John deere won’t free wheel

[MJT]

Have a JD 5100 that won’t free wheel very easily, when running down yard with clutch dipped you can notice fair amount of resistance. Jacked up front axle and that’s fine, with backend jacked up you can just about turn the one wheel but hardly move the other,could it be that brakes are on way out or similair ?

 

[Tractortech]

Now Then..
Depending how it's been driven, excess prolonged use will cause heat and distortion. In normal use with good trailer brakes they last forever. Water ingress causes the friction linings to swell, this also causes drag.
Axle trumpets out, and have a look.. New oil and filter when you put it back together..