Head Gasket? or worse

[300EforERIC]

SHORTER VERSION: Car ran hot, Changed radiator and oil. Oil came out a mocha color, And now new oil is the same color off the dipstick. Exhaust spews White smoke and now wont start.


LONGER VERSION: I recently had overheating problems on my 1991 300E 3.0 Liter. After searching and searching for the coolant leak, I found it. The side of the radiator had cracked so I ordered a new one right away. This is my only car so I made a few trips to town with this leak always carrying a jug of water along with me and topping it off before every trip there and trip back. So my car ran a little hot a couple times once the water ran low and i was nearing home. So I got the new radiator yesterday and after work I put it in and flushed the system with plain water then put in the Antifreeze.

I knew my Engine had run Hot so i changed the oil too. It came out a weird Mocha color. Like a cup of coffee with two creams in it. I didn't know what to think, I had never changed my oil that soon nor had I done so after running hot. so I changed it and now the car runs horrible, spews white smoke (which smells horrible). And I checked the dipstick. the oil is the same mocha like color. Even after several wipe offs.

Any Ideas?
Thank you.