The target of an elaborate, lengthy and ultimately failed “Mr. Big” sting has filed a $19-million lawsuit against a dozen officers from three Ontario police forces who ran a controversial police operation aimed at solving Durham region’s oldest unsolved murder.

In a rare move, Alan Smith is also suing the Attorney General of Ontario and three Crown attorneys who counselled homicide investigators throughout their increasingly complex undercover operation. Smith alleges the Crowns knew, or should have known, the police tactics in the case created a risk of false confessions or wrongful imprisonment.

“The police misused their power and breached their oath of office. The Attorney and his agents misused and abused their offices,” Smith alleges in the statement of claim, filed in Toronto court Friday.

The conduct of all involved in the Mr. Big sting was “outrageous, reckless, wanton, entirely without care, intentional, deliberate, callous, (and) disgraceful,” alleges the claim, prepared by lawyers Richard Posner, Brian Eberdt and Alison Craig.

In addition to Durham police, the statement of claim also names the Ontario Provincial Police — where two undercover officers are employed — and police services board for York Regional Police, where one other undercover officer is employed.

The police forces named in Smith’s claim either did not respond to the Star’s requests for comment Friday, or declined to comment because of the ongoing lawsuit. Statements of defence have not yet been filed.

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Mr. Big casts a long shadow in prisons, despite Supreme Court ruling

Judy Phillips, a spokesperson for the Ministry of the Attorney General, said “the claim is being defended” and that provincial legislation does not permit the Crown attorneys to be individually named in the lawsuit.

“The crowns should not have been named personally,” she said in an email.

In July 2014 Smith was acquitted of first-degree murder in the 1974 slaying of 22-year-old Beverly Smith (no relation). During a Mr. Big police sting, Smith had confessed — twice — to being involved in the shooting death of the young mother while she was alone in her Raglan home, her infant daughter in the next room.

Smith was in jail awaiting trial for more than four years.

Ontario Superior Court Justice Bruce Glass quashed the case and threw out all evidence gathered during the nearly yearlong sting after finding the police operation “pushed the envelope” and produced confessions full of holes “you could drive a Mack truck through.”

“In my opinion, the use of this information obtained in this manner would shock the sense of trial fairness to Canadian society,” Glass wrote.

Three days after Smith’s acquittal, the Supreme Court of Canada placed strict new limits on the Mr. Big technique, ruling that any confessions produced during the gambit must be carefully scrutinized before being ruled admissible in court because of the danger of false confessions.

Created in Canada in the 1990s, the Mr. Big sting is an undercover operation aimed at obtaining a confession from a suspect, often someone police believe is responsible for a crime but have little evidence against. Often used in cold cases, the subterfuge involves convincing the target of the sting that he is consorting with criminals and must confess to a serious crime — usually to the boss, Mr. Big — to gain trust and entry into the criminal group.

Critics have said the sting is unethical and produces unreliable confessions. It often offers the target companionship and significant financial benefits, making the sting particularly effective on socially isolated and poor suspects.

Among the biggest criticisms is that police contrive a situation that is so beneficial to the suspect — they suddenly have new friends and money — that they have more incentive to lie than tell the truth when prodded about a murder; in essence, they will say anything when membership in the group is on the line.

The Supreme Court, however, did not entirely ban the sting, acknowledging that it can produce “valuable evidence.” A confession, for instance, can be more reliable if it includes information only the killer would know.

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The sting involving Smith was launched after he had already been charged, then cleared, in Beverly’s murder.

Smith first became a prime suspect in 2008, when his ex-wife came forward with new information that implicated him. But the case quickly fell apart when her evidence was proven false. Still convinced Smith was guilty, Durham police regrouped and launched their Mr. Big operation, coined “Project Fearless,” in 2009.

Investigators lured Smith in with his pastime, fishing, by tricking him into thinking Smith had won a weekend fishing package. An undercover officer — who cannot be identified because of a publication ban — posed as another lucky contest winner and easily became fast friends with Smith, who was a broke loner living in his daughter’s basement.

Gradually, the undercover officer began involving Smith in fake drug deals and paying him for help. Soon Smith was introduced to his new best friend’s supposed crime boss, the so-called Mr. Big, then pushed into increasingly bizarre situations meant to provoke a confession.

At the height of the sting, Smith was made to believe he had become involved in a murderous robbery gone wrong. Using sheep’s blood and a weighted-down mannequin wrapped in tarps, investigators tricked Smith into believing he’d helped dispose of the body of a man killed by Mr. Big.

Because Smith now had supposedly incriminating information about Mr. Big, the undercover officer posing as the crime boss told Smith he must provide information about his own criminal past, as insurance that Smith wouldn’t go to police. Smith went on to make two wildly differing confessions, one in which he killed Beverly Smith alongside another man, and another where he did it alone.

“They put me through all kinds of horrific scare tactics. I thought my life was in jeopardy,” Smith, now 63, told the Star in 2014. “Is this what we do in this country?”

Smith’s lawsuit alleges police exploited Smith’s psychological weaknesses “to cause severe and lasting emotional harm and psychological damage.”

“If not for the defendants’ negligent and unlawful actions, (Smith) would not have been subjected to the anxiety and trauma of the Mr. Big operation; would not have been arrested as a result of his false confessions; would not have been prosecuted for first degree murder; and would not have spent any of this time in prison,” the statement of claim alleges.

After Smith’s acquittal, Alison Craig, who represented Smith alongside Joanne McLean in his criminal proceedings, told reporters police had “not only crossed the line but they trampled it.”

“It resulted in a false confession and an innocent man being in jail for many years, and hopefully it won’t be repeated.”