My roommate was having problems with his 69 442, The car is hesitating and knocking/tapping from underneath the car. I put a stethoscope on it and it was coming from the tranny(stock turbo 400). I heard a squeal and a tap from the pan/tailshaft area when turning the driveshaft by hand. I pulled the tranny pan and found shavings, not good. My question is- Is there supposed to be a hole above the throttle linkage, or did something break though? Thanks guys!
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That doesn't look like factory to me. Take the pic to a trans shop.

 

Hole in the tranny case, not a good thing.

New/old cases for the 400 are a common thing. My 68 th400 tranny didn't have a speedo provision, so I got a new case in the rebuild. It was all of $75

Question: How did he do that? I put a square hole 2" x 6" in my Alero's 4T45 tranny and still drove it for a week. It was right at the TC. 3 years of launching the car at 2500 RPM's didn't fair too well

 

Actually, it's difficult to tell from the photos. I've seen several instances of holes in the casting due to incomplete fill in the mold. These are in non-critical areas and are acceptable. You'll need to perform a closer inspection to tell if the edges of the hole were actually fractured or if this is just casting flash. Also, you should have recovered the missing fragment in the pan if it were really a grenading part.

 

Looking close at the pictures it looks like heat stress cracks are all around the hole with dark discoloration. Did the tranny fluid smell burnt and was it dark brown in color. Lots of hard use with no care can cause heat fractures in the alumimum

 

You got that from a couple of somewhat out of focus pictures? I wouldn't read too much into those photos. The "cracks" are pretty typical of normal cases I've seen and are the result of the casting process. The discoloration in the cracks is also pretty typical.