I have had several bouts with heal bruises. They heal very slowly. I would suggest heal cups for his shoes. They have some that you can actually form to the heel and cut out an opening (think like a doughnut) that the bruised section of the heal can be cradled in.

Not sure if its the same thing, but I had something similar. My heels would become very tender to the point it was hard to walk on them. I went to the doc and he said I needed to stretch more. The one stretch he said to do was face a wall put both hands up against the wall (like your going to push it) and have one leg forward and one leg back (like a sprinters start just not down to the ground). Then stretch for 30 secs and switch legs. Do 2-3 times a day for a week.

It worked for me. Not sure if it was the stretching, or just the waiting game that allowed it to heel on its own.

Hope this helps.

PT, sounds like an ortho problem at first flush to me. Have you ruled out plantar fascia, tendinitis of the many muscles the run around the side of hte foot and attach under the heel? Any PT worth their salt will touch his foot, make them walk about, look at how his foot moves, evaluate how he uses it, ..... on and on and on...

sounds like it needs an xray or MRI.... and I would bring him to a doc to examine the problem, by touching it, not someone who will just assume it's stretches...Generally tendinitis and plantar don't cause bruising . The bruise is blood under skin, who knows were it came from, get him checked out.