As mentioned before, BotCon 2014 is featuring exclusive toys centered around a "Pirates vs. Knights" theme. Some fans may be surprised to know that there are, in fact, a few pre-existing "Pirate" characters in the Transformers franchise. One of these was introduced in the Cybertron toyline in 2006: Cannonball, and even when the convention theme was first revealed to fans several months ago, it was pretty obvious that one of the figures in the box set would be a new version of this character. But let's focus on the original for now....
The original Cannonball figure was a repaint of Cybertron Red Alert, with some creative paint applications to give the illusion of an eye-patch simply by painting one half of the figure's head a dark color. After all, what says "pirate" better than an eye-patch? The fact that one of the figure's hands was a Shockwave-like stump probably didn't hurt matters, either.
The addition of a green skeleton on the sides of the vehicle mode also helped convey the "pirate" concept, as well as a design on the top (see the picture below) that evokes (without copying) the "skull" motif associated with the Jolly Roger. While it might be argued that the undeniably land-based vehicle mode seems an odd choice for a pirate character, the deco nonetheless sells the concept well.
Perhaps the most intriguing aspect of Cannonball's character, at least to me, was the bio released for him online (as opposed to the shorter version on the toy package itself) at the time of the toy's release. Basically, Cannonball is the Transformer version of the "Dread Pirate Roberts" from The Princess Bride. While that movie is more than 25 years old now, it was perhaps one of the most universally-loved movies of my generation, and finding a reference like this in a Transformers toy just amuses me more than I can say. I'm pretty happy to see Cannonball given a new lease on life with the upcoming BotCon figure.