When he popped up in the middle of the night, I would ping him for status updates. I began addressing him directly, ignoring the spokesman claim and addressing him in the second person as if he were Omar. He eventually began to respond in kind (without conceding the point).
I asked him if he had any cards left to play, and if he had any regrets.
"The last card is the last round in the mag," he wrote back. "No regrets. Freedom! Ha ha."
But over the next few days, the bravado faded, leading me to believe he genuinely expected the end was near. I asked if he was worried that al-Shabab would go after his family. He responded simply, "Nah."
He may have been messaging with others as well (then or continuously), but I sensed he was hard up for friends. I started to feel bad for him.
Not sympathetic, necessarily. After all, his story was in many ways the definition of self-inflicted injury. He was hard-headed. When I asked him if he would consider giving himself up, he either ignored me or brushed me off.
But there was an unavoidable sense that there was a human being on the other side of the line, one who could well die in the middle of our conversation.
It weighed on me, and I couldn't quite figure out if that was appropriate, all things considered. We were, after all, enemies, if you asked either of us. I was also dealing with him as a journalist, my role being to chronicle and not get involved.
In response to a question on my public Twitter timeline, I commented that the best outcome for Omar was capture by or surrender to U.S. forces. He responded defensively in a DM, childishly even, reverting to the third person for the first time in days.
"So you want Amriki caught? That's mean."
"Caught seems like a better option than dead to me, but I know you have a different perspective," I replied. "And I can't help but think that your remaining at large is a story that ends with a school bus or an airliner blowing up."
So much for feeling bad for him.
Meanwhile, the host of al-Shabab-friendly tweeters who had come online to hurl abuse at Hammami stepped up their attacks. He fired back at a manic pace and in a manic tone for some days.
"[Al-Shabab leader Ahmed Godane's] takfiiri tendencies are coming out thru the words of his crownies on twitter. Arrest my case," he punned, sounding punch-drunk. He posted a picture of himself on the run from al-Shabab, on a donkey cart, with the caption, "A pic of the lavish benefits of narcissism." He picked fights with terrorism expert Clint Watts, who had written extensively about Hammami in a long series of blog posts.
Soon after the ultimatum was announced, Omar posted two long Arabic texts detailing some of the allegations his autobiography had only obliquely hinted at. He was disappointed in the tepid reaction from the West.
"This proves the USA has a minute capacity in the Arabic-to-English translation field," he grumbled in a DM, after only a few people wrote about his latest exposé. "Also no media strategy for handling Amriki. Silence."
He was piqued people weren't taking his current plight as seriously as the first time he warned al-Shabab wanted to kill him.
"Given this is kind of a replay of last year, I didn't expect much coverage," I responded in a DM.
Our conversations turned more ideological, pushing and pulling over terrorism and the intentional targeting of civilians, the significance of the Arab Spring, and Omar's belief that the United States was oppressing Muslims around the world. We sparred over whether America had a national security interest in the establishment of an Islamic caliphate, one of his pet obsessions. He argued that the United States feared the caliphate; I argued that we wouldn't much care as long as terrorism wasn't the method for its establishment. Just when the conversation would start to get interesting, he would pull back.
I noted that his mood had improved.
"Just a mad man. Nothing new. Ha!"
But something had changed. A local tribe had pledged him support against al-Shabab, he told me. The ultimatum was, for the moment, moot.
"So where does that leave you? Cutting a new rap album? New … book in the works?"
"Amriki isn't that big of a joker now, is he?" he bristled, complaining about my jokes at his expense, as well as humorous comments by Watts. "I think what seems funny now will be seen as the turning point for real change."
His rising megalomania suggested his claim of tribal support might be true.
"The west has a greater interest in discrediting Amriki than the defeated Shabab," he wrote, now thoroughly in the third person. "Call him a diva if you like, but they're scared."
"Now, see, it's hard not to poke fun when you start talking like that," I replied.
I decided to prod Omar with a question about his relationship with another American in al-Shabab, whose house had been used to film his first panicked video call for help.
"I guess I'll call it quits on our 'thoughtful' discussion," he shot back tersely. "The future is ours to see." (I'm guessing he didn't intend to quote Doris Day, but with him you could never be sure.)
I let him go. I was, frankly, exhausted. For almost three weeks, we'd been going at it at high volume. I had been oscillating between feeling the weight of companionship to a man under a death sentence and the frustration of trying to talk with someone who could turn childish and petulant in the blink of an eye.
The break didn't last long. Omar almost immediately began trying to engage with me in public on Twitter (in addition to many others). For an ego of his size, the divided attention of just one person could never be enough. He wanted an audience for our exchanges. I wavered in my resolve to avoid giving him publicity. His account was pretty well known by then, in part because of his relentless efforts to engage people in the counterterrorism and journalism communities.
A certain amount of calculation went into my decision to take him up on the challenge. Bad press for al-Shabab could only be a good thing, for sure, but there might be more to learn from these conversations -- insights to what a Western jihadist believed, what parts of the al Qaeda party line he accepted unquestioningly, and where the soft spots in his thinking could be found.
I began to engage, leading to lengthy public exchanges on corruption and racism in jihadist movements, and what kinds of jihadist violence were necessary, just acceptable, or excessive. Although he sometimes slipped into dogmatic religious justifications, he could be pushed past them -- at one point I told him "'Because God' is not an interesting answer," and he gamely continued on the issues. Eventually, I goaded him into admitting he was not Omar's spokesman, but Omar himself.
Others got involved. For a time, Islamic studies scholar Christopher Anzalone patiently engaged with him to get at the details of his Islamic justifications, which came off as simplistic. On the other hand, Will McCants, one of the smartest and nicest people studying the ideologies of jihadist extremism, had less patience for Omar's posturing. After being dragged into the conversation by a third party on Twitter, he dismissed Omar sharply: "I've got better things to do than listen to your Milestones talking points. Enjoy your 15 minutes."
Online jihadists were irked that Omar was speaking with the enemy so freely. After one of several such challenges, one of them tweeted, "The only reason (they) are even talking to you is to get more info from you! And to make fun of you, don't you see that?"
"Clint, JMB, and gang... Is this true?" Omar asked.
This was an awkward question and it highlighted my growing internal discomfort with the tension between my work interest in Omar and the fact I was perversely starting to like him, even though I was appalled by his values and the path he had chosen for himself. I had come to enjoy these exchanges as a part of my routine Twitter life. But I had also exploited the information he had provided in ways large and small, including finding ways to surreptitiously keep tabs on whether he was alive during his periods of long silence.
I answered at some length, honestly, but with very carefully chosen language, concluding, "If you sent me your GPS coordinates or terrorist attack plan, it would complicate my life, so please don't."
Clint Watts was characteristically more direct.
"For information, yes, of course," he tweeted, listing some of the various ways he used that information.
"Yeah, I thought it was a fun dramatic question to ask," Omar replied. "I'm a grown-up and know who I'm dealing with. Good answers though."