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For years, few brands were associated with golf more than Buick—and no player was associated with golf more than Tiger Woods. The automaker reportedly paid Woods north of $50 million over eight years to brandish its logo and bring a younger edge to its products.

But in 2008—a full year before a National Enquirer exposé about his galloping infidelity would tarnish his image and make a crashed Escalade in the dark Florida night as synonymous with the name Tiger Woods as the Masters green blazer—General Motors dumped him.

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