Sentiment Analysis of microblog feeds has attracted considerable interest in recent times. Most of the current work focuses on tweet sentiment classification. But not much work has been done to explore how reliable the opinions of the mass (crowd wisdom) in social network microblogs such as twitter are in predicting outcomes of certain events such as election debates. In this work, we investigate whether crowd wisdom is useful in predicting such outcomes and whether their opinions are influenced by the experts in the field. We work in the domain of multi-label classification to perform sentiment classification of tweets and obtain the opinion of the crowd. This learnt sentiment is then used to predict outcomes of events such as: US Presidential Debate winners, Grammy Award winners, Super Bowl Winners. We find that in most of the cases, the wisdom of the crowd does indeed match with that of the experts, and in cases where they don't (particularly in the case of debates), we see that the crowd's opinion is actually influenced by that of the experts.