Source : Webster's Revised Unabridged Dictionary (1913)

   8. Brisk; fresh; as, a smart breeze.

   {Smart money}.
      (a) Money paid by a person to buy himself off from some
          unpleasant engagement or some painful situation.
      (b) (Mil.) Money allowed to soldiers or sailors, in the
          English service, for wounds and injures received;
          also, a sum paid by a recruit, previous to being sworn
          in, to procure his release from service.
      (c) (Law) Vindictive or exemplary damages; damages beyond
          a full compensation for the actual injury done.
          --Burrill. --Greenleaf.

Source : WordNet®

smart money
     n 1: money bet or invested by experienced gamblers or investors
          (especially if they have inside information)
     2: (law) compensation in excess of actual damages (a form of
        punishment awarded in cases of malicious or willful
        misconduct) [syn: {punitive damages}, {exemplary damages}]
     3: people who are highly experienced or who have inside
        information; "the smart money said Truman would lose the
        election"