Rockie Pennington, GOP mainstay and adventurer, dies

As he set his course for this year’s explorations, the main problem Roger “Rockie” Pennington faced was how to pack heavy enough for the Nepalese Himalayas: light enough for the Sahara, but festive enough for the nightlife in Kathmandu.

“So, you see my dilemma,” he wrote on his blog in March. “How do you dress for extreme cold, extreme heat, beach, city tours, nightlife, visiting holy places and just generally trying to stay comfortable with just one carry-on?”

In recent decades, Pennington had become increasingly drawn to his quest to meet and greet the world, or at least most of it. It was a long journey from his impoverished childhood in West Virginia, working three jobs to get through college and eventually running Direct Mail Systems (DMS), an industry leader in political direct mail.

Pennington, a scrappy campaigner and an even more loyal friend, died Aug. 27 in Islamabad, Pakistan, of malaria, his family said. He was 71.

The company he led for 25 years praised Pennington’s acumen and execution.

“An adviser to many of Florida’s Republican leaders over five decades, Rockie was a political pioneer, a mentor and friend,” DMS said in a statement. “His presence will always be felt in our facility. DMS is thriving today in large part due to the legacy of leadership he left behind.”

It says something about the scale of his ambitions: the blog, RockieontheRoad.com, came as an afterthought, a glorious denouement. In retrospect, one of the biggest challenges was the ascent of Republican politics in Florida. He was involved at a granular level, part of the College Republicans at Florida State University, where he caught the eye of Jack Latvala, then a field director for the Republican Party of Florida.

“I hired Rockie into his first political job, as a field representative,” Latvala, who later became a leader in the state Senate, said. “We were good friends for almost 50 years.”

At the time, Latvala said, the RPOF had a staff of fewer than 10. “We were practically a nonexistent political party,” he said. “I hired him because he was a hardworking young Republican.”

Pennington would serve as the RPOF’s executive director from 1980 to 1984. Latvala said he had held similar positions in a couple of other states, including Washington. He worked for Latvala’s Clearwater-based company, then called Direct Mail System, and made his mark as a consultant and strategist.

The company was ahead of the curve, pushing more Republican buy-in to absentee voting, said Mark Zubaly, who joined the company (now DMS) in the early 2000s.

“Rockie was ‘The Guy’ in the mid-1980s, heading Senate campaigns when the GOP had nine people in the state Senate,” Zubaly said. He remembers Pennington as a forceful personality, albeit one who preferred side conversations to center stage.

“He was kind of introverted but in a way fearless too,” Zubaly said. “If you were his client or his friend, he did what it took. He would never do anything half-assed.”

He was not afraid to tell candidates what they needed to hear.

“He had this reality check,” Zubaly said. “He could say, ‘Just because everyone is kissing your butt doesn’t mean you know everything — and if you don’t do this, you are going to lose.’ I saw him check some big people.”

Latvala recalled the same, and the memory brought up a chuckle. “He was blunt,” the former Senator said.

Roger Allan Pennington was born Aug. 16, 1952, in Charleston, West Virginia, the son of a pastor-farmer and a homemaker. After high school, he enrolled in Brevard Community College, where he met Jeannette Jones, and a spark was lit. They transferred to Florida State and married in 1974.

Politics became the landscape for much more, an art form that could inspire him to get up in the middle of the night to write political ads.

The direct mail firm grew to a staff of around 40, including production personnel. Latvala sold his interest in 1997, making Pennington the majority stockholder. He inspired the same creativity in colleagues that had served him so well, said Mike Milligan, the current majority partner.

“At meetings, he would listen and not talk,” Milligan said. “If you had a good idea, he would let you run with it. I can’t think of a time when somebody had an idea that at least had a chance of working out and they didn’t get to try it. He’d say, ‘OK, go do it.’”

Pennington started his travel blog in 2017, his yen for faraway places growing stronger by the year.

“People knew him as a force to be reckoned with, somebody you wanted on your side,” said Erin Miller, his daughter. “Those things are definitely true. But most people didn’t know the other side of Dad, that he was very kind and generous, that he was very detail-oriented and also traveled like that.

“He would say, ‘I just had tea with Tibetan monks!’ He would go to fermented yak milk festivals, things nobody would ever do, and make friends all over the world.”

Once, while searching for silverback gorillas in Uganda, he stumbled on an orphanage, which he continued to support financially in the years since.

“He saw the gorillas, too,” his daughter said.

Jeannette Pennington appreciated her husband’s passions but also her own limits.

“Mom would meet him in places like Hawaii and Japan,” Erin Pennington said. “She had no interest in trekking through the wilderness to remote places.”

For those destinations, he hired guides who knew the language and could steer him in the right direction. Those relationships led to more unplanned encounters, conversations with villagers in Africa, or the chance to attend a wedding in the jungle.

His itinerary was full as ever this month, but his health was not cooperating. Pennington contracted malaria in the Hindu Kush Mountains, his family said, a strain dubbed “super malaria” because the parasite resists conventional treatments. He planned to continue to Dubai but died in an Islamabad hospital.

“We are all grateful that he was on an adventure,” his daughter said. “That’s what he wanted to do, and it’s how he wanted to go out. And if getting super-malaria in Pakistan doesn’t (fit that bill), I don’t know what would.”

The news has traveled to friends in the Philippines, Indonesia, Nigeria and here. Rockie Pennington is survived by Jeannette, his wife of 49 years; daughter Erin Miller and her husband, Kenny; their daughters, Savannah and Charlotte; daughter Sara Nuvy and her husband, Zack; their sons, Finley and Parker; and his son, Ryan Pennington and his partner, Liz Bynum. A celebration of life will be held at a date to be determined.