^^^ As Bondo asked and if a Mercruiser it should be posted in the Mercruiser forum on this site. Sounds like one of the 2 solenoids usually located on the pump is shot if its a Merc. You can always swap them out to verify.
Stamas' of that era frequently came with MerCruiser sterndrives. If that is what you have, you would normally push the middle and top button together to raise the outdrive all the way.
To clarify. .... the bottom and middle are for when you are in the water. Then to put all the way up in the trailering position you push the middle and up at the same time. This is a safety feature as at a certain up position it hurts the motor to run it that way.
BTW pretty sure i have the same question posted here from a few years back. This was my first experience with three buttons
