Near the end of Bruce Castor’s long round of questioning with Bill Cosby’s defense team at a hearing earlier this month, he told Cosby attorney Brian McMonagle, “I’m not on your team here. I want them to win.”

It’s something he repeated in an interview with Billy Penn: “I’m still on the prosecutor’s side. I still want Cosby to get convicted.” But Castor, the MontCo DA from 2000 to 2008, also admits his longtime friendship with the prosecutor, Kevin Steele, has soured. And while McMonagle may be on the side Castor wants to fail, he reportedly supported Castor in his bid to reclaim the district attorney’s office and was once Castor’s co-worker early in their careers.

Montgomery County may be the third-largest county in Pennsylvania, but connections between the lawyers, the judge and Cosby are making it seem like a small town. On the periphery of a sexual assault case concerning what happened between Cosby and Andrea Constand, there are former political battles, ruined friendships and even a legal relationship between Castor’s father and Bill Cosby.

“People who gravitate to courtroom law end up being a relatively small group,” Castor said. “And since I was the DA, a generation, if not two generations, of lawyers went through the office while I was there. So it would not be unusual that we all know each other.”

Castor started at the Montgomery County district attorney’s office in the mid-1980s, rose through the ranks and ran for district attorney in 1999. To be in the best position to win, he needed the endorsement of the county’s Republican Party in the primary. The Republican opposing him was Steven O’Neill. O’Neill is now the judge in the Cosby case. So when Castor was on the stand earlier this month, two past political opponents — the judge, O’Neill, and the prosecutor, Steele — were participating in the case.

Castor got the endorsement in 1999, went on to win the election in the fall and then won again as an incumbent in 2003, setting him up to be the DA considering Constand’s accusations.

Family ties

Castor’s father was surprisingly connected to Cosby in a way Castor said he didn’t know as he oversaw the case. In June 1983, Cosby bought the Elkins Park mansion at which Andrea Constand would later accuse him of sexual assault. He purchased it for $225,000 in a deal arranged by Bruce Castor’s father, also named Bruce Castor. Castor Senior and F. Eugene Dixon, who bought the house a few years earlier, are listed as the sellers on the deed.

Dolores Troiani, Constand’s lawyer, told Billy Penn she was not told of the sale by the former Montgomery County District Attorney. In a Daily News article about the home, published in 2005 shortly after Castor announced he would not press charges, late Cosby attorney Walter Phillips Jr. said Castor had disclosed the sale to him. Troiani also told the Daily News back then she hadn’t been made aware of the details. She told Billy Penn she did not want to comment any further about the matter. 

Castor said he did not recall disclosing the information to either side because at the time he wasn’t aware his father had even presided over the transaction.

“How could I disclose something I did not know?” he said. “I think a reporter found it.”

Castor recalls his father later explaining his work with the Cosby sale as an odd coincidence. Castor’s father worked at the same firm as the lawyer originally handling the sale. That lawyer was sick the day of the sale, and Castor’s father filled in. Castor said his father could barely recall the sale because Cosby wasn’t present.

“How something my father did when I was in law school could affect any decision I would have,” Castor says, “is complete nonsense.”

But attorneys who have followed the Cosby case said if Castor knew about the transaction he needed to tell both legal teams — and perhaps should have recused himself.

“That absolutely is relevant,” said Jeffrey Lindy, a Philadelphia defense attorney and former assistant county solicitor in Montgomery County. “The situation here is that officials need to recuse themselves when there is an appearance of impropriety. The issue is not whether there is actual impropriety or not. It’s the issue of appearance. And Castor should have let the complainant and the complainant’s lawyers know about that.”

Wes Oliver, a Duquesne law professor who attended the Cosby hearing, said that if Constand’s lawyers had been told by Castor and opposed his overseeing the case, their options to remove him from the investigation likely would have been limited.  

“All too often the foxes guard the hen house,” Oliver said. “This sounds like one of those situations.”

Castor could be called as a defense witness if the case ever goes to trial. He could once again be questioned by his former co-worker McMonagle or by Steele, who had an assistant district attorney question Castor at the hearing. Steele and Castor worked together from 1995 to 2008 and then ran against each other for district attorney last year.

“Kevin Steele and I were friends for 25 years before he ran against me and ran what I thought was not an above-board campaign,” Castor said. “So I’d say that friendship’s at an end.”

But, Castor added, he didn’t think their relationship — or any of the ties between the judge, the lawyers and Cosby — precluded them from acting professionally at the Cosby hearing or during his handling of the case.

“At some point,” Castor said, “you have to trust somebody, and that’s how a system generally works.”

Mark Dent is a reporter/curator at BillyPenn. He previously worked for the Pittsburgh Post-Gazette, where he covered the Jerry Sandusky scandal, Penn State football and the Penn State administration. His...