But agent Linda Stein apparently didn't know any of it. The allegations hadn't been reported to authorities or had been dropped, prosecutors say.
More than two years later, Lowery went on trial Monday, accused of stealing more than $30,000 from Stein and clubbing her to death to hide the theft.
Lowery's lawyers acknowledged she stole from Stein and at least one previous employer, but they denied she killed Stein. They said she confessed to the slaying only to satisfy police, thinking that would get her out of trouble.
"Natavia had stolen before. She'd been caught before," defense lawyer John Christie told jurors in an opening statement. "She's told people what they wanted to hear, and she was able to go on with her life."
Stein's daughters say red flags should have been raised about Lowery's past before Stein's real estate firm hired her. But experts say there are limits to how much employers can learn about prospective workers, even in an age of electronic trails and background checks.
Lowery had studied business in college and had office assistant experience when she went to work for Stein, who co-managed influential punk rockers the Ramones before brokering apartments for such clients as Madonna and Sting.
But Lowery also had been accused of stealing $3,000 in a previous job at a Virginia church, Manhattan Assistant District Attorney Joan Illuzzi-Orbon said during a recent hearing. The church fired Lowery but didn't press charges, the prosecutor said.
Church representatives didn't respond to phone messages left during the past week.
Separately, Lowery had been arrested on charges of stealing a roommate's identity, though the roommate ultimately declined to go ahead with the prosecution, Illuzzi-Orbon said.
And when police searched Lowery's apartment after Stein's death, they found receipts for thousands of dollars in purchases made on the corporate credit card of another of Lowery's ex-employers and returned for cash, the prosecutor said. The employer declined to comment.
Lowery had worked for Stein for about three months when the 62-year-old broker was beaten to death in her Fifth Avenue apartment on Oct. 30, 2007.
"I came home, and my mom is in a puddle of blood!" one of her daughters, Mandy Stein, 35, frantically told a 911 operator in a call played in court Monday.
In her disputed, videotaped confession, Lowery said she beat her boss with a piece of exercise equipment in a rage over a series of insults from Stein.
But prosecutors say Lowery killed Stein to silence her about the theft.
Mandy Stein and her sister, Samantha Wells, have filed a lawsuit against Stein's real estate firm and the temporary agency through which it hired Lowery, saying they were negligent for not probing more into the assistant's past. The firm declined to comment; the temporary agency didn't respond to phone messages left during the past week.
Employment-law experts say it can be difficult for companies to delve deeply into potential hires' backgrounds.
Laws in New York and some other states bar employers from discriminating against would-be workers because of arrest records, and even convictions in some cases. Some employers don't bother conducting criminal history searches because of the expense of combing all the different jurisdictions in which a person might have been arrested, said Kyle Maldiner, a New York attorney and employee-relations consultant.
Some accusations of workplace misdeeds never make it to a court.
Companies are often reluctant to disclose them to a former worker's potential new bosses out of fear of being sued by the ex-employee, experts say.
"It's very difficult to get the bottom line on someone's character," said Christopher Davis, a managing attorney with The Ottinger Firm, which specializes in employment issues.
Lowery's trial is expected to continue for weeks. Lowery, 28, faces 25 years to life in prison if convicted.