Bluegill, this friend sounds ripe for the picking LOL.
I suggest showing them what JW's actually predicted about 1914 in Russell's time (Armageddon, Millennium to begin). Then with this false prediction and their other false teachings, show that they could not have "qualified" as Faithful Slave of Wise Virgins etc. in 1914-1919, so they can't be "God's Organization", then or now. Then they'll be ready to hear about all the other sins of the Society. Then they'll exit.
That JWfacts site we gave you a link to is a fantastic place to start.