1st gear poping out and grinding

[cudvig]

So I sold my car to my friend. The car shifted fine when sold. It slowly started grinding 3rd and then 2nd and 1st. Now it won't go into 1st gear. It also pops out. The clutch has about 6k miles on it. The tranny is leaking some fluid. Not sure exactly how much it has leaked already. We are going to put some tranny fluid into it and then try again. Do you think anything else Could be wrong with it? Will he need a new transmission? The leak is near the transfer case and its not the axle seals because they are new also.

thanks in advance

-Colin