Minutes before he robbed a Loop bank and exchanged gunfire with a guard earlier this month, the FBI says Jawad Hakeem met a woman smoking a cigarette in an alley and struck up a conversation.

He was a “sugar daddy,” he told her, and was running for president in 2024, according to a federal complaint. He gave her his phone number, saying it was a “special” one given him by T-Mobile. But Hakeem was not done leaving a trail for federal agents, according to the complaint: He left behind the gun and the gloves from the robbery when he skipped on his bill at a motel in Woodlawn.

On Tuesday, Hakeem was charged with bank robbery as he sat in a jail cell in Waukegan, where he was arrested last week for a theft there.

Hakeem is accused of walking into the Fifth Third Bank at 1 South Wacker around 3 p.m. March 9 and aiming a gun at two employees while yelling, “I’m robbing you! Get down! There is a bullet in the chamber,” according to the federal complaint. 

Hakeem called the workers by name, apparently reading their name tags, and threatened to kill them unless they gave him $100,000 in 100-dollar bills. While the employees filled two plastic bags with cash, a guard standing outside the bank turned and spotted Hakeem holding the gun, the FBI said. 

Hakeem grabbed the bags containing nearly $24,000 and rushed to the exit. He and the guard fired at each other near the bank’s glass revolving doors, and the guard was wounded in the hand, the FBI said. Hakeem appeared to lose his balance and dropped some of the money.

Surveillance video shows Hakeem kneeling to gather up and stuff money from the ground as the guard retreated to reload his gun, the FBI said. Nine casings from Hakeem’s gun were recovered.

About 15 minutes before the robbery, the FBI said Hakeem walked up to the woman smoking a cigarette on Arcade Place, not far from the bank. Later that day, the woman saw news coverage of the bank robbery and noticed he was wearing the same clothes as Hakeem, the FBI said.

Federal agents tracked Hakeem through the phone number and Facebook postings. In one post, two days after the robbery, Hakeem called himself “Prince Hashem” and wrote, “I’ve been a Sugar_Daddy since 2005.” Another post from the same date says, “Jawad HaShem Hakeem will be the next President of the United States of America.” 

The FBI said it learned that Hakeem had been arrested in Waukegan on March 13 for a theft and had listed a motel room in Chicago as his address. Staff there said Hakeem had failed to check out and his belonging were cleared out of the room, including a handgun, which they turned over to police.

The gun appeared to be the one used in the robbery, the FBI said, and had been stolen from a car in Naperville on March 2, a week before the bank was hit. Among the clothes left behind was a pair of black- and blue-striped ski gloves that matched what the bank robber wore, according to the FBI.