This post is made in partnership with Affirm Press.

The Trump administration has a… unique approach when it comes to managing their message. From Spicy, to the Mooch, to SHS, to Kellyanne Conway, we’ve seen a procession of people loose with the truth and creative with their language.

But would an Obama staffer do any better? I mean… they had Obama.

Well, Pat Cunnane was president Barack Obama’s senior writer and deputy director of messaging at the White House where he worked for six years in many roles, responsible for writing statements, jokes, op-eds, and more in the president’s voice.

We asked Pat how he would approach the following briefs to the Trump administration’s greatest misses.

Crikey: Trump sent Sean Spicer out to back up his assertion that there were 1.5 million people at his inauguration. Spicer will forever be known for his angry assertion “This was the largest audience to ever witness an inauguration, period.” Is it possible to top this line of comedic genius?

Pat Cunnane: They started big, like a circus starting with the grand finale, but kudos to them for trying almost daily to top themselves — from falsely claiming 3 million people voted illegally, to decrying the legitimate Russia investigation as fake news, to dubiously asserting the President is the healthiest President ever.

Like some of the best stand-ups, they know how to go big. But, lately it seems they think joking about a national hero’s death is funny, so I fear they might have lost their comedic touch.

There are some many people “transitioning” through the Trump administration that you almost don’t need to announce each one. Could you supply the President a template to use for every occasion (extra points for covering every possible misdemeanor)

Today [NAME] departed the Trump White House to spend more time with [his/her] family and it definitely doesn’t have anything to do with [INSERT SCANDAL].

Or, Fox News could just do a press release each time they hire a disgraced Trump staffer.

Obama was well known for poking gentle fun at Joe Biden. What would you do if set free to “gently” mock Mike Pence?

Gently mocking Mike Pence is too easy, from his musings on the dangers of the Disney movie Mulan to his self-imposed rule that he should never be alone in a room with a woman other than his wife.

What I’d like to see is a movie where Trump and Pence fall into the South Lawn fountain or something and go full-blown Freaky Friday, switching bodies. It’d be fun to watch a homespun nerd like Pence try to antagonize the world on Twitter and a serial-philanderer like Trump try and exist within the confines of the morally stringent Pence household. In fact, I think this is the premise of my next book.

Kellyanne Conway was criticised for penning the term “alternative facts”. What would you have called them?

I think “non-evidence-based truths” rings slightly more scientific. But, I also think I’d have a hard time labeling them as anything other than what they are: lies.

Pat Cunnane’s memoir West Winging It is published by Affirm Press.

Peter Fray

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Peter Fray
Editor-in-chief of Crikey

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