I've always been a huge Osgood fan, but I also think unless the HHOF really lowers the standards for goalies they let in, he belongs firmly entrenched in the Hall of Very Good, as well as the Hall of Feel Good with his redemption winning the 2008 Cup.
I think the bolded is something that frequently gets glossed over in Osgood HHOF debates. Probably especially from people who didn't see all or at least most of Osgood's NHL career and are just going by the numbers.
Unlike his same era HHOF and HOVG contemporaries, Osgood didn't have a typical "peak" or "prime" career arc where he was some in demand highly regarded starting goalie. At 28YO, he was in a lame duck spot with the Wings looking to move him, but ultimately couldn't put together a trade and he moved in the waiver draft. At 32YO, he comes out of the lockout spending some time getting ripe in the UFA bargain before he comes back to Detroit for peanuts - A move that doesn't really get a whole lot of enthusiasm out of the fan base. Most of those contemporaries would not have found themselves in those spots at those ages.
And as for career arc, his isn't really an "arc" but more of a rollercoaster ride:
-Hard to blame him given he was a 21YO rookie, but his surprise 1st year ends with an infamous gaffe that leads to the Wings losing in the 1st round to a barely out of the expansion draft Sharks
-Osgood was ultimately never able to overtake Mike Vernon in the 3 years they platooned. At least when it came to their play on the ice.
-You'll never have a hard time finding someone that will say the '98 Cup was won "in spite of Osgood" and they might easily recall the Jamie Langenbrunner red line WCF OT squeaker and other questionable goals against from those playoffs
-Was a big part of the Islanders surprise resurgence in 01-02, but then gets cast off the next year when he gets injured and then outplayed by Garth Snow
-His forgettable tenure with the Blues is marked by a 1st round collapse after being up 3-1, and then a pretty easy 1st round elimination the next year
-He returns to Detroit expected to be the starter, but groin injuries ruin his opportunities the first year, then he takes a back seat to Hasek for a 2nd time, where injuries help keep him in the #2 spot
-Between his Cup win as a starter in '08 and a stellar run to game 7 of the '09 SCF is an absolutely abysmal regular season
-He barely starts after Jimmy Howard takes over the starting job, and then he retires with little fanfare after an injury ends his last season.
Up until he finally won the Vezina, I thought that MAF might end up being a close comparable to Osgood. Similar career arcs with multiple Cups/finals appearances with a mixed bag as to whether they were starter or backup, fanbase scapegoating, "in spite of" or "played behind good teams" narrative behind successes, unexpected success with a new team after going there in a "draft" of NHL talent and then a late career redemption.
The only example that might muddy the water in terms of being "highly regarded" would be Bill Ranford. For years during the 90's, the media continually pushed him as a top goalie in the league while he put up pedestrian numbers for the Oilers and had to play like garbage for the Bruins and Caps before they finally relented.
