You have either a broken reed valve on the valve plate or a broken piston ring and/or badly scored cylinder. To check: remove the head on the air pump, the valve plate is directly under the head. The reeds have to be in good condition, no breaks, cracks or bending, to work properly. If they are OK, check the cylinder, it should be very smooth. You will have to remove the piston to check the ring around it. They have a tendency to dry out and sometimes a small section will flip over backwards and will no longer seal the piston enough to compress the air. You'll have to contact Sears to see if parts are still available for this compressor.
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