Challenging a seated judge is not the easiest way to the bench.
Just ask those who ran against — and lost to — Pasco County Judge Debra Roberts in 2004 and 2010.
But Roberts, who has been on the bench since 2002 and is up for re-election this year, again faces challengers in the Aug. 30 primary.
Opponents Scott Tremblay, a private lawyer, and Michael Wilson, a Pasco County Sheriff's Office detective and Army reservist, said the decision to run for judge was about personal timing, not targeting Roberts.
"For me, there's not a whole lot of judicial positions open," Tremblay said.
He and Wilson are both emphasizing their experience to try to convince voters in the nonpartisan race that they're right for the job. If none of the three candidates earn more than 50 percent of the votes, the two top vote-getters will face each other in a November runoff election.
After graduating from Stetson University College of Law, Wilson and his sister opened a private law practice in Pasco in 2004. The practice folded in 2009, though, and Wilson joined the Army Reserve as an officer in the Judge Advocate General's Corps, where he serves as an attorney representing soldiers who are victims of sexual assault.
He also has been with the Sheriff's Office for more than three years, first as a patrol deputy and now as a detective in the professional standards division — a job, he said, he excels in because of his legal experience.
"I have a unique background," said Wilson, 38, of Hudson. "I think when you have a candidate who has advocated for someone in court, has worked for the state and federal government, and has handcuffed people and taken them to jail, I think that's invaluable experience."
When his law firm closed, Wilson, who enjoys fishing, hunting and umpiring youth baseball games, was forced to declare bankruptcy in 2011. Still, nearly five years later, weighted by student debt, he lists his net worth as negative $48,144.38.
When asked if it would be concerning to have a judge who previously declared bankruptcy, Roberts said it could be.
"You're not able to handle your own business and now you want to be in charge of somebody else's business," she said.
Wilson, though, said the bankruptcy wasn't a result of frivolous, irresponsible spending, just life circumstances. It wouldn't impact his ability to rule on cases, he said.
"I would ask the voter to show trust and confidence in me as a judicial candidate, just as senior leadership in both the military and law enforcement has trusted me with the most sensitive duties within those organizations," he said.
Tremblay, 39, also touts his experience as an asset. He graduated from Western Michigan University's Cooley Law School and worked at the Pinellas-Pasco State Attorney's Office for four years. Then he opened his own practice in 2007 and maintains an office in downtown New Port Richey.
The most rewarding thing about being an attorney, he said, is helping people.
"At the end of the day, I'm a pretty compassionate person when it comes to people, and I've never been able to help people more than I have with a law degree," he said.
One of the highlights of Tremblay's career as a prosecutor was being second chair in the cases against Oscar Ray Bolin, who was convicted of brutally murdering three women in the Tampa Bay area in 1986. Bolin was put to death by lethal injection this year.
As a private attorney, Tremblay has practiced in Hillsborough, Pinellas, Pasco and Hernando counties, doing defense, family law, wills and trusts, estate planning and some personal injury cases, he said. The exposure to different court systems, he said, gives him perspective to fix some of the problems he thinks ail Pasco County Court.
"I think that we need to have a more efficient judiciary, and I have a skill set for that and tools to be able to do that from my exposure in other jurisdictions where I've practiced," said Tremblay, who volunteers with the Rotary Club and in Pasco County Teen Court.
Tremblay, of Land O'Lakes, has raised more money for his campaign than Wilson and Roberts, though $7,000 has come from the same source. Six businesses that list local businessman Nicholas Borgesano as their registered agent each donated $1,000 to Tremblay. Borgesano, whom Tremblay represented in a recent ordinance violation case, also personally donated $1,000. Separately, last November, Borgesano was also arrested for grand theft in connection to a $200,000 brick paver heist in Hernando County. The charges against Borgesano were ultimately dropped, court records show, though his father pleaded no contest.
When asked about the contributions, Tremblay said he saw no issue with them.
Before Roberts, 63, of Trinity, became the county's first African-American judge, even before she was a lawyer, she was a social worker.
"And one thing I noticed was that the laws that applied to folks who wanted help didn't make a lot of sense to me," she said. "Somebody suggested that the folks who are making the laws are lawyers. So I said, 'Okay, that sounds like something I might want to do.' "
She hoped to become a legislator after law school, but an internship at the statehouse turned her off to politics. Instead, she took a job as an attorney with the then-named Bureau of Business Regulation, and later worked as a senior staff attorney in the administrative offices of the Florida Supreme Court. She moved to Pasco County in 1994 to become 6th Circuit court counsel and, preside over small claims and child support cases.
The never-married judge said she would like to remain on the bench because she sees the difference she makes in people.
"I like to see people change," said Roberts, who is on the board of directors of Youth and Family Alternatives. "My favorite part actually is when people come back. I'll put them in jail, and they'll come back and say, 'Judge, I wanted to come back and tell you what I've been doing with my life.' "
Tremblay has hit Roberts for her poor performance on a survey of local attorneys who score judges based on certain criteria. In 2014, the first year of the survey, she had the lowest score of any judge in the 6th Judicial Circuit, which encompasses Pinellas and Pasco counties. In 2015, she came in 65th of 68 judges.
"I'm actually disappointed in this," said Roberts, who hadn't previously seen the survey.
She dismissed the survey as a popularity contest, "because if a judge does everything an attorney wants her to, they just love her," she said. "... I often disagree. I tell them I disagree."
The survey's validity has been called into question. Thomas McGrady, who served as 6th Circuit chief judge before stepping down in 2015, previously told the Times that only a fraction of the attorneys who were asked to participate — just more than 100 of several thousand — actually submitted responses.
Also, Tremblay, who has appeared as an attorney in Roberts' courtroom, alluded to Roberts often overriding plea deals worked out between the prosecution and the defense. Tremblay, for his part, said he never would override a legal deal.
"I can tell you, if I get elected, I will not be a rubber stamp on all deals," Roberts said in response. "That is not me. That is not going to happen."
Contact Josh Solomon at (813) 909-4613 or [email protected] Follow @josh_solomon15.
This article has been revised to reflect the following correction: Scott Tremblay, a candidate for Pasco County judge, previously represented Nicholas Borgesano in an ordinance violation case. A previous version of this article incorrectly stated the type of case.