Hmmm, well the thing is I never had paticularly high hopes for Shia to be disappointed by him. Lindsay Lohan at least had some potential as entertaining eye candy if nothing else. I was never a big fan of either of them when they were "hot" so that might have a lot to do with it as well.
I agree with Lindsay winning because I at least remotely cared about her career for the most base reason.
THAT said it should be noted that Lindsay's self destruction was not just drugs and alcohol. She was also apparently a lesbian sex maniac, and a bit crazy all on her own. Her serious self destruction started when her own bodyguard quit and started outing her for her insane behavior, saying that he couldn't protect her. According to him, her MO was that she used boys for drugs, and girls for sex. She also did things like try and attack drug dealers that she thought weren't giving her a good deal, and after one such incident her Bodyguard pretty much just quit, outed his story for a quick payday, and also allegedly because he felt it was the only way to get her help, which would not be forthcoming if this was kept secret. Her other antics have apparently included things like getting wasted and trying to pick up Mariah
Carey during a red carpet event.
In a lot of respects Lindsay was kind of wild to begin with, and when she got a taste of fame and power she kind of went wild with both it, and her personal vices.
A lot of people will laugh at this, but I honestly do think Charlie Sheen is a perfect mentor for her. He's dealt with all of the same things she has been going through, including a sex addiction. Charlie, whether you think he's a mess or not has still managed to build up a massive career, even with those problems. His most recent and famous "explosion" over "Two and a Half Men" wasn't all that out of line actually, he had some very legitimate points, he just went about it the wrong way. That's a show which incidently did make over a billion dollars, and even with that explosion Charlie is still talented enough and has enough of a fan base where he was able to pre-sell his "Anger Management" show to a massive degree, to the point where even if it fails in an absolute sense (which it doesn't seem to be doing) he's still set.
The big question with Lindsay at this point is how talented she actually is, and if she's capable of recovery. To put it bluntly in a lot of the recent pictures of her, she is physically ravaged to a point I don't think i've ever seen Charlie Sheen hitting at his worst (of course maybe the camera didn't catch him at that point). The sex, drugs, stress, and everything else have seriously damaged her looks, and I'm not sure if she'll ever get them back. She could succeed on talent without them, but again it's hard to say if she's that good due to her relatively limited body of work.
I'll also be blunt, typically with actresses the illusion of availibility to men is a big part of their selling point. In Lindsay's case, I think she kind of blew presenting that illusion, since a lot of the self destruction rumors I heard about it made it pretty clear that she's a lesbian, even if she's bi-, she definatly seems to be swinging towards the girl's camp. I think the best thing for her, and probably her career honestly, would be for her to find someone at this point, either a steady girlfriend, or a wife. Mostly because of the stability such a relationship would likely provide. The "damage" already being done she'd benefit most from a long-term anchor. I can see Charlie mentoring her to some extent, but I don't think he'd be capable of being that simply because he has his own career to worry about.
Such are my thoughts.