I don't understand how that interview led to "unlikely to sign Osgood" in any fashion, except for the fact that St. James has always been part of the anti-Osgood crowd. The Wings don't have a goaltender in the system who is ready to take that step and take Osgood's job. However, Draper signing means he would be playing against Cory Emmerton, Drew Miller, Patrick Eaves, and Justin Abdelkader for a job. Which suggests that Holland's comment about 40 year-olds passing the torch was directed more at Draper than Osgood. I could be wrong. But given that Draper is a fourth line forward, and the Wings are working on re-signing forwards for the only two open spots on the roster - assuming everyone signed to a one-way deal makes the cut - that leaves Draper out. Osgood is as good as most backups and some starters, and the Wings won't be able to find an upgrade on him at anywhere near his cost. Howard is the starter, set in for long-term so they don't need to go hunting for a new guy there. A cheap vet backup or a prospect is what you'd see, and there's no options better than Osgood, unless his injury is so bad that it bothers him into next year; at which point he'll retire.
Why commit to a backup who may not even play the full year, let alone put out a consistent performance for the team?