Sad sooooo very sad!
On the upside I think you should keep harping on the 1918-1919 if he is truly ignorant...... tell him you found a copy of "The Finished Mystery" on google books and really don't see why such a publications would cause Jesus to hail the Bible Students above all others at the time. Then maybe suggest a future discussion regarding selected chapters of that book and what Da Judge and Co were upto then in comparison to today's understanding........why take that long to refine things if the end has consistantly been imminent!
Yes the RCC is a favorite harping subject but his arguments are dated! Yes they were heavily into Mary Worship (like we were in Pyramidology) back when my grandma was young but today's Catholic Church offers weekly bible studies like most Protestant denominations! While I don't agree doctrinally or organizationally with the RCC I still have some in my family and husband's family....... all are far more universally charitable then JWs.
Yes in reality the WTS became a miniature wannabe of the RCC..... but really don't all hierarchies have that in common!
You never know.....he probably has doubts and you might be the one to give him 'permission' to consider them via researching for topical discussions with you!
Maybe you could burn him a CD of collected older pubs from JWN!