Much has changed since 2001, when creative director D.W. Pine produced his first cover for TIME. (That cover, for a story about online privacy, rendered a desktop computer as a heavy-duty lock.

If a picture is worth a thousand words, then D.W. Pine, Time’s creative director of 26 years who recently published his thousandth cover, certainly has a lot to say.

In a provocative move that could be aimed at stoking President Donald Trump’s ire, Time magazine’s latest print cover features Elon Musk behind the Resolute Desk in the Oval Office. The ...