Our favorite New York "writer" Derek Blasberg (pictured at right, at Homecoming 1999) was always destined for greatness. Even at an early age, living in a well-to-do suburb of St. Louis, where others may have accepted their suburban lot, he saw that there was another world out there—a world where he could safely escort Genevieve Jones, break up Proenza Schouler, and possibly edit Socialite Rank. In high school, he was already a hit with the ladies—on the back of this photo, he scrawled, "Wish this was you, toots! Love, Derek," and our mole tells us he reportedly sent this exact same message and photo to several other lasses. This enterprising classmate also sent along some other revealing items to Gawker HQ, which you can peruse after the jump.
Above, Blasberg's politically active past.
At right, from his yearbook: Most Likely to Succeed. How right they were.
And below right, his yearbook photo.