you need to define the submenu’s items in variables if you want to check which item is selected:
like :

function jsocMainMenu(menu)
    --Creates the Main Menu for the Role Select
    local roleSelect = _menuPool:AddSubMenu(menu, "Role Select")
        menu:AddItem(roleSelect)
        --This is the Role Select Sub-Menu (Rifleman, Auto Rifleman, Medic)
        local first = NativeUI.CreateItem("Rifleman","")
        local second = NativeUI.CreateItem("Auto Rifleman","")
        local third = NativeUI.CreateItem("Medic","")

        roleSelect:AddItem(rifleman)
        roleSelect:AddItem(second)
        roleSelect:AddItem(third)
        --Where the Action would take place within the SubMenu
        roleSelect.OnItemSelect = function(sender, item, index)
            if item == first then
                TriggerEvent("chatMessage", "Rifleman selected")
            elseif item == second then
                TriggerEvent("chatMessage", "Auto Rifleman selected")
            elseif item == third then
                TriggerEvent("chatMessage", "Medic selected")
            end
        end
end
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