Southern District Judge Shira Scheindlin (See Profile) has never had a problem going against police and prosecutors where she is convinced that constitutional rights are being sacrificed in the name of security.

Whether such rights are being sacrificed is the core dispute before her in Floyd v. City of New York, 08 Civ. 1034, as the New York City Law Department defends stop, question and frisk as an effective crime-fighting tool against civil rights lawyers who claim minorities are being targeted for searches without reasonable suspicion.

Scheindlin framed the issue at the bench trial on April 5 when she stopped a city lawyer from asking if the practice was effective.

"Whether this is good or bad is of no interest," Scheindlin said. "What I mean by that is there are effective police tactics that might be good for reducing crime but that are unconstitutional. The court’s interest is only with the Constitution, not with effectiveness."

Plaintiffs in this politically charged case are seeking an injunction blocking the police from employing what is alleged to be a top-down policy of violating the Fourth Amendment and to appoint a court monitor to oversee reform of department practices, including training and oversight.

Mayor Michael Bloomberg and Police Commissioner Raymond Kelly have aggressively defended the practice as a means of saving lives by keeping guns off the streets, while the City Council and mayoral candidates are debating creating an inspector general for the New York City Police Department.

In an interview with The Wall Street Journal, Kelly criticized what he said was the influence of civil rights lawyers on election-year politics and took a shot at Scheindlin.

"It’s just a small group and they have intimidated these politicians to take this route," he said. "And also, in my view, the judge is very much in their corner and has been all along throughout her career."

It was not the first time Scheindlin’s rulings have angered law enforcement. In addition to a series of decisions in the Floyd case that went against the city, she has made rulings in two other stop-and-frisk cases involving public housing and police patrols of private property in the Bronx.

In 2003, Scheindlin dismissed the case against Osama Awadallah, a man who denied knowing two of the 9/11 hijackers. She called the case "a perjury trap" (NYLJ, April 30, 2002).

Scheindlin had held that the Material Witness Statute, 18 U.S.C. 3144, only allows for the detention of trial witnesses, not witnesses in an investigation, that Awadallah was detained illegally and that the two perjury charges against him were the "fruit of the poisonous tree."

She was reversed by the U.S. Court of Appeals for the Second Circuit (NYLJ, Nov. 10. 2003), but prosecutors were unsuccessful in removing Scheindlin by claiming she had prejudged the most significant issues in the case and become an "advocate" for the defendant.

In 2006, Scheindlin outraged law enforcement agencies and the relatives of an armored truck security guard and two Nyack police officers who were killed in the 1981 Brink’s robbery when she found that Weather Underground getaway driver Judith Clark had her Sixth Amendment right to counsel violated when she was allowed to proceed pro se and refused to attend the bulk of the trial.

Scheindlin held the trial court should have terminated Clark’s pro se status when it became clear no one would be in the courtroom to represent her interests during the prosecution’s case. She was reversed by the Second Circuit, which said Clark had "knowingly and intelligently waived her right to counsel" and had made a "conscious strategic choice" as "part of a de facto political protest" (NYLJ, Jan. 4, 2008).

The appellate court was correct in its reading of court precedents, Scheindlin said in a recent interview, "but I hoped they would take a fresh look."

In 2009, the circuit reversed Scheindlin’s 2008 suppression of cell phone tapes obtained in a terrorism investigation that resulted in a drug bust. Scheindlin, citing her experience in "numerous drug cases," said the government "has shown it has done little, other than wiretap, in its investigation" which she called an "impermissible shortcut" on the requirement that a wiretap be secured only after a showing that other investigative techniques had failed or were likely to fail (NYLJ, Sept. 2, 2009).

The judge was reversed by the circuit when she took the rare step in 2007 of certifying a class made up of defendant law enforcement officials who were continuing to enforce laws against loitering that had long been ruled unconstitutional (NYLJ, June 28, 2010).

Scheindlin criticized the NYPD in 2010 and found New York City in contempt in Casale v. Kelly, 08 Civ. 2173, and Brown v. Kelly, 05 Civ. 5442, the loitering cases, saying "the city’s obstinance and uncooperativeness throughout" the litigation "is offensive to the rule of law," and that tens of thousands of individuals, especially those who are poor or gay, had borne the "human toll" of the city’s actions.

The judge’s pretrial rulings in Floyd and her rulings in other stop-and-frisk cases have left the NYPD skeptical it will prevail in Floyd.

In January, in Ligon v. City of New York, 12 Civ. 2274, Scheindlin issued a preliminary injunction ordering the police to immediately cease trespass arrests outside of buildings in the Bronx whose owners allow police to patrol their property under "Operation Clean Halls"—or the Trespass Affidavit Program (TAP). The plaintiffs, she said, were likely to succeed in showing the police have shown "deliberate indifference toward a widespread practice of unconstitutional trespass stops by the NYPD outside of TAP buildings in the Bronx."

"Some may take for granted the safety provided by doormen who routinely challenge visitors in their apartment buildings," Kelly said. "Through ‘Clean Halls,’ the police have worked to provide a modicum of safety for less prosperous tenants" (NYLJ, Jan. 9, 2013).

Shifting Ground

Scheindlin is in the unusual position of presiding over a case where the ground is shifting.

In Ligon, the police argued that there is not a pattern of unconstitutional stops but also that it had improved training and guidance for officers on stop, question and frisk, an argument they are also making in Floyd.

"They’re saying ‘There’s not a problem, but we’re fixing it,’" said Jonathan Moore of Beldock Levine & Hoffman, one of the lead plaintiffs lawyers in Floyd.

But even as Bloomberg has stepped up his defense of stop-and-frisk, the rate of stops-and-frisks dropped to 525,000 last year from 684,000 the previous year.

The most recent statistics shows an even more dramatic drop, as stops have declined from 203,500 from Jan. 1 to March 31, 2012, to 99,788 during the first three months of 2013. The NYPD says the drop is not a result of a change in policy, but simply reflects what officers are seeing on the street.

But City Council Speaker Christine Quinn, a leading candidate to replace Bloomberg as mayor, claimed recently that her intervention on the issue, and the council’s moves toward appointing an inspector general, have forced the NYPD to reduce the number of street encounters.

All of this means that Scheindlin is dealing with something of a moving target as she weighs liability and, if so, a court-appointed monitor, which, in the eyes of City Hall and One Police Plaza would be even worse than an inspector general.

It also means that lawyers for both sides have to incorporate this changing landscape as they near closing arguments on May 20.

Heidi Grossman, deputy chief of the Law Department’s Special Federal Litigation Division, raised the specter of NYPD oversight, and highlighted the pressure on Scheindlin, during opening argument.

The plaintiffs, Grossman said, want to "divest the NYPD of control over how the NYPD investigates crime."

But, as a counter, the plaintiffs, led by Darius Charney of the Center for Constitutional Rights, Moore of Beldock Levine and Taylor Hoffman of Covington & Burling, argue that court oversight is required because the city failed to live up to its promises in a settlement of a 1999 lawsuit challenging stop, question and frisk polices in Daniels v. City of New York.

In Daniels, the city agreed, among other measures, to maintain an anti-racial profiling policy and document that stop and frisks are being performed based on reasonable suspicion on forms that are regularly audited.

Scheindlin approved the settlement in 2003, but when the number of stops soared and the Center for Constitutional Rights filed suit again in 2008, the case went to her.

Now, 14 years after litigation over the divisive issue began, the ball is still in Scheindlin’s court.