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Having Distortion Issues when Speakers Placed in Cabinet

That’s the one that concerned me. Placing a probe on the hot tip and the other on the ground ring should read open.
Correct, you may be narrowing down the real problem.

Can you verify the the switched tip connection (if the jack has one) is NOT connected to the sleeve?
 
There is definitely an issue. Can you post photos?
IMG_7015.jpeg


This is the cab. Only thing I noticed is the angled pieces are not attached to the baffle.

IMG_7016.jpeg IMG_7017.jpeg
 
Yes some pictures of the jack would help.

Again measuring across the + & - speaker lines with nothing connected needs to read open and check it with the speaker cable plugged in to the cabinet but not plugged into the amp.
Maybe the insulating spacers on the 1/4 inch jack have gotten loose and rotated causing a short by letting the solder lugs and wires to touch.
 
You posted while I was typing, what do you measure across the red and black with no speaker connected, it should be open.

The solder connections could be cleaned up some, too much insulation stripped off on the red wire and a loose strand hanging on the black.
I ordered new wire and a Switchcraft so the old harness gets trashed. I was measuring across the lugs as well as the hot tip and ground ring. The speakers are disconnected.
 
The angle pieces must be solidly attached to the baffle, that's a critical vibration reduction bracing mechanism. Glued and screwed solidly. The screws can be removed once the glue cures completely.

The solder joints and stripping look really rough. It's likely that the internal insulating of the jack itself may have been damaged, If your amp didn't have short circuit protection (many older amps did not), it's also possible that the am is damaged. This will depend on luck.

They should look like this. I tried find a picture on the internet but most were about as awful as yours so I had to grab one from my shop:
IMG_2298[1].JPG
 
All measurements were made with no plug inserted.
Ok, then the jack has been damaged.

If you can't solder well, pay a tech $5 to solder the jack up for you. It's money well spent. Also, you will need to check your amps, hope they didn't get damaged. The older protection circuits were pretty ineffective compared with what we have today.
 
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The angle pieces must be solidly attached to the baffle, that's a critical vibration reduction bracing mechanism. Glued and screwed solidly. The screws can be removed once the glue cures completely.

The solder joints and stripping look really rough. It's likely that the internal insulating of the jack itself may have been damaged, If your amp didn't have short circuit protection (many older amps did not), it's also possible that the am is damaged. This will depend on luck.

They should look like this. I tried find a picture on the internet but most were about as awful as yours so I had to grab one from my shop:
View attachment 5285948
The 200S is fine and have been using it with my B-15 cab to make sure.
 
Thanks for following up with the pictures.

Cut the wires off the jack and measure the across the jack solder lugs and then measure across the red and black wires let us know what you measure.

How are the wires spliced together from one speaker to the next?

Back to the cabinet, those pieces need glued and screwed to the baffle.
Lugs no wires is 0.1 ohm. Detached wires, red to black, is open. They aren’t connected to anything.

The top speaker had wires from the jack to the lugs and then a second set of wires to the second speaker.