1 Three years into his presidency, Barack Obama shed his first tear.

In Grace: President Obama and Ten Days in the Battle for America, out October 4, author Cody Keenan, a Chicago native who was 44’s chief speechwriter, recalls Obama striking a first draft of a reaction to the 2012 Sandy Hook school shooting. Its language placed the president in the shoes of the dead children’s parents. “Too raw,” Obama told Keenan. “I wouldn’t be able to get through that.” He struggled to deliver even the revised version. A minute in, he wiped away a tear, stared at his papers, and blinked for 12 seconds.

2 Sandy Hook left Obama jaded.

Victims’ families advocated background checks for all firearm purchases, but Republicans blocked it. Following that, Obama told his staff he didn’t want to speak after another mass shooting: “What am I supposed to say? ‘Well, we tried; we’re just not going to do anything about this anymore’?” Three years later, when a white supremacist murdered nine Black parishioners in a Charleston, South Carolina, church, Keenan helped prepare a response for Obama focusing on the country’s ability to change its nature, rather than on gun control.

3 The iconic “Amazing Grace” moment almost didn’t happen.

Obama didn’t plan to speak at the funeral of the Reverend Clementa C. Pinckney, killed in Charleston — until a push from senior adviser Valerie Jarrett. Keenan had put the words “Amazing Grace” in the eulogy. Obama added all the lyrics, telling Keenan he’d sing them “if it feels right.”

4 Speechwriting can mean no sleep.

In one 48-hour period in 2015, the Supreme Court ruled on Obergefell v. Hodges, legalizing same-sex marriage nationwide, and King v. Burwell, upholding the Affordable Care Act’s tax credits. Keenan had to prepare four speeches on the marriage case and three about the ACA. He slept three hours during those two days. On the ACA defeat speech, Obama wrote, “Didn’t need this, brother!”

5 Obama didn’t tweet himself.

He dictated tweets but, unlike a recent president, never hit send. His staff reviewed them first. Still, Obama had final call. After the Charleston shooting, he proposed quote-tweeting Mitt Romney’s call to remove the Confederate flag from South Carolina’s capitol (“Good point, Mitt”). Staffers worried it could backfire with Republicans. Obama insisted.