The four cups represent the four dangers from which we were saved: physical, spiritual, lack of connection to history, and a lack of connection to hope. In order to merit redemption we had to take a proactive step in each of these areas. Chazal say that we were redeemed because of four merits.
Delivered at the OU Israel Center, April 14th, 2019, 9 Nisan 5779
This shiur is sponsored by Mel David