Ok, I am big into working out and diet stuff. Always thought it would be cool to be a personal trainer, but I chose Science instead. So I help my friends out on the side. Plus I have learned alot about diet/exercise through working at GNC and boxing.
As far as the diet goes I would try and do the atkins thing. I know a lot of people talk shit about it but it works. I had to make weight for a fight once and I ate no carbs for a week and lost about 10 lbs. Granted I was jogging and doing my work-outs still but hey it was still 10 lbs. I just ate straight protein the whole time. Basically you can eat anything ya want except stuff with bread. I ate chicken, burgers, and vegetables. Mostly meat though. No rice/bread or anything like that. It's not a lifestyle, just a way to cut off some weight and get the ball rolling.
Now as far as the exercise thing goes there is a big misconception on the cardio thing. Cardio is great for burning calories AT THE TIME YOU ARE DOING IT. However, thats like a mental fix. What I mean is, people go in and do cardio and feel like they really did something. Which is good, however what you want to do is burn calories around the clock. For guys this is pretty easy. What ya want to do is increase the amount of muscle that you have. We do this by weight lifting. See, throught evolution our body sees muscle as the enemy and fat as our friend. This is because it takes a lot of protein and food to power all that muscle, even if you aren't doing anything. Whereas fat helps us out if there is a shortage of food by providing extra nourishment for the body, muscle just uses up extra calories. So if you can increase the amount of muscle you have your body will burn calories around the clock ultimately causing you to burn way more calories per day then doing a couple hrs of cardio a day. You can go to a gym/fitness club and they can usually tell you your body fat percentage and your amount of lean muscle. With that they can estimate the amount of calories you burn a day if you just laid in bed and did nothing, basically how many calories a day your muscle is consuming for simply existing. Last time I had mine checked they said I burn 1200 calories a day from doing nothing, so you can imagine that it's quite hard for me to put on weight.
So what do I suggest? Well you said you benched 250 at 180, which means you were reasonably strong at one point. What I think you need to do is start lifting again. For maximum results I would lift 5-days a week and after each work out session you could jog, stair-step, jump-rope, or use an elliptical trainer. For instance, on mondays I would do bi's & tri's (GUNS), Tues- Legs (whatever you wanna do), Wed- Chest (do flat, incline, & decline EVERY TIME, if you skip one you have to do butterfly's/pec dec/or cross-overs), Thurs- Back and Shoulders (I like doing Arnold presses, behind the neck presses, widegrip chin-ups/lat pull-downs and rows), Fri- Do extras, thats what I call em. Do like, calf-raises, fore-arms and sit-ups. Perhaps some cardio here and I work out guns again simply because no matter what the rest of your body looks like if you have a big bicep/tricep and flex most people will be impressed. Also in boxing it's good for intimidation and I happen to have good genetics for arms.
So... there ya have it. Thats what I personally would do. I have had quite a few friends foolow my advice and it worked for them. But remember, you're not going to lose weight unless YOU want to. Nobody can force ya to do anything. You have to get to the point where ya feel terrible if ya miss a day. I always think that if I miss a day its gonna cause me to lose my next match. That keeps me motivated. Plus when ya go swimming or play volleyball and ya take your shirt off for the first time in the summer, its all worth it.