On Broadway, top bookmaker Oscar 'Odds' Owen, [Warren William], loses a hefty $50,000 when a racehorse owned by Everett Markham turns out to be doped. After uncovering the ruse, Owen confronts Everett and makes it clear that the implicated horses will be sold and the debt paid back. The sting of that setback nudges Owen to dream bigger, and the spark comes from a stock idea he admires after hearing about Lloyd's of London: a world where unusual perils are insured with calculated wit and risk.
Owen’s misadventure with Markham plants the seed for a new business plan: he will underwrite unusual insurance policies that others wouldn’t dare touch. This is where the film pivots from racing to a brisk, cagey game of propositions, counterclaims, and sly incentives, all powered by Owen’s keen eye for human folly and fortune. The idea isn’t just about money; it’s about manipulating probabilities in people’s lives the way a bookie handles odds.
Marilyn Youngblood, [Claire Dodd], is the charming focal point around which much of the comedy centers. She supports her father, Col. Youngblood, [Guy Kibbee], and she carries a complicated love life—dating the wealthy, hypochondriac Dwight Boardman, [Walter Byron]. Everett Markham, a friend to Marilyn, convinces her father to take out a three-year insurance policy on Marilyn herself, promising a payout of 50,000 if she marries within that window. Owen, ever the opportunist, agrees to insure this curious arrangement, setting the stage for a collision between affection and avarice.
To weaken Dwight’s hold and push the plan forward, Owen’s men craft a sly ruse: they persuade Dwight that marriage could be dangerous for a man with a weak heart. It’s a calculated, almost carnival-like manipulation designed to push Marilyn toward other options while keeping Owen’s own hands clean of any direct interference.
Marilyn soon encounters a new partner, David Van Dusen, played by [Errol Flynn], and the romance quickly engages the audience’s sympathy and suspicion in equal measure. Owen’s crew shadows the couple and crashes a restaurant scene where Marilyn and Van Dusen dine. They pose as shady figures who “know” Van Dusen, and the plot thickens: one man hands Van Dusen an envelope containing money, while another slides a gun wrapped in a handkerchief into the scene. Unable to shake the odd impression, Marilyn interprets Van Dusen’s behavior as gangster-like, and she ends the relationship on the spot.
Owen, though, is not a passive observer. He notices Marilyn’s disapproval and, despite himself, becomes drawn to her. He starts dating Marilyn, ostensibly to keep her from other suitors, even as his heart grows more entangled with her in ways that money and policy constraints cannot easily explain.
The insurance scheme moves toward its next dramatic turn when Marilyn’s father explains the policy in detail. Marilyn resolves to dramatize Owen’s feelings by making him fall for her, and, to her surprise, Owen does fall—in love, that is, even as he remains professionally tethered to the policy’s cold logic. Marilyn, seeking her own revenge, agrees to marry Everett Markham in order to deprive Owen of both his wealth and the woman he seems to be learning to love. Everett, in turn, believes he can win Marilyn back and outmaneuver Owen, but Owen’s feelings complicate his own calculations.
As the wedding day approaches, the tension between heart and wallet intensifies. Marilyn’s father pleads with Owen to pull back, to save the arrangement from collapsing under its own contradictions. Marilyn, too, quietly hopes the wedding won’t happen. When Everett never appears at the church, the moment of truth arrives: Owen steps in as the groom, and Marilyn walks down the aisle to meet him with a sense of relief and triumph. In a final, comic flourish, Owen’s men grease the wheels of civic life by paying off cab drivers to create a traffic jam, ensuring Everett cannot reach the church in time.
What follows is a rippling, lighthearted exploration of how risk, romance, and reputation intersect in a world where every bet and every vow can be insured or undermined. The film balances fast dialogue, caper-like set pieces, and a surprisingly tender core as two people discover that what starts as a purely financial calculation can, in the right moments, grow into genuine affection.
