I can only guess you've hit a bend or defect/damaged area in the pipe. For example if there is a 90 degree elbow in there, those can be tough.
Unless someone else has a better idea I can only think of three ways to proceed here.
1. Pull new light wiring back into the pool end. I'm not sure what you might do to lubricate better and get it to budge. As hard as you pulled it could be really wedged in. If you can get it back out you'll need to get a Fish Tape. Amazon has a whole category for fish tape. I'd go with cheap personally. If you are still stuck, you might also get a borescope and hook it to a laptop to see what's going on in the pipe. Obviously there's some expense here. It will probably a lot of finagling and patience. Your local home improvement store will have fish tape and probably a borescope but you'll probably pay a good bit more based on what I've seen in my local area. You can get both a fishtape and borescope for around $30+shipping on amazon.
So assuming you get the new wiring out, push the fishtape through from the end near your junction box. Clean the end of the new wiring and smooth it out as best you can. Lube the new wiring up. Attach the wiring too the fishtape, and use the tape to attempt a new pull. The fish tape should be sturdy enough to push down. It may take some time to push all the way in, and might be a good idea to lubricate on the way down.
2. Hire an electrician to attempt to fish for the line for you. If the conduit really is broken you may end up at option 3 anyway.
3. Dig the conduit up where you think the sticking point is. Clear whatever going on (maybe replace a section of conduit). It could be a root busted the conduit, or someone's got some really bad angles in the conduit. If you dig, do yourself a favor and call your utility companies to come and mark lines in your yard. Hitting a live Electric or GAS line would be dangerous. Hitting buried comm wire could be expensive or at least a big inconvenience.
There was likely a copper bonding wire in that conduit with your light wiring. Did you remove that? If not, try removing it, and pulling it back through along with the new wiring using option #1
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