In the early-2000s, there was CrossGen Comics. It sought to be an alternative to Marvel and DC Comics, signing up top talent to exclusive contracts and relocating them to their headquarters in Florida. I didn't get into their books beyond borrowing trade paperbacks from the library, but I found myself gravitating towards their booth at major conventions. You could always get a free sketch from the artists there, as long as it was a CrossGen character. I don't remember meeting Dale at Comic-Con International in 2003, but I got a nice-looking drawing of Samandahl Rey, the hero of the sci-fi series Sigil.
The next time I heard of Dale, it was in the run-up to DC Comics' "event" of 2005, Infinite Crisis. The company had four miniseries leading up to it, and one of them was written by Gail Simone, whom I befriended on the Kingdom Come forum in 1996. On the surface, Villains United was supposed to be about the gathering of supervillains as a group. However, the real focus was on six "bad guys" who would turn against the cadre. The miniseries was penciled by Dale, and it kicked a lot of ass. From 2005-2007, I would get sketches of three of the antiheroes that would later form the nucleus of Secret Six: Ragdoll, Scandal Savage and Catman.
The last time I would see Dale was at Canadian Fan Expo (now Fan Expo Canada) in 2007. He was the penciller on Justice Society of America by this time, and the series was going to feature Superman straight from Kingdom Come. I had been getting sketches of characters from that miniseries, and I wound up getting Dale to draw an exo-suit-wearing Bruce Wayne for me.
That would be the last time I remember seeing Dale. He's still around . . . he's been the cover artist of the latest iteration of Secret Six. I was trying to avoid him on the last day of CFE, because I had lost my camcorder and my sketchbook, and I didn't want him to see me in a fragile state of mind. I was in a really bad place at the time. While I wouldn't get the camcorder back, somebody did find the sketchbook. That was more important to me.
HONORABLE MENTIONS: Niall Eccles (one sketch from Fan Expo Canada in 2011: Blue Jay in Toronto), Bill Ellis (six sketches), Steve Ellis (two)