Why does Iago urge Cassio to drink to Othello?  

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A large part of Iago's plan involving Othello and Cassio turns on Cassio being dishonored or losing some credibility so that Othello cannot trust him if he denies having slept with Desdemona.  Othello has great confidence in him and if Iago succeeds in discrediting him, Othello will fall further into doubt about everything regarding his situation and particularly his relationship with Desdemona.

So, knowing that Cassio does not handle his alcohol well, Iago endeavors to get him drunk so that he can get him to do something stupid, in this case get into a duel with Roderigo whom Iago has stashed in the wings ready to start a fight.

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