Toro SS4225 42 inch deck.

Need to look at the lift system. works like a hinge. and pins. Something isn't align right, or something is jammed. Pretty basic system. Keep looking and you'll figure it out;
 
Have you released the transport lock ?
On the height adjuster there should be clip of some sort to stop the height adjustment lever bouncing out when trailering the mower.
 
Timecutter does not have transport lock, just the 4-1/2" range on stick.

To OP: Suggest you set height handle to lower setting 3" or below & wiggle the deck, it can get stuck up high.
 
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