Abstract: We explore a model of litigation where the plaintiff can acquire a financial position in the defendant firm. The plaintiff gains a strategic advantage by taking a short financial position in the defendant’s stock. First, the plaintiff can turn what would otherwise be a negative expected value claim (even a frivolous one) into a positive expected value claim. Second, the short financial position raises the minimum amount the plaintiff is willing to accept in settlement, thereby increasing the settlement amount. Conversely, taking a long position in the defendant’s stock puts the plaintiff at a strategic disadvantage. When the capital market is initially unaware of the lawsuit, the plaintiff can profit both directly and indirectly from its financial position. When the defendant is privately informed of the merit of the case, the plaintiff balances the strategic benefits of short position against the costs of bargaining failure and trial. When credibility is an issue, short selling by the plaintiff can actually benefit both the plaintiff and the defendant by lowering the settlement amount and also reducing the probability of proceeding to costly trial.