Second times the charm. Tested out a few things and then determined that the following steps would result in cider goodness:

Put apples in bucket.

Take 2x4. Smash apples with end of 2x4.

Pour mashed fruit into the cider press and press.

Jeremy and I managed to press about 15 gallons of cider tonight. 10gal went into carboys so it could start it's lovely fermenting. The rest we put into our fridges to drink now. Very very yummy.