Say it's 1957 and that 265 is not going to cut it and you want something bigger and back then Caddy had the largest GM engines so I presume the parts were made to adapt the Caddy engine to the Chevy 3 speed and maybe Hurst mounts to bolt it in. What I would like to know is are those parts still available new or are there any still floating around,I am thinking about swapping a 57 to 60 ? Caddy engine in a 55 if one shows up that I can afford. Years ago I think I remember one of those small magazines having a article about that swap but I am 1300 miles from home in Sturgis.
The bell housing/adapter will be very difficult to come up with. Cadillac changed the back of the block in '55 and got away from the pattern that was the same as the early Oldsmobile engines. There is no such thing as a factory standard shift bell housing for the '55-'62 engines, and damned few aftermarket ones.
did you look through the old Trans Dapt catalog? https://www.jalopyjournal.com/forum/threads/tech-transdapt-adapter-numbers.78455/ looks like you'd be looking for a KD-25.
here is a modern adapter that was in the classifieds but has sold, maybe they are still available? https://www.jalopyjournal.com/forum/threads/caddy-to-t5-trans-adapter-and-starter.1189480/ edit, I looked at the wilcap site and everything is out of stock? https://wilcap.com/cad.html
these guys have them for the extended bell engines https://www.ebay.com/itm/1926688824...S+wPHWAjnVp7k6566VaHvDeQ==|tkp:Bk9SR6SV_be7Yg
I have a 55 with a nailhead. It has an Offy adapter to the stock 3 spd OD trans. I wonder if Offy ever made one for a Caddy, Don't they still have all of the old tooling? might be worth a call....
The Offy number to get you from 55-64 Cad block to Ford round flatty style bolt circle is 0303. you can go back in time... https://www.jalopyjournal.com/forum/threads/cadillac-331-365-390-trans-what-the-options.20443/
Actually in my area in the late 50's early 60's, Pontiac was the low buck fix for the 265 Chevy. 316 & 347 ci engines plus the hydro found their way into under powered '55 Chevys.
Offy does have all the old tooling still. After about a year of working with a distributor and Offy directly I was able to buy the first Early olds starter change over they had made in decades. They did a small run of them. They may still have some. It took some time but well worth it.
It might not be any time real soon but if I live long enough it will happen,I have one part and will be trying to get the rest but the biggest hurdle is find a 55 I can afford that is not a 4 door.
I am starting to collect engines and parts for future projects but not finding anything decent at a decent price to put them in,might take me a couple years to collect what I need.
Why not stuff a 500 CI Caddy & a Turbo 400 in it and be done with it, and you will LOVE the that torque monster Caddy, and not have to worry about replacing transmissions often...
I do not tear up stuff now,I can make parts live longer then I did in my younger days and I want a old school swap.