Mustang won't run

I am looking at a friends '66 mustang with a 287, this car quite running about a week ago and I went over to try and help and take a look at it. The car was getting fuel just fine, so I pulled a spark plug wire and there was no spark, so I pulled off the distributor cap to make sure there was no crack and to look at the rotor, when I rubbed the end of the contact the rotor just spun freely. So we pulled the distributor and the roll pin running the drive gear had sheered. Everything inside the distributor slot looked OK, so I put in a new roll pin and all seems to bo okay but the new problem is timing the car close enough to correct to get to run. We put the engine on TDC on the timing mark, and put the rotor lined up to the #1 cylinder point. No luck on starting so I was thinking that we might be 180 degrees off so we rotated the rotor 180 and still didn’t have any luck, any suggestions would be helpful

Well, first it’s a 289. The 287 was found in Ramblers of that era. Are you sure you’re not working on a Javelin? No, not if it’s a '66. AMC didn’t join the pony car craze until '68.

To be sure that you time it up correctly, pull the #1 plug and bump the starter until you feel the air for the compression stroke push your thumb away from the plug hole. Then point the bug at the #1 position on the distributor cap. You could easily be one plug wire off too, it doesn’t take 180 degrees to not fire at the right time. Even after stabbing it this way, you will still need to turn it some to reset the timing with your timing light.

What do you suppose caused the roll pin to shear? Might there be a bearing problem in the distributor? If there is any side to side play in the shaft, the points can open and close at undesired times. Might the points just be loose or incorrectly set? If the bearings are bad enough, that can also damage the rotor bug and cap, but you checked those.

sorry about that it is a 289 been a long evening, it is an aftermarket distributor, the bearings in the distributor seem to be in good condition, they spin freely. I’m not sure what sheered the roll pin exactly, there doesn’t seem to be any slack in the shaft, I’m not that familiar with this newer style of distributor, there are no points or condensors. It says that it is an ignitor 2. I will pull the #1 plug and go from there, any suggestions on the best way of turning the engine by hand to get it at tdc or is it best to crank it with the starter

There’s a lot of unknowns here but some possible causes of a sheared roll pin on the dist. gear could be:
Binding dist. shaft bushings due to heat or lack of lubrication (that’s what the little holes in the housing are for), oil pump seizing up (unlikely), cam seizure and dist. drive gear stripped, wrong gear for the application, etc.
Is it known if this engine has been modified to use a roller cam? The steel gears will not last long with a roller cam.

It would help to know exactly what kind of distributor you’re using, whether the engine is even coughing or spitting during all of this, and I’m also assuming the rotor is now turning after the roll pin replacement. The fact that roll pin sheared would make me wonder about the underlying cause though.

You should also make sure that you have power provided to the coil and/or dist. when the key is in both the RUN and the START position. Maybe you have a bad ignition switch.

After that I would say remove No. 1 spark plug, bump the starter while placing a thumb on the plug hole, and stop the instant you feel air blowing out. Rotate the engine by hand to TDC, align the rotor at the No. 1 cap terminal, and drop it in. It should do something at that point, IF the ignition switch is providing power as it should.
(Since it’s unknown what kind of dist. system you’re using it’s also possible that it uses a resistor block or wire in the circuit and that resistor has failed. Checking for power as I mentioned should verify this.)