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The bottom end of the distributor drive gear is flat and fits into a slot on the oil pump drive. So it only fits down that last 1/3rd inch or so when it slots into the oil pump.
What can work is pulling the gear up enough to disengage from the camshaft gear, turn the motor around some, then dropping it back down to reengage with the cam gear, then turning the motor around that other 90 degrees until the oil pump slot lines up again.
It takes some light downward pressure on the gear as the motor turns. If you push down too hard, the shaft can turn the oil pump even though the slot isn't engaged, so just a little light pressure.
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'63 PV544 rat rod, '93 Classic #1141 245 (now w/16V turbo)
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