"He Had a Painter's Cap / It Had Flaps On the Back"

The Crimson has a long-standing tradition whereby everyone who serves as president gets his or her portrait drawn by this old caricature artist named David Royce. Royce was a member of the staff in the 1950s and from what I hear he is a pretty cranky dude. He makes everyone wear a hat in their portrait, and he apparently corresponds with whoever he's drawing for weeks in advance trying to decide what kind of hat best represents their personality. (WCM '07, a dedicated patriot, chose a three-corner cap in the style of Paul Revere, etc., and Royce almost didn't let him do it because he didn't think it was a vivid enough encapsulation of his personality.)

All of which makes me wonder: who will be the first Crimson president to wear a trucker hat in their portrait? I hope alumni are informed.