Are political deals legally enforceable if they are in writing?
For example, let's imagine a candidate makes a deal with a political party: "I agree not to run for office in race X right now, if you agree not field a candidate against me in race Y which is coming up next year and promise to pay me an indemnity of $500,000 if you break the agreement and run in the race anyway."
One of the things required to make a “deal” into a contract is legality of objects. This means that a contract that requires lawbreaking is illegal but so are contracts that contravene public policy. Interfering in the electoral process definitely contravenes public policy.
Not to say that such deals aren’t made and honoured all the time, just that if they are breached a court won’t enforce them.
I don't believe that you could enforce such a deal through a court case. I have never heard of one being so enforced. However, someone who breaks such a deal is likely to harm his or her reputation among political insiders, and find future deals very hard to obtain.
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