I vote for a headgasket or a corroded head.  I have seen the latter happen before.  Does it have a stock iron intake, or and allumimum one like Edlebrock.  I have seen those eaten through as well.  I might consider one of the latter issues as it sounds like you have a pretty good size leak and head gaskets are usually not that excessive..
 

Last edited by boomyal (4/26/2015 6:35 PM)

It Has a factory Cast Iron 4V intake the Motor is a 1966 289 A code 4V with A/C  Here is a picture of the cylinder that has the antifreeze pour out of

Bummer. If it were mine I would pull the head and get a close look at the head and the block. If all checks out pull the other head ad get a good look at it just because. And put her back together with new gaskets and be on your way.
L8tr

I'm probably wrong (as usual) butt since you have to pull the intake first, carefully check the gasket between the water jacket and the intake port of that cyl. If not that then back to the head gasket. I would be very surprised if the connecting rod was not bent. Engines don't usually do a very good job of compressing liquids without bending something/

gotstang wrote:

It Has a factory Cast Iron 4V intake the Motor is a 1966 289 A code 4V with A/C Here is a picture of the cylinder that has the antifreeze pour out of

If I am seeing the picture correctly, I see coolant on the outside of the head.  If so, I suppose it could be leaking out between the exhaust flange and the head but a machine shop will pressure test the heads to make sure there are no breaches in the cooling passages.  And yes, you do not have to open up the A/C system, just unbolt the compressor and move it to the side,
 

at- With all the Plugs out and the coil wire disconected the motor spins over fine no funny noices so I dont think I bend anything

First thing I would do is get ahold of a cooling system tester, fill the radiator with coolant and then pressurize the radiator, you may get some idea how bad the leak is and where it is coming from. 

Steve69 wrote:

Lil' Hoss wrote:

First thing I would do is get ahold of a cooling system tester, fill the radiator with coolant and then pressurize the radiator, you may get some idea how bad the leak is and where it is coming from. 

Good Idea Duane!    O'reilly's you can use one for free.  Just put in on the Credit Card and Bring it back in 48 hours.  They'll credit your card back.   That should point you in the right direction instead of Guessing.   Steve69
X3!! It could just end up being the intake leaking into 1 cyclinder. Ask me how I know

 

Don't know if you are a wrench guy- but if you are pull the heads and have them plained a couple thousands, get a gasket set and reinstall. Same thing happened to me a couple years ago. I spent a lot of time trying to figure how it could happen and a lot less time actually fixing it. Good to go ever since!

The bent rod scenario would be my worst fear.  If you hydraulically locked the cylinder due to a slug of water being in it, the rod, piston, crank assembly might need to be investigated.

I will keep You's up to date on My progress with the  head gaskets and reinstalled heads after I get a machine shop to plain them and valve seals and maybe a valve job also

Last edited by gotstang (4/27/2015 5:17 PM)

Brents65 wrote:

Now would be a good time for A set of aluminum heads, cam, aluminum intake etc!

Agree , Or just ah set of 65- 289 heads, they have a much smaller combustion chamber. Those 302 heads are stealing compression from yah. Starting in 66 they made the combustion chambers larger for better fuel economy.