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“I am aware of a number of issues and questions being raised about this security firm and, in particular, this contract,” said council member David A. Catania, at-large independent, in an email from his chief of staff. “But [Mr. Gray] committed to send the contract renewal to the council for review, and I have no reason to believe they wont honor that commitment.”

The school security contract has a controversial history. In October 2009, the city’s previous contractor, Hawk One, collapsed after compiling a shoddy performance record, according to the Aug. 17, 2010, letter Mr. Gray signed along with his former council colleagues.

“It’s in everyone’s best interest to avoid a repeat of the poor performance and irresponsibility we experienced with Hawk One … by saying no to its replacement, U.S. Security Associates,” the letter states, after referring to USSA’s record of fines and litigation in more than a dozen states.

A statement Monday from USSA officials blamed the employees union for spearheading a negative media campaign because of collective bargaining disagreements with the security firm.

“The SEIU is taking every opportunity to spread negative publicity about the company,” the statement read.

The company also noted that despite being one of the largest security guard companies in the U.S., it has a relatively low rate of litigation. The firm, in the statement, also said that any failed security penetration tests were for training purposes only.

The USSA contract marked the return of Watkins Security Services, a local partner that has its own troubled history having been dumped by the District in 2005 - but it does have a favorable relationship with Mr. Gray. D.C. records show that USSA and Watkins have been fined more than 70 times by the Department of Real Estate Services for security and contract violations citywide in the past year or so. And the employees union claims Watkins has a record in D.C. of minimum-wage violations.

A July 2005 audit by the D.C. Office of Inspector General also found persistent problems with the firm’s employee screening and training procedures, and a 2004 audit concluded that the District overspent by more than $8 million in awarding a $42 million contract to Watkins instead of more-qualified bidders.

Mr. Hamilton, who has more than 400 employees, said of his company’s past: “Like any company, there have been challenges, but we have met them.”

The retired detective declined to answer specific questions about the contract, which grants his company 35 percent of the profits. “It’s not really our contract,” Mr. Hamilton said. “We’re fortunate to get a piece of it, and we’re trying our level best to perform to standards.”

Of his relationship with the mayor, Mr. Hamilton said the two have known each other for more than 25 years. “We are acquaintances, and we have worked together in the past,” he said. “I know he respects me, and I greatly respect him.”