For the young man that toasted the shunned at the memorial I say good on him. A little self empowerment after coming out of a cult is good for you and nobody was hurt except maybe some feelings on the Jehovah's Witnesses' part. The idea that a man drinking wine and toasting the shunned at the memorial could make a Jehovah's Witness more entrenched is laughable in my opinion. On the contrary I believe they will think about it for many memorials to come and that's a good thing. It's good for them to see someone standing up against the governing body.
It reminds me a poster from years back by the name of little toe who was an elder who disassociated himself during the Sunday public talk which he was actually giving at the time. If you're interested in reading a transcript of his talk or listening to the actual talk it's here. Just look for the link on the page.