A common rumor in the 1990s was that Timberland's former chief executive, Jeffrey Swartz—the grandson of company founder Nathan Swartz—didn't like black people buying his products, and had some kind of racial animus towards Timberland's African American clientele.

The source of this rumor is likely Swartz's own words, largely taken out of context. In a 1993 New York Times article detailing the boots' increasing appeal among hip-hop fans, Swartz described his intended audience thusly: "honest working people." This is innocent language on its own, but obviously loaded in a racial context.

But it wasn't the hip-hop world that perturbed him about Timberlands' new fanbase at the time; it was fashion trends in general. Times reporter Michael Marriott described the company's mantra thusly: "Timberland must forever favor what is functional over what is fashionable." What concerned Swartz wasn't the race of his consumers; it was the fickle nature of relying on fads to dictate the direction of business.

In fact, Swartz was, until he sold the company a couple years ago, one of the more progressive executives in the United States. In the early 1990s, he funded an anti-racism advertising campaign, and has long had an environmentally-friendly record. But he did indicate some greater understanding of where things went wrong when he was interviewed by the Financial Times after he sold Timberland to VF Corp in 2011:

"The data was excruciatingly clear if we had had the brains to understand it. A young kid wearing outdoor hiking boots in city fashion ... It wasn't a caricature," he said. Instead, it connected back to the essence of the brand.

He added that, even in concrete jungles, "people said 'with Timberland boots on our feet we feel nothing can stop us ... I live in a rugged world and I want to feel powerful and secure'."