Assuming the Association says no, Bennett will have two primary options for getting around the agreement. First, he can go to court and seek a declaratory judgment that states that the "confidentiality" provision is unconscionable, and against public policy, and thus cannot be enforced in the current circumstances. Or, Bennett can simply have his client speak out, technically breach the contract, and then make a similar argument on defense if the Association has the gall to sue the woman for defending her own honor. (Memo to Herman Cain: please don't sing at your deposition).
Whatever "confidentiality" the agreement contemplated, Bennett would tell a judge, it didn't contemplate silencing his client from responding to public comments made by the person allegedly responsible for the problem (and the underlying settlement) in the first place. There is no way to know for sure whether this argument would work -- at a minimum we would need to see the specific language of the Association's settlement agreement -- and courts generally are reluctant to declare contracts unconscionable. But there is a clear legal path to allowing the woman to at least make the argument to a judge.
And there also are several obvious questions we would need to answer. Is Cain an intended third-party beneficiary of the confidentiality provision? Would he be entitled to monetary damages if the woman breaches the contract? And precisely what would those damages be? Would the Association get its $35,000 back? What about Cain? Moreover, just as Bennett could go to court seeking a ruling that blocks the confidentiality provision, the Association could go to court seeking an injunction enforcing it. And if the woman spoke after such an injunction was issued she'd presumably be in contempt of court.
Here from Section 178 of the Restatement (Second) of Contracts is the black-letter law often used when it comes to these sorts of disputes. This is a general standard many judges would apply in determining whether to preclude enforcement of the confidentiality provision in the agreement and I include it here just to give you a sense of what sorts of issues the lawyers now are likely evaluating in this dispute:
Restatement (Second) of Contracts § 178 (1981). § 178. When A Term Is Unenforceable On Grounds Of Public Policy
(1) A promise or other term of an agreement is unenforceable on grounds of public policy if legislation provides that it is unenforceable or the interest in its enforcement is clearly outweighed in the circumstances by a public policy against the enforcement of such terms.
(2) In weighing the interest in the enforcement of a term, account is taken of
(a) the parties justified expectations,
(b) any forfeiture that would result if enforcement were denied, and
(c) any special public interest in the enforcement of the particular term.
(3) In weighing a public policy against enforcement of a term, account is taken of
(a) the strength of that policy as manifested by legislation or judicial decisions,
(b) the likelihood that a refusal to enforce the term will further that policy,
(c) the seriousness of any misconduct involved and the extent to which it was
(d) the directness of the connection between that misconduct and the term.
There may be other legal options as well -- and if there are I hope readers will chime in with their own ideas. In the meantime, in case you are wondering, I haven't seen anything so far to suggest that Cain himself could get the Association to waive the provision. So he gets to take his shots at this woman, and proactively deny her story, while hiding behind the protections contained in the Association's contract. It's despicable. It's unfair. But right now it's the law of the case.