Disclosed are cloud point depressants and methods of making and using them. The disclosed cloud point depressants comprise copolymers of a maleic moiety polymerized with alpha olefins and then contacted with an aliphatic tertiary amine to provide a cloud depressant reaction product. When the disclosed reactions products are added to middle distillate fuels or blends of middle distillate fuels with biodiesel, the cloud point depressants inhibit the precipitation of waxes and/or biowaxes in the fuels and the fuels exhibit reduced precipitation, gelling, and/or crystallization when subjected to low or cold temperatures.