The Art of Provocation: D.W. Pine and the Power Behind Time Magazine’s Bold Covers

D.W. Pine, Time magazine’s longtime creative director, has spent decades shaping some of the most iconic and controversial covers in journalism. Since joining the magazine in 1998, Pine has placed world leaders, innovators, and cultural icons — from Pope Francis to Kim Jong-un — within Time’s famous red border, recently celebrating the milestone of publishing his thousandth cover.

Not all of Pine’s covers aim to spark debate, though many have. He refers to the covers as "journalist posters," noting that their power often lies in featuring not just political figures but CEOs and celebrities who, while not inherently controversial, are significant in shaping our world. According to Pine, the real skill is knowing when a provocative image is necessary to make a point — and when a quieter, simpler message can speak louder.

Among the most talked-about covers under Pine's direction were the 2012 "Are You Mom Enough?" featuring a young boy breastfeeding, the 2010 “Aisha” cover spotlighting an Afghan woman mutilated by the Taliban, and the 2017 "Nothing to See Here," portraying President Donald Trump amidst a storm in the Oval Office. Pine explained how these divisive images could convey multiple, sometimes conflicting, interpretations depending on the viewer’s perspective.

For Pine, minimalism on the cover is key — letting the imagery speak volumes without excessive text. He pointed to Time’s February cover featuring Elon Musk behind the Resolute Desk. Pine emphasized the symbolism: Musk, pulling strings of influence while casually sipping coffee, portrayed a surreal blend of power and normalcy. It was a visual metaphor that didn’t need words to be understood.

Trump, who has been named Time’s Person of the Year twice and appeared on the magazine’s cover 45 times, has a complicated relationship with Time. Pine recalled that during Trump’s first administration, nearly every week felt momentous enough to warrant a cover story. However, Pine now believes the shock factor has diminished, and future covers will reflect a different tone as Trump's second term unfolds.

Pine’s editorial choices have often caught Trump's attention. After the Musk cover, Trump sarcastically questioned Time’s relevance, asking if it was "still in business." Pine took it lightly, recognizing Trump’s long-standing fascination with Time covers — even admitting that the former president has said he only likes about 20% of them. Regardless, Trump’s continued presence ensures he will likely surpass Richard Nixon's record for most Time covers by the end of his second term.

Despite any backlash, Pine sees controversy as a vital sign of relevance. Whether celebrating, questioning, or criticizing power, Pine believes that if people are talking about Time’s covers — even angrily — it means they are paying attention. “We want to be able to question authority,” Pine said. “If no one was talking about us, then I think we’d have a problem.”