What is the implication of Herman Cain “tried to parse the meaning of “settlement” versus “agreement”?

In Maureen Dowd’s article titled “Cain not Able” appearing in the New York Times November 1st issue, there was the following line:

“He [Herman Cain] has contradicted himself even more risibly on his memory of the harassment charges than he has on his abortion position.

At first, he said he wasn’t aware of the five-figure settlement to one woman; then, suddenly, he was aware. Instead of the meaning of “is,” Cain tried to parse the meaning of “settlement” versus “agreement.” He still claims he doesn’t remember the other five-figure settlement to another woman.”

I don’t get meaning of “Cain tried to parse the meaning of “settlement” versus “agreement.”

Of course I understand “settlement” is different from “agreement,” because they’re different words. But what does this line mean exactly in this particular context.

What is the technical difference and difference of implications between “(five-figure) settlement on payment” and “agreement on payment” to a woman for his alleged sexual harassment charge (or liability)?

Why did Dowd say Cain tried to “parse” the meaning of his own words, not saying “he mixed-up” or “intentionally obscured them" or even evaded the question on his charge?

Additional question: What does "instead of the meanig of 'is'? mean? What does 'is' have a particular meaning here?

People often pay settlements when they know they are in the wrong but do not want something to be dragged out in court - you can (generally) think of a settlement as a payment the accused makes to the accuser to get the latter to drop charges.

Thus, settlement often comes with a connotation of guilt, and may not be a word Cain wishes to use. The word agreement doesn't have the same connotation.

Dowd's use of the word parse seems to be rather facetious. Her point is that Cain tried to say that the two words - settlement and agreement - refer to different things, rather than admit that he lied about not being aware of the issue.

The context behind this statement is Bill Clinton's old Lewinski scandal. When asked about what appeared to be a blatant lie to a Grand Jury, he responded with this:

It depends on what the meaning of the word 'is' is. If the--if he--if 'is' means is and never has been, that is not--that is one thing. If it means there is none, that was a completely true statement....Now, if someone had asked me on that day, are you having any kind of sexual relations with Ms. Lewinsky, that is, asked me a question in the present tense, I would have said no. And it would have been completely true.

Since then, arguing about the meaning of the word "is" has become sort of a catchphrase for someone (typically a politician) using supposed technicalities of the language to lie to people. This is often referred to as "parsing the meaning" of words.

The article in question is accusing Cain of doing this.

"Parse" is a grammatical term, which can only properly be applied to a phrase or sentence. It means to analyse which part of speech each word is, what is the subject of each verb, etc., and has fallen out of use since schools ceased to teach formal grammar.

Dowd is misusing it to mean 'equivocate' or possibly 'take a technical, legal point'. The idea is that Cain is saying there is a grammatical difference between settlement and agreement, whereas in fact there is no difference in normal usage. (Remember Clinton trying to say that "I did not have sex with that woman" was technically correct?) It's a reasonable point (you'd have to ask a lawyer whether settlement and agreement were in fact different in this case), but I think Dowd's own imprecision spoils it rather. More generally, please remember that Maureen Dowd's column is neither factual nor authoritative: it is pure comment, and does not claim anything else.

EDIT: I still think parse is misused here, but I see it's a common way of implying Clintonian verbal gymnastics: perhaps the best way to look at it is as a transatlantic difference.

There is another meaning of parse: to examine in a minute way, analyze critically which still does not fit.

More technical is parsing in wikipedia you will find another pointer

Parsing is a common term used in psycholinguistics when describing language comprehension. In this context, parsing refers to the way that human beings, rather than computers, analyze a sentence or phrase (in spoken language or text) "in terms of grammatical constituents, identifying the parts of speech, syntactic relations, etc." This term is especially common when discussing what linguistic cues help speakers to parse garden-path sentences.

I use parse in yet another way - to mean to understand from analysis or interpretation (probably from computer terminology where parse is used in "interpreters parse input to be able to understand i.e. act on it"). In this sense parse can loosely stand for understand or interpret (since it refers to lexical, syntactic and semantic analysis)

Still Dowd's use is wrong, especially with "parse x vs. y." More appropriate would be "parse x as y", but even then it is not the best term to describe what he did.

Interestingly, the Washington Post picks up the same term and uses it in the same way

His strategy of rolling disclosures has found him parsing the definition of a settlement...

and later, quotes

“When you make a distinction between settlement and agreement it sounds...Clintonian, it sounds like you’re explaining, well it depends what the word is, is,” Krauthammer said. “How does Herman Cain end up parsing words in such a Clintonian legalistic way?”

this is better, but still misses the point - parsing does not, for me, fit here. It is not really important how he parses (understands, interprets) the word, but how he used it (it is important how the word should be understood and interpreted by people who heard it).