I already cleaned the wheel. I scraped every bit of the old silicone off. I actually took my time to ensure a good job with mineral spirits. The rim has been drying for over 24 hours. I am letting it dry a full 48 hrs before I mount the tire back on. I will let you guys know if it sealed.
I believe what happened is at one point the car must of come down hard from a wheelie with a previous owner. The silicone had a slight tear in it which would allow air to escape from the center of the wheel because it's a three piece design.