This is what Maltby did a number of years ago. Get a contract. If it works out and he outplays the kids, then that's fine. He deserves to be on the team. If not, he retires and that's that. Everyone was mad at Malts for hanging around until he retired. Then everyone got some clarity and said, "Hey. He was just giving it another shot." and all was well.
I don't blame Cleary or Holland. In Holland's case, it was a win-win. If Cleary REALLY outplayed the kids (as if) he's be icing the best team possible. If Cleary didn't, then he'd either have a great guy in GR or he could let him go in peace. In either case, giving the kids a little more competition never hurts, and they got the benefit of Cleary's teaching while he was there. Remember that game when he and Larkin were on the bench after their shift? Larkin was intent on what Cleary was explaining to him. Since Cleary didn't play during the season, it didn't cost the Wings a dime.
In Cleary's case, it was a chance. It was one more training camp. One more pre-season. One more time hearing the roar of the crowds and feeling the comradery in the locker room. One last hurrah before skating off into the sunset.
I wish him well. I will always remember him as the Guy Who Almost Lost an Eye Fighting Chris Elbowf*** Pronger.