Beyond the Red Border: How D.W. Pine Shaped Time’s Boldest Covers

D.W. Pine, Time magazine’s longtime creative director, recently celebrated the publication of his thousandth cover — a milestone reflecting his deep impact on modern media. Since joining Time in 1998, Pine has placed some of the world's most recognizable figures within the iconic red border, from global leaders like Pope Francis and Vladimir Putin to business moguls and celebrities.

Not every cover under Pine’s leadership was designed to provoke, yet many have sparked powerful debates. He oversaw provocative editions such as the 2012 “Are You Mom Enough?” cover, featuring a mother breastfeeding her 3-year-old son, and the striking 2010 “Aisha” cover, which showed an Afghan woman disfigured by Taliban brutality. These images, according to Pine, succeeded because sometimes a simple, raw visual can cut through a saturated media landscape louder than a thousand words.

While controversy often swirls around Time’s covers, Pine emphasized that not every cover aims for shock value. Often, the magazine highlights figures — from CEOs to cultural icons — who may not seem provocative but hold immense importance. Knowing when to push boundaries and when to simply inform is key, Pine explained, calling the covers “journalist posters” that balance sensitivity with boldness.

Pine particularly values the power of imagery over text, opting to let the pictures speak on their own. He cited the February cover featuring Elon Musk behind the Resolute Desk as an example, using minimal symbolism: Musk, casually holding a coffee cup, suggested normalcy amidst great influence. It didn’t need words to signal that Musk was pulling major levers behind the scenes.

Former President Donald Trump has had a complicated relationship with Time’s covers, appearing 45 times — second only to Richard Nixon’s 55 appearances. Pine recalled that during Trump’s first term, nearly every week felt cover-worthy due to the administration’s unpredictable nature. However, with Trump’s second term underway, Pine noted that the shock factor has lessened, and Time's approach will adapt accordingly.

Already, Pine’s editorial decisions have drawn Trump’s attention. After Musk was depicted behind Trump’s iconic desk, the president questioned Time’s relevance, jokingly asking, “Is Time magazine still in business?” Pine brushed off the comment, pointing out Trump’s long-standing fascination with Time covers — he’s honored when featured, yet admits he likes only about 20% of them.

Looking ahead, Pine expects that Trump will eventually surpass Nixon as Time’s most-featured individual, a symbolic milestone that will undoubtedly stir more controversy. For Pine, though, provoking conversation is exactly the point: "If no one was talking about us," he said, "then I think we’d have a problem."