John Vaile thought his buddy had found a sure thing with “Drunk Boat,” a coming-of-age film starring John Malkovich and John Goodman.
Though his friend, former Chicago Board Options Exchange trader Tommy Tomaska, had produced some forgettable movies before, Mr. Vaile had high hopes for the new film because of its star cast and financial support from an unnamed deep-pocketed Chicago investor who’s a fan of Mr. Malkovich…