When Bill Cosby hired Monique Pressley last summer, he didn’t merely sign another Washington lawyer to his burgeoning legal team.
He landed a spokeswoman, a relative newcomer to television who quickly flooded the airwaves as the embattled comedian’s chief defender. And, in the bargain, he got a preacher and blogger admired in the black talk-radio and TV world.
Pressley, a product of Howard University’s law school, is no ordinary celebrity mouthpiece. In 2013 she created the Monique Pressley Ministries, “a world-wide evangelical ministry,” according to her website. She’s an entrepreneur who developed “a three-month health and wellness program for women,” as her bio states, with “biblical teachings related to good health and diet” to “provide another alternative for establishing and maintaining financial stability in uncertain economic times.”
Why so many career paths? Pressley declined to comment for this story.
There’s no doubt that she has demonstrated a doggedness as she defends Cosby, the first high-profile client for the solo practitioner. California attorney Gloria Allred, who represents more than 20 of Cosby’s accusers, recently challenged Pressley to a debate on MSNBC.
Pressley, 45, is a renowned debate coach, too.
She later responded smilingly to Allred’s suggestion: “We’re not in high school. We don’t debate. We’re not politicians running for office,” she said on television, adding: “No, we are attorneys with clients.”[After sexual assault charges, Bill Cosby faces jail time — and his legal battles are just beginning.]
Cosby lets her — and pretty much only her — do the talking for him. Says commentator and old Texas acquaintance Roland Martin: “She is the point guard of the legal team.”
“We had her on providing the legal analysis for the case,” says Martin, who had been looking for “really strong female attorneys” for his television show. “She gave great analysis, not just on legal issues. Some folks close to Cosby heard the segment, how she broke down the case and analyzed the case. They reached out to me asking how to get into contact, then reached out to her, and made her a part of the legal team.”
Most of that team is composed of white men. For years, the comedian was represented by Los Angeles attorney Martin D. Singer, a tenacious and sometimes brash advocate for many Hollywood stars mired in scandal. Singer’s 2014 characterization of some accusers’ claims as “unsubstantiated, fantastical stories about things they say occurred 30, 40 or even 50 years ago have escalated far past the point of absurdity” is folded into several defamation suits women have brought against him.
Pressley is scheduled to be at Cosby’s side, as she was for his arraignment, at a hearing Tuesday in suburban Philadelphia. The hearing will be limited to arguments as to whether the former Montgomery County district attorney violated a 2005 oral non-prosecution agreement when the comedian was charged with sexual assault in December.
Veteran Philadelphia criminal defense attorney Brian McMonagle, who has represented rap artists, politicians and a cardinal (in the wake of the priest abuse scandal), is expected to be lead counsel in the Pennsylvania case, based on allegations that Cosby drugged and assaulted a former Temple University employee in 2004 at his suburban estate.
Although McMonagle has a history of being cozy with the press, he has remained largely silent since the arraignment.
In the fall, as the entertainer’s legal woes swelled and honorary degrees were revoked, the Cosby team parted with Singer. Instead of performance halls and television specials, Cosby may well spend his twilight years in courtrooms and legal offices at the center of multiple lawsuits and countersuits from California to Massachusetts.
Pressley is the same age as or younger than many of the comedian’s accusers. She is described on her Twitter bio as “Motivator, Legal Analyst, Radio Host — Breathe Through It, Attorney, Teacher, Preacher.”
“I thought she handled herself very well, being a low-key black woman,” says veteran defense lawyer Victoria Toensing, of Pressley’s early television appearances “In the politics of the law, that is a very smart move. You want a woman.”
“She’s doing as well as she can under the circumstances,” says Howard Bragman, a longtime crisis-PR strategist in Los Angeles of Pressley’s television support of her client. “But I don’t think it’s going to change the game and the perceptions of Bill Cosby. He’s in too deep.” He characterizes Cosby’s predicament as “one of the biggest falls from grace in the history of entertainment.”
Frequent television appearances aren’t always the solution to improving image or changing the conversation, Bragman counsels. “Sometimes I just like to shut up; just because you can talk, doesn’t mean you should talk.”
Pressley was employed for three years at the District’s Public Defender Service before, as her bio states, working as a contract attorney at a firm in Maryland.
She worked two stints in the city’s attorney general’s office. Her most publicized assignment, associates recall, was the 2002 Pershing Park arrests class-action settlement after almost 400 protesters and bystanders were arrested during demonstrations against the World Bank.
In 2008, she started the Pressley Firm, a one-woman shop on K Street that, according to its website, specializes in “complex civil litigation, new business incorporation and development, and church law issues.”
Her husband, Carlton Pressley, also an ordained minister, runs the Pressley Group, whose services include, its website says, “motivational speaking, consulting services, inter-faith development, government services, real estate acquisition, financial consulting.” He served 15 months as Mayor Anthony Williams’s adviser of religious affairs before being dismissed in 2003 for soliciting a donation from D.C. Marathon organizers, in violation of an executive order. The couple lives in Waldorf, Md., with their three children.
Monique Daniel was raised Roman Catholic in Galveston, Tex. Her godfather was a priest. She graduated from St. Mary’s University in San Antonio, a Marianist institution. A cheerleader and debutante, she showed a strong interest in musical theater and was invited to join Up With People, the motivational music troupe, according to a local news item.
“She was a very formidable debater in school,” says Torey Wilson, a member of her debate class at Ball High School. “I wouldn’t have wanted to ever debate against her.”
Pressley’s most-publicized achievement, before landing Cosby as a client, was as an adjunct professor and coach of the Howard Law debate team that won the American Bar Association’s mock trial competition, triumphing over 18 other schools, including reigning champion Harvard.
“Practice could last anytime from four hours to 10 hours,” says team member L. Chris Stewart. “We would start at 5 p.m. and sometimes not leave the law school until 2 a.m. She’s very, very focused. We had to memorize everything.”
Identical twins Derrick and Errick Simmons, attorneys and politicians in Mississippi, were also members of the team. Team captain Errick Simmons recalled, “She told us, ‘Everything that you do is preparation.’ That has been the model that has guided her life.”
Landing Cosby as a client is “huge,” Derrick Simmons says. “This is what all lawyers live for.”
Bragman, the publicist, has a more nuanced view. “She’s a member of the team, and the face person,” he says. “She’s been dealt a bad hand. But it’s not hurting her. It’s helping her brand.”
Alice Crites contributed to this report.