s NHL dreams. After bouncing around several random lower-level leagues, (including an ACHL? Championship with the Orlando Seals in 2002-03) Ryan went into ball hockey, representing Canada internationally, and senior hockey, losing the 2014 Allan Cup in the finals with the Clarenville Caribous. Along with this, Ryan currently works in the film industry, with spare roles in several shows, and was slated to have a regular role in a spinoff of the hit Canadian show Letterkenny, entitled Shoresy.
Ultimately, Ryan is the, as much as I’ve said it, weirdest case on this list, as his life outside of hockey has been immensely successful and he had his moments albeit brief, in junior, the lower-level leagues, and even the AHL in bits and pieces. Unfortunately, his own shortcomings as a inexperienced, hot-headed young kid and top prospect to boot, ultimately cost him his NHL chances, in spite of being a fascinating story. Not to mention, Jean Sebastien Giguere, Petr Sykora, and Jarome “that honestly just isn’t a good look” Iginla were selected after, which is honestly just, wow. Because of this, in spite of the anomaly that is Ryan’s career both inside and outside of hockey, this ultimately lands him number one on this list.