Another settlement that might have been much higher was paid in May 2005 to Maureen Ward, who, in 2001, was driving northbound on the expressway. At the same time, BPD officer Emmanuel Dambreville and his partner were chasing a suspect through the streets of Boston, defying three orders to stop the pursuit. The pair ultimately followed the suspect car the wrong way up a ramp and on to the north-bound expressway, violating department policy. The driver they were pursuing slammed head-on into Ward’s car. Ward was injured and her car was demolished; four years later, in May 2005, the city settled with Ward for the maximum she could receive: $100,000.

This settlement limit presumably deters a lot of nonsense litigation, but it also keeps real victims from bringing lawsuits. With no hope of a large award, attorneys rarely take these cases on contingency, and few victims have the means to spend tens of thousands of dollars up-front.

This $100,000 cap does not apply, however, to civil-rights violations, including employee discrimination and wrongful imprisonment, or privacy violations such as unconstitutional strip-searches. Those types of cases cost the city dearly — and the price has only risen over the past 15 months. So far there have been two wrongful-conviction settlements (with Miller and Cowans). Plus, a jury has awarded former BPD Sergeant William Broderick $1.5 million, excluding attorney fees, for his claim that he was fired after he blew the whistle on police abuse of court overtime.

There are more non-damages-capped lawsuits pending — many involving the BPD. Two black police officers, for instance, have sued over a race-discrimination claim. The family of a woman whom police fatally shot in the back of a car has sued. So has a man who was arrested and paraded in front of television cameras for a crime he had nothing to do with. And hundreds of police officers are awaiting final litigation for improper calculation of overtime pay, for which they have already won hundreds of thousands of dollars.

Plus, at least two wrongfully convicted men have major lawsuits pending. A January trial date looms for Shawn Drumgold, freed in 2004 after spending 15 years in prison for the murder of Tiffany Moore. Some observers believe that if his suit is successful, Drumgold — who spent twice as long as Stephan Cowans in prison — could set a new record for damages paid by the city of Boston. “The benchmark is that [wrongful convictions] can get $1 million per year in prison, when everything goes right,” says Kenneth Flaxman, a Chicago attorney who specializes in police-misconduct cases.

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Behind Drumgold is Ulysses Rodriguez Charles, who spent almost 20 years behind bars for rape. Charles’s suit is pending while he answers separate charges that could lead to his deportation.

Of course, some of these lawsuits may not succeed. Even so, they are costing the city millions in legal fees. For litigation such as the Broderick and Drumgold lawsuits, the city must hire outside attorneys to complement its own staff. For this, the city is budgeting $4.8 million for the current fiscal year, up from $4 million two years ago — including $1.3 million for contracted legal services.

Reform? Or repeat?
In theory, civil lawsuits can bring pressure for reform, whether in a corporation or a government. Yet many are skeptical that this works — especially with a city government that, unlike a corporation, doesn’t answer to bottom-line-watching shareholders, and in which politics counts as much as fiscal responsibility. “Usually the city isn’t looking at ‘what’s the problem and how do we fix it.’ It’s looking at the political aspect of settling a multimillion-dollar case,” says Flaxman.

Openly acknowledging and fixing problems is rarely Menino’s MO; instead, he often settles cases quietly, and more often than not the payment, along with any wrongdoing, goes unnoticed. Unlike some municipalities where the city council must sign off on large settlements, Boston allows Mayor Menino to authorize deals and cut checks without notifying anyone. The settlement with Ward, for example, was never reported; nor was Ruggerio’s. Nor was last December’s $140,000 settlement for a woman’s unequal pay at Boston Center for Youth and Families.

There’s also the power of the unions — particularly in the police department — which resist strengthening of the internal disciplinary system. This ensures, some argue, that problem officers are not identified, properly trained, or disciplined before being put back in circulation among the public. Perhaps this was the case with Michael Burgio, the officer who allegedly beat Christopher Ruggerio in 1998. Burgio was one of the officers who, three years earlier, allegedly beat fellow officer Michael Cox, whom the defendants mistook for a fleeing suspect. The department fired Burgio for that incident one year after he allegedly beat up Ruggerio.

Few dispute that the BPD greatly improved its oversight in the early 1990s, following the scathing St. Clair Commission report, which blasted the internal-investigations process. But a Boston Globe review last year highlighted a pattern of very light discipline since 2002. “What I think you’re seeing now is slippage,” says civil-litigation attorney Howard Friedman.