Tuesday night brought a first for Jim Bailey.
When his youngest daughter shared the dates for an upcoming event at Penn State University, Bailey didn’t hesitate.
There was no checking his calendar, no assuming his wife, Donna, would handle the arrangements.
Instead, he immediately sent a text to his daughter saying, “We’ll be there.”
It was a good feeling, said Bailey, publisher of the Daily Record since 1975.
One he’s planning to experience more often.
Wednesday morning, Bailey gathered his staff to announce he had sold the 104-year-old family newspaper to Matt Walsh, CEO and owner of Observer Media Group Inc. in Sarasota.
Over four decades, the third-generation owner piloted the Daily Record from hot type to computers, through good and bad economic times and into the internet age.
It required long hours, including many nights of sleeping on a light table early in his career. Coupled with his staunch dedication to the community, Bailey routinely piled up 60 to 70 hours a week.
“I don’t recall any time he was asked to participate and he turned anybody down,” said City Council member Bill Gulliford. “He’s a great asset.”
Fourth Judicial Circuit Chief Judge Mark Mahon called him “an icon in our community.”
Bailey said he will remain active in the city, including continuing as chair of the Downtown Investment Authority. He’ll also pursue business consulting and investment opportunities.
It took finding the right buyer that would protect his family’s legacy for Bailey to make the decision to move on.
Memories of his newspaper career
Over the years, Bailey has received many inquiries about selling the newspaper. He and Walsh even came close to a deal in October 2015. (They also talked when Bailey ran for mayor in 2010.)
Bailey has six daughters, none of whom are involved in the business. Plus, he didn’t have a succession plan.
“It was important to me that the business continued and thrived the way it has all these years,” Bailey said. “I don’t think there’s anybody better than Matt.”
Walsh owns 10 weekly newspapers and has an editorial background in journalism, including at the Miami Herald and Florida Trend. He previously bought the Tampa Bay Review from Bailey in 2001.
He said Bailey initiated another conversation about the Daily Record at the end of 2016.
Walsh said he was impressed Bailey had built a niche with very few competitors.
He said it showed Bailey and the staff had been satisfying customers, who found no reason to try to find someone else to do business with.
Walsh said during the latest talks he detected a sense that Bailey “wanted to make it happen.”
However, Walsh said he wasn’t completely sure the deal was going through until Tuesday — when the check cleared.
Bailey said the two originally planned to tell employees today.
“We got everything done and we looked at each other and said, ‘Do we really need to wait?’” he said Wednesday.
There was a concern the news would get out early if they waited until today. And Bailey wanted it on the front page of the Daily Record before that could happen.
Bailey said he wasn’t emotional about selling the business until the staff meeting. Before then, he had enjoyed the negotiating process.
But, he said, “To get out there and see the faces, that’s probably when it hit me.”
Bailey later described the newspaper business as one of the most stressful there is.
“You have to be perfect all the time because the cost is so high if you’re wrong about somebody’s life,” he said.
And when a staff is totally accurate, he said, “You finish up and feel relief about 15 minutes and you’re starting over again.”
Bailey has countless special memories, including writing about his father’s passing in 2010 and the 2012 murder of Dale Regan, head of The Episcopal School of Jacksonville, with whom Bailey was close.
He said writing about them helped him through the ordeals.
Bailey believes his father, James F. Bailey Sr., would be “very, very, very proud” of how he’s run the business and how the sale was handled.
Lasting impact in community
Hours after the announcement to the staff, Bailey was in the office he’ll retain in the building at 10 N. Newnan St.
A consistent stream of text message notifications came from his cellphone, evidence of how the community appreciated his contributions.
Gulliford said in an interview that Bailey’s biggest impact was the fact he has always been there. He’s worked with Bailey on issues throughout the years, including trying to save the Seminole Club Downtown and addressing issues with Hemming Park.
He said Bailey doesn’t have a reason now not to run for council. “I’m going to chastise him,” Gulliford joked.
Mahon said Bailey has always been honest and straight-forward. “He’s a real asset and an incredible gem,” he said.
Chris Hand, chief of staff to former Mayor Alvin Brown, said the community owes Bailey and his family a debt of gratitude.
“For the last century, they have provided not only a must-read newspaper but also key support for Jacksonville’s legal, business and Downtown communities,” he said.
Hand said Northeast Florida will continue to benefit from Bailey’s public service and civic involvement.
“I look forward to seeing what new ventures and initiatives he and Donna pursue next,” Hand said.
Bailey said that won’t include starting another business. He doesn’t want to create something that could tie him down.
Not having to rush back home
Bailey pointed out he hasn’t retired. He sold a business, one he said he couldn’t continue to provide the kind of energy it needed.
He has other business interests, including cattle in Georgia, real estate investments and honeybees in Jacksonville.
“I want to do some things and have some fun,” he said. “Yet, I’ll probably be in here (his office) every day.”
But, he will definitely spend more time with his wife, daughters and three grandchildren, soon to be four. He’ll also spend time with his mother, who still resides in the Jacksonville area.
Bailey’s looking forward to taking a trip with Donna to visit one of his daughters and then her parents.
“I’ve never gotten in a car and just drove for leisure,” he said.
That includes a previous visit to see one of his daughters.
“The last time I did that I went straight there as quick as I could,” he said. “The whole time I’m somewhere, I’m thinking about getting back.”
The upcoming trip will be different.
“I don’t want to think about getting back,” he said.
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