Well one of the tanks is cracked and we have 2 jacks, one large and one small, then 2 oscars, both kind of small. Would it work if the fish were put together, or would they fight / kill each other?
Jack Dempseys are as wimpy as Oscars and much more shy, what size tank are you putting them in?
Yes Jacks tend to be "wimpy" compared to other more agro cichlids but against smaller Oscars it could easily be a bully. Especially if you have a male and female Jack. Ive had a 9-10 inch JD eat a 5-6 inch tankmate before so dont just write them off as kittens.
It will depend on your tank size and fish size IMO.