So as I stated earlier I ran it and it didn't shoot water out of the tell tale, so I blew the water jacket gasket.
Took off the water jacket cover and had a look inside to see this:
First modern boat motor so I was not expecting this. cleaned them up to this quality and replaced the gasket.
This is my boat, a 1958 Texas Maid Osprey, and it resides in Texas (ha, ah very funny), when I got it (for 340$) it was in mediocre condition as you can see. The wiring was all done through the 1960 Johnson 40 HP which was hydro locked (was not sold with the boat), so I had to rip out and redo...