About 16 years ago, I hit my pinky toe off of a doorway multiple times within a short time period. My pinky toe is still swollen/blue at the base of my pinky toe (bottom of foot). What could be wrong?

X-Ray please. You could have a fractured small bone. I suggest you have an X-ray done in a clinic to check this out. In the meantime try to avoid putting direct pressure on the area of this injury. A soft bandage should help until you can get to a clinic. I wish you the best with your health!