Timing, part sixteen.

Even though he's a thug working for a Nazi, Crossbones does have at least one admirable attribute, aside from the ability to take a two-by-four to the head: he's unfailingly loyal to the Red Skull. For his part, the Skull seems to think more highly of Cross and treat him better than another villain, say, Dr. Doom or Lex Luthor, would treat their underlings.

In his first couple of appearances, during the biweekly "Bloodstone Hunt" storyline, Crossbones was a mysterious silent observer. In his next couple, he seemed a little more...whimsical, cheerfully fighting Cap and singing. Later, he settled into his role as number-one thug: brutal, methodical, and with a touch of black humor; although not as much as his boss.

From Captain America #360, "Blood in the Sea!" Written (and plot) by Mark Gruenwald, pencils (and plot) by Kieron Dwyer, inks by Danny Bulanadi. While it might not have been the most dramatic first appearance, Crossbones would bulk up something fierce before his next one.