locate nail inside and tap loose with nail punch
once nail pops out grab it with pliers and pull
use old nails if possible to attach new handles
Repair the Leather Handles
When buying an antique steamer trunk, inspect it carefully, checking for severe rust or rotting. Trunks with only moderate damage can often be repaired because replacement parts such as corner trim, latches, rivets and leather handles are available through mail-order companies specializing in trunk restoration.
Leather handles, a common problem area on old trunks, are easy to replace. Stain new leather handles with a commercial oil-based stain before installation.
The metal brackets holding the leather handles are often secured with nails that have been bent over inside the trunk. Use a tape measure to locate the nail point on the inside of the trunk lining, then tap it loose with a nail-punch and hammer. As each nail head pops out on the outside of the trunk, grasp it with a pair of pliers and pull it through.
When enough nails have been removed, slide the old leather handle out of the bracket and replace it with the new one. If possible, use the original nails to secure the new handle. Tap the nails in place with a hammer, and bend them over inside to attach them to the wood. If the old nails won’t hold, replace them with new nails or screws.