Flirting bank robber told woman he’s a ‘sugar daddy,’ leading to charges after dramatic Loop shootout in March that left guard wounded, feds say

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Weeks after a man shot a security guard during a Loop bank robbery, officials tracked him down and say his flirting led to charges, federal authorities said Wednesday.

The criminal complaint, made public Wednesday, reveals new details of the March 9 bank robbery and shootout and shows the suspect, Jawad H. Hakeem, was identified by authorities in part because he stopped to flirt with a woman in an alleyway before holding up the Fifth Third Bank at 1 South Wacker Drive.

Hakeem was charged in the complaint with bank robbery. He is currently in the custody of the Lake County sheriff’s department after being arrested in Waukegan.

Hakeem pointed a gun at two bank employees as he walked in at 2:59 p.m.

“I’m robbing you! Get down! There is a bullet in the chamber, ” he yelled before tossing a plastic bag at the employees, according to the complaint.

The man looked at the employees’ badges. He wanted $100,000 in $100 bills and wanted them to hurry, he told them as he said their names. He would kill them if they didn’t, he added, according to the complaint.

Meanwhile, a third employee in a breakroom saw the robbery unfolding in the lobby through a live video feed and called 911 and pressed a panic button, the complaint said.

At the same time, a security guard who was standing outside the bank with his back to the window turned and saw Hakeem, the complaint said. The alleged robber was still pointing his gun. He seemed to see the guard just as the guard saw him, according to the charges.

The FBI released this image of a gunman from a bank robbery in the first block of South Wacker Drive at about 3 p.m. on March 9, 2023. A 59-year-old security guard was shot during the heist, the FBI said.

The plastic bags had been filled with around $23,900. Hakeem grabbed the bags and rushed to the bank’s exit, according to the complaint.

The security guard drew his gun, a .38 caliber revolver loaded with seven rounds. The robber pointed his gun at the guard as he approached the revolving door and the two men began firing at each other, the complaint said.

The security guard took cover to reload. He had been shot in the hand by one of the nine 9-millimeter bullets the robber had apparently fired. The 59-year-old suffered a graze wound and declined to be taken to a hospital, police said at the time.

The robber lost his balance and dropped some of the money, then briefly knelt to scoop the cash from the ground and stuff it into his plastic bags. Then, just two minutes after the robbery began, the man fled, according to the complaint.

But as dramatic videos of the shootout spread, he couldn’t get far enough away. His penchant for smooth-talking women proved vital to the charges he will now face, the complaint shows.

A woman who came forward as the robber’s image circulated had seen the man — black coat, red knit cap, blue jeans and black and blue ski gloves — in a nearby alleyway just 15 minutes before the robbery, she said.

She had been smoking a cigarette when he approached her and struck up a conversation, the woman said. He asked her for a smoke and told her that he was a “sugar daddy,” adding that he was going to run for president in 2024, according to the complaint.

The woman couldn’t see the man’s face, but he gave her his phone number, even telling her a mnemonic device so she could easily recall it, according to the charges.

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After the woman shared the easy-to-remember number with police, the shared digits led authorities right to Hakeem, the complaint said. A database search showed the number belonged to him and led authorities to his Facebook page.

There, Hakeem made the same boast he made to the woman that helped turn him in: “Jawad HaShem Hakeem will be the next President of the United States of America,” he said in a post in which he also shared his address, email, phone numbers, birthday and shoe size, according to the charges.

The information matched contact information on a Chicago Police Department report related to a theft from the week before and a Waukegan Police Department report related to a Feb. 13 arrest.

He repeated his “sugar daddy” advertisement in another post. In the photos Hakeem shared of himself, he appeared to match the height, weight and skin tone of the robber.

Information Hakeem shared with Waukegan police after he was arrested March 13 on an active warrant and theft charges showed he had rented Room 254 at a Best Motel in the Woodlawn neighborhood on Chicago’s South Side shortly after the bank robbery, according to the charges.

The investigators tracking him down in relation to the bank robbery visited the motel. He didn’t check out the day he was arrested, they learned. But when hotel staff had walked in that same day, they found his clothes and a gun, the charges said.

The clothes, including a pair of black and blue striped ski gloves, matched the outfit worn by the bank robber. The gun was consistent with the nine shell casings left at the scene, according to the complaint.

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