It doesn't matter if you finish third or last, either way if it is not first or second, then you've lost.
Every draft I pick the guys that other owners leave because of the risk. Two years ago, it paid off when I drafted Vlady in the second round and the Big Unit in the third (both were coming back from injury that year), and last year it burned me when I drafted Bonds in the second round and Nomar in the third. In the first case, I won the pool, in the second case, I came in last. I have no regrets.
Having said that, as I do agree with the above post, only take as much risk as is necessary, but in a competitive league, you are not going to win by playing it safe.
An unanswered question is better than an unquestioned answer