Natural speed please, thank you very much whoever you are ;)
Dreadful Jack's flag was black, there was an hourglass with wings in the center. There was a skull on the right and a giant squid on the left.
On Grumpy Harry's flag, there were two crossed swords in the center. I think it was to show his fighting spirit. Then, under the swords there was an anchor, maybe because Grumpy Harry loved the sea and was a true sailor!
Scary Bobby's flag was red, there was a black heart in the middle. Under the heart, there were two daggers. On the left there was an arrow and on the right there was a fishbone.