I understand why City Attorney offices -- that is, the office of the attorney general for civil and minor criminal actions pursued by (and against, in the case of civil actions) a city -- in large cities tend to be run by incompetents.
First, the City Attorney is a political figure who has worked toward his/her position based on contacts, not necessarily ability in the courtroom. In other words, many of these folks and their staffs are simply hacks. This contrasts with most District Attorneys who, although elected by the voters in their county or city, usually spent YEARS trying criminal cases.
Second, the City Attorney has limited budget resources, therefore it cannot attract the "best and the brightest" attorneys because it pays such low rates; and the civil docket the City Attorney runs has far fewer opportunities for trials than the district attorney's office. This explains why top lawyers will intern with, loan out to or start their careers with a DA's office.
Third, the City Attorney is directly responsible to the mayor, city manager, city council or other repository of the city's lawmaking power. In other words, that office must respond to the hacks who run the city. And in our nation's largest cities, that means political gladhanders known more often for their corruption than their managerial skills.
So this explains in part why the Washington DC attorney general's office, essentially the DC City Attorney, completely mismanaged the contract it had with the large and venerable law firm, Venable, LLP, to handle litigation matters relating to the construction of the new baseball stadium that DC is building for the Washington Nationals. Whether Venable acted improperly is open to interpretation. The sophisticated client needs to restrain its attorneys if they begin to act outside the scope of their engagement but the attorney owes the client a fiduciary duty and the duty of utmost loyalty. The mismanagement of taxpayer funds by the city, however, seems clear.