Dwayne, I thought the same thing and it eventually may. I ran it with the bush hog about 1/2 hour and it didn't make any difference. I just got off it again this time pumping the brake pedals and clutch, cycling the 3 point hitch up and down, and also operating the rear hydraulics. Nothing changed.
I recently bled the brakes on my backhoe, but it is a separate system. I think the same hydraulics on the tractor are used for transmission, clutch, brakes, and steering. The steering seems normal, but no brakes.
I see what may be a bleed valve on top of the axle near the brake line connection, but i wouldn't think you would bleed the entire system through the brakes. I'm guessing the same axle is used in other models that may be different.