Once his reputation was of a feared fighter, an American-born extremist who left small town Alabama to wage war alongside Al-Qaeda-linked Somali Islamists and who called on other foreigners to join.
Today, Omar Hamami -- better known as Abu Mansoor al-Amriki or "the American" -- has split from the insurgents, who want to kill him.
He cuts a forlorn figure: homesick, stuck somewhere in Somalia, and telling anyone who will listen about his apparently doomed career path.
"Amriki would like to accept the honour of most wanted list and thanks everyone," he said in a message on Twitter in November following his listing by the FBI on their Most Wanted Terrorists list.
He spends his days denouncing his former Shebab colleagues as corrupt. He refers to himself as the "former poster boy" of the group.
"War booty is eaten by the top dogs, but the guys who won it are jailed for touching it," Amriki says in one message on Twitter. It is a sharp turnaround for a man who once issued rap videos aimed at recruiting foreign fighters.
While the Twitter account claiming to be Amriki's cannot be verified as genuine, photographs posted on it show the 28-year-old posing with automatic rifles, his lank hair held back by a checked headscarf.
One image, shows him riding a cart pulled by a floppy eared donkey "More luxurious lives of the rich and fame-seeking," the title reads..
Another shows him holding a paper sign scrawled with the date as though a proof of life sign that neither drone strikes -- or more likely, Shebab he has fallen out with -- have managed to execute him.
He also chats with Western researchers on extremism and terrorism via Twitter, apparently jokingly asking if they may "ever consider switching sides?"
"I'd miss the music, bikinis and bacon too much," the reply comes from one.
"I see your bikinis and raise your four wives in this life, 72 in next!" Amriki swiftly replied, as gambling in a poker game.
Another message, in reply as to whether he might go to Mali to support Islamist fighters there, Amriki ponders whether they "could use some new raps", like the songs he penned for Somalia.
The Shebab, who once controlled swathes of southern Somalia before losing a string of key towns to African Union troops and government forces in recent months, have good reason to want him dead.
Amriki, reportedly based in Somalia since late 2006, talks of factional infighting between those keen to follow an international Islamist agenda -- such as foreign fighters following Al-Qaeda ideologies -- and those following more Somali nationalist agendas.
He accuses Shebab commanders of betraying the former presumed chief of Al-Qaeda in east Africa, Fazul Abdullah Muhammad, leading to his killing in 2011 in Somalia.
Fazul is thought to have planned the massive US embassy truck bombings in Nairobi and Dar es Salaam in 1998 and had a $5 million bounty on his head.
In turn, the Shebab have accused Amriki of "spreading discord and disunity", accuse him of a "narcissistic pursuit of fame" and have threatened to kill him.
Certainly, Amriki appears gloomy on Twitter, grumbling that there was "still no real beneficial analysis from anyone" after the release of his rambling autobiography posted online titled "The Story of An American Jihadi".
Amriki, who grew up in the town of Daphne in Alabama, was raised by a southern Baptist mother with Irish roots and a Muslim father with a Syrian background.
His autobiography, written thousands of miles (kilometres) from his hometown, details how he came top in Bible school, misses his family, and craves Chinese takeaways, amongst other foods.
"What I would like though is to have a three day visit to see my mom, dad and sister... I often wonder what this whole experience has done to them," he writes in the book, adding he misses his daughter whom he abandoned in Egypt as a baby.
"After going through all the hugs and kisses, me and Dena (his sister) would probably go running around town laughing our heads off and talking about a billion things without ever finishing a conversation," he wrote.
"I'd like to make a round of the restaurants and get some Chinese food, some hot (chicken) wings, some Nestle ice cream, some gourmet coffee and a slew of other foods and beverages."
Amriki describes his arrival in Mogadishu airport and struggle to integrate with the fighters, and his joy at being given an automatic rifle -- which he admits he had at first "had no idea how to use".
Later, when he was still welcome in the Shebab, he receives hand grenades, his experience of which he admits was limited to that of "anyone who had previously watched a Rambo flick (film)".
Amriki, whose closing remarks in the book are that he can now "only pray that Allah grants me a righteous ending".
"I knew that I was going to become a fugitive for the rest of my life when I made that decision (to fight in Somalia), I was well into the post 9/11 era," he wrote.
"Someone seeking a thrill or a hippy's midsummer's night dream doesn't normally consciously burn his bridges like that."