The early 2 9/16" shot shells were roll crimped....which is a real PITA but tools are still available. Plan on using a drill to turn it instead of a hand crank.
Federals made their Paper Target shell in 16 ga. at one time and I loaded a bunch for a customer by trimming them 3/16" with an arrow saw and 'reconditioning them with a dip in melted paraffin then running a heated steel pin in the case to 'iron' the wax in and solidify the end where it used to be star crimped. I copied a commercial roll crimp tool and ran it in the drill press.
Plastic hulls are considerably more difficult to roll crimp but it can be done. You might have to cut the pillars off plastic wads to make them short enough in some cases.
Federals made their Paper Target shell in 16 ga. at one time and I loaded a bunch for a customer by trimming them 3/16" with an arrow saw and 'reconditioning them with a dip in melted paraffin then running a heated steel pin in the case to 'iron' the wax in and solidify the end where it used to be star crimped. I copied a commercial roll crimp tool and ran it in the drill press.
Plastic hulls are considerably more difficult to roll crimp but it can be done. You might have to cut the pillars off plastic wads to make them short enough in some cases.