Complex sentence: This was accomplished through challenge in the following manner: a challenger would ask to see the medallion, if the challenged could not produce a medallion, they were required to buy a drink of choice for the member who challenged them.
Split into simpler sentences: This was accomplished through challenge in the following manner: a challenger would ask to see the medallion. If the challenged could not produce a medallion, they were required to buy a drink of choice for the member who challenged them.