We can hope this sentence was the result of a botched cut-n-paste, but I'm afraid that it's probably just an egregious example of what can happen when a writers are toothless to murder their darlings.

I suspect Mr F couldn't bring himself to relinquish the word "toothless," and he knew he needed to say that the Syrians were unable to respond, so he suddenly had this bright idea. You get these bright ideas, at 3:00 in the morning. That's why there are editors.

I don't like "toothless" or "helpless" in this context, either one of them -- I would have no preference between the two however. "Unable" I think is the best word to use in this construction. If you're using "helpless" or "toothless" the appropriate construction is, "in the face of the deepest Israeli air raid..." But "unable to respond to..." I think communicates more information and sounds better.

"too toothless to" would work...but that would be way too silly...

toothless + verb inf. is not all that uncommon, although probably used more by journalists than academics.

Jim Hightower described the SEC as “toothless to battle the corporate greedheads.”

And yes, there's also the “too toothless + verb inf.” construction: a governmental agency is described as “too toothless to matter.”

That this construction is too trumpety is the least of its problems.

Nowadays with the quasi-toothlessness of double-decker dentures, you would suppose the metaphoric power of toothlessness would be less than it is.

My favorite citation for “toothless + verb inf.” is from the Vladivostok News, in a letter to the editor:

“I'm sure working with drunk coal dust that is too toothless to publish cockroaches (that is what you said, right?) must be a major challenge, but I do appreciate having something different to read every week. I speak typo fluently”

You're right, now that I've googled (which I should have tried in the first place) I find a few other citations, like "are the White House media minders toothless to prevent outspoken outbursts from the Defense Department?" (from here) and "Thus, the organization remains open to accusations
of appearing 'toothless' to enforce its decisions" (from a pdf file; note the quotes around "toothless," indicating that the author found something unusual about the usage). I still don't like it, though.

Would "too toothless to..." not be correct by definition if toothless had degrees of comparison? Can one can be more or less toothless? Besides, "too-too-to" is an ugly alliteration.

The idea is that Syria has lost its teeth through violence or old age, or that it hasn't teethed yet? A curious choice of words indeed.

aa -- the normal implication of "toothless" in this context is the former.

In that case, does "spineless" imply that one has lost one's spine through age or violence?

And what about "gormless"?

Ah well, "gormless", d'ye see now, that's just a state of mind, something one, haplessly, is: lacking
gorm, or "gaumr" (Old Norse) - heed, attention, the capacity to mind what one's doing...

Yes, but the question is: did one lose one's gorm through violence or old age, or has one not gormed yet?

ditto ones feck.

A hap! A hap! My kingdom for a hap!

I've always wondered about "ruthless".

Ruth left town a long time ago.

This reminds me of the ghasting of the flabber. Is it the result of violence or old age? or is the flabber too young yet to be ghasted?

i think 'ruth' once meant the same as 'kind'. hence ruthless.

I think the thing with gorm is that one does not so much lose it, as fail to acquire it. The gormless tend to be, predominantly, young, lacking experience. Also, one cannot (to revert to the original casus linguae (is that right? my Latin has flagged somewhat since I was last examined in it)) be "gormless to ..." anything. "Too gormless to..." (tie ones own shoelaces, know how many beans make five, etc.), yes.

Today's NYTimes is a complete and utter fraud. So I'm not at all surprised that the rot manisfests itself by "simple" illiteracy as well.