Bob Dees was just 6 years old when his father died in a car accident.
He was too young to have many memories from that time. But his mother remembers her son asking a question well beyond his years: “Are we going to be OK with money?”
The baby of the family was insightful enough to realize his mom’s elementary school teacher paycheck was the only source of income for the now family of three.
Dees didn’t want to be a burden or cause trouble for his mother. Neither did his sister, who is two years older than him.
“So I was always sort of a goody two-shoes kid,” he said.
Though he grew up without a father, Dees found a strong male influence in one of his uncles from his mother’s side of the family. The uncle was a well-respected lawyer in the family’s hometown of Lakeland.
“I wanted to emulate that,” Dees said.
And he did, graduating from the University of Florida Levin College of Law in 1987.
Dees has worked for respected small firms and the imposing Holland & Knight.
His career has included First Amendment, maritime and insurance defense cases.
And he’s won major victories in a years-long battle against the Police and Fire Pension Fund.
Dees had thought about being a judge for a long time. But not before the pension fund issue was settled.
“That was not a case I could walk away from,” said the shareholder at Milam Howard Nicandri Dees & Gillam. “I had to do it.”
After his one-two punch of victories against the pension fund in 2015, Dees began to pursue a job on the bench.
He made the finalists’ list his first time out, but the open spots went to John Guy and Steve Whittington in December.
After that he was passed over for an opening on the 1st District Court of Appeal.
But then came the right call from the wrong area code last month.
At age 53, Dees was appointed to replace Harvey Jay as a Circuit Court judge.
A guiding hand
Dees’ uncle, Dennis Johnson, helped guide his nephew at key moments throughout his life.
Like the time a girlfriend wanted Dees to go to a local community college. “He told me that wasn’t happening,” Dees recalled of his uncle.
Instead, the two compiled a list of colleges, including Washington and Lee University, where Dees attended.
When it came time to pick a major, his uncle stepped in again, encouraging Dees to study something he could use in the business world versus pursuing a liberal arts-related degree.
He majored in business administration and accounting but also took a lot of liberal arts courses.
“In the end, I think I probably remember more from the liberal arts classes than I do from accounting,” Dees said.
He recalled a friend who majored in history used to joke he was going to open up a history repair shop.
Dees decided in college to become a lawyer, believing he would enjoy the job’s intellectual challenges.
He also wanted to be “part of a system that holds society together.”
The career choice wasn’t something his uncle overtly influenced at all.
Dees didn’t go into the same practice areas as his uncle, who handled estates, trusts and transactional work. Johnson didn’t do trial work. “It makes you old before your time,” he told his nephew.
Dees points out the irony in that Johnson gave him the advice when his uncle was in his 40s and bald or going bald.
Johnson helped steer his nephew to his first clerkship in Jacksonville in the summer of 1986, when he set up interviews for Dees with Jake Schickel and Howard Coker.
One of the more memorable parts of the interview came when Schickel told Dees the firm was primarily a defense firm.
Shortly afterward, Coker said to Dees, “You understand we’re primarily a plaintiff’s firm?”
Dees nodded yes both times.
As the first clerk to arrive that summer, Dees remembers sitting in the library with his first batch of research memos.
And, in the days long before the internet, he remembers staring at the shelves lined with research books.
“I’m sure the answers are in these books somewhere,” he told himself. “So I’ve just got to figure out how to find the answer.”
He figured out pretty quickly.
Dees did enjoy watching the second clerk on his first day, as he sat down with his research memos.
“I remember sitting there thinking, ‘You don’t know how to do this either, do you?’” he said, with a laugh.
Building a career
After law school, Dees joined the firm of Wahl & Gabel in 1987. It merged with Holland & Knight in 1998, where Dees stayed until 2002.
He wanted to return to a small firm and became a shareholder at Milam Howard.
Dees credits his partners for their support and patience as he worked through the pension fund cases. He signed on in August 2010 to represent Curtis Lee in a years-long legal fight over public records fees.
The following year, Dees represented Lee and the Concerned Taxpayers of Duval in a case to get the 30-year agreement reached in 2000 between the city and the fund thrown out because the negotiations violated the state’s open meetings laws.
In March 2015, Circuit Judge Thomas Beverly declared the 30-year agreement void ab initio, meaning it has been invalid from the start.
The next month, the Florida Supreme Court determined Curtis was entitled to about $83,000 in legal fees and interest.
The court agreed with Dees’ contention that the law doesn’t have a good faith exception, which would allow public agencies to avoid paying legal fees if they didn’t intentionally violate the law.
The case was the only time Dees got to argue before the state Supreme Court. It fit into that intellectual challenge he was looking for.
It also was the perfect timing to start considering his next job.
Road to the bench
When Dees applied in the fall, he was one of 32 seeking one of the two open spots in the 4th Circuit and among the 22 candidates to be interviewed.
Dees admits he was nervous going into the interview, but it turns out those nerves didn’t hurt him. He got a call that night from Chip Bachara from the local Judicial Nominating Commission, asking what he thought about the interview process.
“I said I let like I was at an oral argument and the issue was me,” Dees told him.
“Well,” Bachara told him, “you won your argument.”
That meant Dees would be one of 12 names sent to Tallahassee.
After that, it was a waiting game to see if he got a call from an 850 area code, meaning it was the governor’s staff and he didn’t get the job, or from a Naples area code, which is the area code of the governor’s cellphone.
As he was getting ready to go to the firm’s Christmas lunch last year, his cellphone rang. It was an 850 number.
“Dang it,” he said, or maybe something a little worse.
He emailed his partners right away, so they would know before he arrived at the lunch that he didn’t get the appointment.
When he applied for a spot on the 1st District Court of Appeal in February, he didn’t think he would get it, but went through the process. His name was not among the finalists sent to the governor.
When another 4th Circuit spot came open, he applied and made it to the second round again. Then he waited for the call to his cellphone.
It came June 24 while he was trying to schedule something personal. He looked down and saw an 850 number.
“Dang it,” he said, or maybe something a little worse again.
“Hello, this is Bob Dees,” he said, “intentionally channeling all of my disappointment through the phone” to who he expected to be someone from the governor’s staff.
But it wasn’t.
It was Scott calling to congratulate him on his appointment.
Dees said thank you, then asked for a second because of the emotional boomerang he’d just gone through.
“You called me on an 850 number and we all know that if you get called from 850, that’s your staff and you don’t get the position,” Dees said to Scott
The governor kind of laughed and said, “Yeah, I guess that’s right.”
Dees said his wife of 21 years, Margaret, was really happy for him.
“She knew that I wanted it badly and she saw how disappointed I was the first time when I didn’t get it,” he said.
Margaret Dees is an attorney, as well, and a senior vice president at Jacksonville University.
The couple and their daughters, Vivian, 17, and Lilah, 14, didn’t talk much about Dees’ second effort for a circuit judge spot. After all, with six candidates, there was a better chance he wouldn’t get it than he would.
But he did.
Taking the next step
Getting the appointment is bittersweet for Dees. It’s the next step he wanted for his career, but he’ll be the leaving the firm after 14 years.
“They’re like family,” Dees said.
He learned from them, they learned from him. And they really supported him in his pursuit to be a judge.
Dees will wrap up his work at Milam Howard at the end of the month, go on a college trip with one of his daughters and begin his new job Aug. 8. He’ll start in the civil division but could be shifted anywhere in the circuit in January.
He’s the new guy, he said.
Something he hasn’t been for a long time. But something he’s wanted for a while.
@editormarilyn
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