Timing gear won't sit all the way in can't put on timing chain

Hello everyone. I have my engine on a stand I am putting it back together after piston and piston ring update. Last night I got the chain on just fine. I took it off this morning because I thought my oil pump timing was off (I'm not convinced it actually was) now that I'm trying to get the timing gear back on to put the timing chain on it just isn't going in all the way. There are 2 keyed lines the back one (the one the oil gear sits on) is higher than what the timing gear keyed hole can clear. What is happening? Something about this is not right and I can not find a single answer online. This picture is as far as it will go.