Before Douglas McCain left for the Middle East in March 2014, he accompanied his younger brother and two others to a San Diego gun range.
Five months later, the 33-year-old was killed in Syria — the first American believed to have died fighting for Islamic State.
McCain's brother Marchello has denied any knowledge of terrorist affiliations, telling FBI agents that he thought Douglas had headed to Turkey to play music and teach English, according to court records.
Marchello McCain, now 33, has been charged with lying to federal agents about matters "involving international terrorism." Convicted in Minneapolis in 2005 of shooting at two people, he also faces charges of being a felon in possession of firearms, body armor and ammunition found in an apartment and a storage locker.
In a motion filed in court this month, McCain said he was prepared to admit to the gun charges, but cannot admit to lying about what he doesn't believe to be true.
"Because McCain did not [and does not] think that his brother was involved with terrorism, he is not guilty of lying to agents about a case involving terrorism," his lawyer David Zugman wrote.
Prosecutors say the evidence suggests otherwise.
According to Assistant U.S. Atty. Shane Harrigan, the brothers' relationship was close, with Douglas McCain moving to San Diego from Minneapolis in 2005 and Marchello a year later.
Communications evidence suggests that the "defendant and others were aware that Douglas was planning to go to Syria, via Turkey, knew that Douglas might never return and were making plans accordingly," Harrigan said.
On March 7, 2014, $2,600 was deposited into Marchello's wife's bank account. The next day, a plane ticket to Turkey was purchased using her credit card, authorities said. Texts between Marchello and his wife showed that $2,000 of that money belonged to Douglas, who left March 9, prosecutors said.
In the months that followed, Marchello McCain told FBI agents, he spoke frequently with his brother on the phone but Islamic State was never mentioned.
The closest that a conversation came to that was during a call in July, when Douglas and two friends from Minneapolis who also had left for Syria told Marchello they were fighting with a "group" against President Bashar al-Assad's regime, prosecutors said.
In August, when one of the friends called to report Douglas' death, he said they were fighting the Free Syrian Army, Marchello told investigators.
Marchello McCain's lawyer argued in court papers that fighting Assad doesn't necessarily constitute terrorism, since the U.S. also openly opposes the Syrian dictator.
Marchello McCain told the FBI during various interviews that his brother was an idealist and dreamer, was in no sense a religious conservative and would "never sign on to what ISIS was selling," Zugman wrote.
In his motion, the lawyer asked a federal judge in San Diego to either dismiss the charge of lying to authorities or order prosecutors to hand over any evidence that shows McCain knew about his brother's intention to support terrorism in Syria.
Attorneys are expected to argue the motion next week.
Davis writes for the San Diego Union-Tribune.