Recent news is James Comey’s revelation that President Trump said:

I hope you can see your way clear to letting this go, to letting Flynn go.  He is a good guy.  I hope you can let this go.

The issue with regard to whether this is obstruction of justice is what kind of speech act this is.  Here’s the discussion afterwards (full transcript here):

RISCH: Thank you for that. He did not direct you to let it go.

COMEY: Not in his words, no.

RISCH: He did not order you to let it go.

COMEY: Again, those words are not an order.

RISCH: He said, “I hope.” Now, like me, you probably did hundreds of cases, maybe thousands of cases charging people with criminal offenses. And, of course, you have knowledge of the thousands of cases out there that — where people have been charged.

Do you know of any case where a person has been charged for obstruction of justice or, for that matter, any other criminal offense, where this — they said, or thought, they hoped for an outcome?

COMEY: I don’t know well enough to answer. And the reason I keep saying his words is I took it as a direction.

RISCH: Right.

COMEY: I mean, this is the president of the United States, with me alone, saying, “I hope” this. I took it as, this is what he wants me to do.

The key is to properly interpret Comey’s distinction between “in his words” and what’s not.

To start, directives standardly take the form of imperative sentences.  “Close the window, please.”  Or “Shut your mouth!”.  That’s how you utter a directive in those words.  But we can have other speech acts, given our interpretive devices in context, with directive force.  “It’s cold in here” is a way to request the heat be turned up.  A child uttering the words “I’m hungry” is a way to demand a PBJ sandwich.  And, in many cases, expressing one’s preferences, especially when the power dynamic is asymmetric, is a form of issuing directives.

For example, if I say “I expect you to clean your rooms” to my kids, I’m not just reporting that I have made a prediction, I am giving an order.  Or if someone on my tenure committee says, “I encourage you to place papers in better journals,” that’s not just some ra-ra encouragement, but a statement better translated as: “place papers in better journals.”

Comey clarified this last point — that when the President lets you know what his hopes are, that’s a way of issuing a directive.  Like if I tell my students that I hope that they can get their papers in on time, I’m not just letting them know about my preferences, I’m telling them what do do.  In the service of this, Comey made a jaw-droppingly-awesome historical reference, that to Henry II’s indirect directive to take care of Samuel Beckett.  Here’s Comey’s version:

KING: …. I think in response to Mr. Risch — to Senator Risch, you said he said, “I hope you will hold back on that.” But when you get a — when a president of the United States in the Oval Office says something like “I hope” or “I suggest” or — or “would you,” do you take that as a — as a — as a directive?

COMEY: Yes. Yes, it rings in my ear as kind of, “Will no one rid me of this meddlesome priest?”

The point, again, is that given the context and the cross-categorical pragmatics of many speech acts, it’s reasonable to see how that could be a directive.  Or a directive given with plausible deniability.