Chronic Ankle Pain

I have minorly sprained my ankle many times over my 30 years or so and broken it once 15 years ago but I am starting to have increased pain for periods in my left ankle to the point it is becoming problematic.
The pain began about six months ago and seems to come and go, I can only trace some of it to increased acitivity.
Walking long distances could lead to the pain the next day for example but that is not always the case. I work at a job which renders me very sedentery during the week and find these painful periods only occur during weekends which would be times I am more active than during the week i.e. running errrands, more sports etc.
The pain goes from dull aching while just sitting to serious pain “flashes” I like to call them when walking or putting weight on the ankle, again the pain comes and goes sometimes based on activity but can be further aggravated by having my ankle in a pronate position for long periods while driving for example.
When it hurts the ankle is stiff allowing little movement and I feel instability in the ankle, standing on hard surfaces also is painful. It is most stiff before bed and especially when waking to the point walking is extremely difficult and painful during these periods. The trouble can sometimes be helped greatly iceing the ankle often to the point I can get out and play tennis Sunday morning with little pain if I ice it the night before and then again before putting my shoes on the morning before play.
Even after exercise I find little pain and can not trace the causes that bring about the pain only to have it return again next Saturday evening for example.
I am well over 250 pounds so I am sure this can not be helping my situation but I do enjoy normal exercise playing tennis well as well as pick up football and golf weekly.Any ideas?