Over the weekend we first learned that Conklin and the Red Wings had talked about a possible reunion. A day later, Ken Holland said that he will probably make a decision sometime this week about the Red Wings' backup goalie situation. While he also said the Red Wings would be comfortable with Chris Osgood coming back for a season, Holland made that sound like nothing more than a last resort move for the team.
If Conklin does in fact sign with the Red Wings, he will serve as Jimmy Howard's backup. In the 2008-09 season, Conklin was brought to Detroit to be Osgood's backup, but he got quite a bit of playing time. In fact, Conklin won only one less game than Osgood during the regular season.
Should the Red Wings decide to sign Conklin, chances are Osgood will announce his retirement. It's not expected Osgood will try to play with another team if Detroit doesn't offer him a deal, so his time in the NHL could be coming to an end.