The vehicle is a 79' Dodge B300 Extended Cargo Van. Powered by a LA360 5.9 V8 2bbl 2210/2245 Holley carb. Tranny is 727 freshly rebuilt.

So I recently rebuilt the tranny on this thing and drove it for the first time in about a year and it drove great for about 20 miles and then CLACK! the driveshaft was dragging... When I installed the driveshaft I didn't put the clips in the caps that get clamped. That was completely my fault and was able to get that fixed.
So I got the driveshaft hooked back up and thought I was good to go...

I cranked it and it wasn't starting, it finally started but was running rough and died after about 5 seconds... I cranked it again and it started backfiring out of the carb. It wouldn't start again and I ended up killing the battery which apparently was no good anyway...
I noticed the carb was leaking all around the gaskets so I took it off and tightened everything I could and it still leaks. It won't start at all now! I've removed the carb for a rebuild and ordered a Carter rebuild kit.
Could this be a carb issue? It's obvious the carb needs a rebuild either way...
I checked the spark and the ignition seems good...

What the heck is going on with this thing??? Please help!

Check your timing and compression. The chain may have jumped. Also check that the didtributer cap hasn't been knocked out of place.

Jumped chain is pretty common for a high-mile 360LA.

Hold you hand over the intake manifold where the carb mounts and have a helper crank the engine. There should only be suction during cranking. If you feel air puffing up through the manifold the timing chain jumped or broke.

Disable the ignition and plug or disconnect the fuel line going to the carb so fuel doesn't squirt out.

The motor was rebuilt about 20,000 miles ago before I bought it. I also just replaced the water pump and while there I inspected the chain and it's in brand new condition! Barely any play at all!
The cap and timing are good.
I'll be doing the test that 'Powerflow' suggested today...



,

Sounds to me like your carb is flooding, most likely caused by dirt in the needle seat or stuck float or too much fuel pressure. You have probably gas fouled your spark plugs by now. Rebuild the carb, put in new spark plugs and you'll most likely be ready to go.

Had a buddy loose a driveshaft before and it shook so bad the advance plate in the distributor came loose and it done the exact same thing.

Gus

it is easy to jump to conclusions when multiple things appear to fail all at once.
just because they look related doesn't mean they are. And somethings just happen to fail.

Fix the carb first. Then see how it acts.
in the meantime you can verify tdc if you didn't already.
if the carb went bad like it sounds like, you are just hurting yourself trying to trouble shoot with a broken part.

It was the trailing end of the driveshaft and it just made clanking sounds and dragged a little ways...
I was doing about 75mph when it happened! Had it been the front end I might have flipped it!

The carb has always been an issue and was planning a rebuild anyway. I can't afford a new one at the moment so I'm going to rebuild and hope it works. I ordered a Carter rebuild kit...

The carb had fuel seeping out of almost every gasket even after tightening all the screws... There is still a good amount of fuel that squirts out though...

Already have it off the engine and ordered a Carter rebuild kit... I hope it's a good kit, I had a choice and decided to go with the Carter...
It has positive pressure down the intake if that helps eliminate a symptom...?

I pinched the line and did the test directly over the intake port(carb off). 100% positive suction! So that eliminates the chain correct?

Thought you said you had a Holley?

After you fix the carb, you will probably need to replace the gas soaked spark plugs, and change the oil and the oil filter.
Sounds to me like the float stuck open in the carb and flooded everything with raw gas. The plugs are likely not any good anymore, and gas has been dumped into the cylinders and has probably contaminated the oil as well. Since you have been cranking the motor over, you have pumped the gas contaminated oil into the oil filter and it now has also been contaminated.

Your repair order should be:
1) Rebuild the carb.
2) Remove the spark plugs and crank over the motor for a few seconds with no plugs in it.
3) Shoot a couple of pumps of oil into each cylinder and spin the motor over a couple more seconds.
4) Replace the spark plugs. be sure the plug wires are correctly installed.
5) Change the oil and the oil filter.
6) Start the motor and watch for oil pressure.
7) Adjust the carb.
Gene

That's right... apparently Carter makes a rebuild kit for the Holley and so do a handful of other names...

Interesting, since Carter went out of business in the 80's. Wonder who resurrected the name.

Sounds like the timing chain is OK.

This is all maintenance that was due anyway... It has been about 5-6 years since I bought the van and when I did I replaced the head gasket and "rebuilt" the carb but what I really did was clean it well and change the gaskets. I have always had a problem adjusting one of the needles but always got it to run well. I also have always had a stalling issue when giving the pedal a quick press when in reverse, maybe a carb issue? Who knows but either way that list looks good! Thanks.
The good thing is I already have a box of oil and a filter.
The rebuild kit is on it's way and now to pick some plugs up at AutoZone.
Any recommendations on plugs? It's a stock vehicle pretty much...

They are alive and well at https://carterengineered.com
Seem to be focusing on fuel and water pumps. Iast I knew all was still manufactured in the US
the following might be an answer to your question

technicalhotline@firstbrandsgroup.com

Maybe it's old stock not sure... It's off eBay...
I had a choice between Carter, Tomco and Pronto...
I read Tomco has some fitment issues but couldn't find anything in Pronto... I read that Carter made some good stuff and had been around for a while so I decided to try them. The last kit I bought was a Walker and only used the gaskets... I was really green when I did the first "rebuild"...