[Winga]

Why weaker the base, better the leaving group?

[Donaldson Tan]

i would tend to think weaker base in the sense that it would be less reactive, thus indicate higher stability to act as a leaving group

[dexangeles]

less basic --> less nucleophilic --> better leaving group

[Winga]

But, less basic doesn't mean that it must be less nucleophilic, right?

[Mitch]

Maybe its because you don't want to encourage the competitive reaction of elimination.