+ By Christine Fillat + Photos by Glenn A. Miller

John O’Leary is a man with a knack for finding way to get things done and making people happy. And he really, really likes St. Patrick’s Day.
He reminisces of a past St. Patrick’s Day spent with like-minded cronies—an impromptu, ragtag group walking up the middle of Main Street, carrying Irish flags in the spirit of Irish pride. Perhaps they were influenced by a spot of Irish liquid repast, but inspiration struck O’Leary that day—Annapolis needed a St. Patrick’s Day parade. Like the present-day parade’s route along West Street, Church Circle, and Main Street, the path getting there was not a straight line.
O’Leary, a salesman of artificial intelligence software systems for the federal government, grew up in Arnold, briefly attended the Naval Academy, served in the marines, and worked in the heady, early days of the Silicon Valley bubble. He’s married, with four children, and is the sort of fellow who thrives on bringing joy to other people. In 2008, he founded the nonprofit Warrior Events to give some relief to veterans he had met at Walter Reed National Military Medical Center who were recuperating from injuries and trauma suffered during the conflicts in Iraq and Afghanistan.

Proud Annapolitan.

Through Warrior Events, O’Leary would take veterans on visits to children’s hospitals, in places such as New York City, St. Jude’s in Memphis, Philadelphia, and locally. A particularly moving event took place in Boston, where the veterans visited civilians who were wounded in the Boston Marathon bombing. Connecting veterans who had lost limbs at war with innocent bystanders who had lost limbs from the marathon bombing was remarkable for everyone. The message from the veterans was, “You’re going to be okay.”
Warrior Events holds activities for recuperating veterans and their families throughout the year. It has evolved to support veterans in general, first responders, Gold Star families (families who have lost a child in war), and Gold Star mothers.
O’Leary initially thought that a St. Patrick’s Day parade could be a great way for the Warrior Events to generate funds. The first parade was in 2012, and Warrior Events ran it for two years, but, unfortunately, the event lost money.
“I said, wait a minute, that’s not why we have this nonprofit,” says O’Leary. So, in 2014, he created an LLC to run the parade and personally assumed all the risk involved. O’Leary christened his new venture Naptown Events. The parade is not a moneymaker. “The insurance policy is through the roof,” he says. With costs increasing every year, Naptown Events initiated a fundraiser, the Hooley, an Irish party involving music, which is held the night before the parade. The first Hooleys were at different downtown Annapolis hotels, with dinner and music by Dublin 5, O’Leary’s favorite local Irish rock band.
Parade day involves a lot of moving pieces. Each entry is considered a float, and 100 of them line up throughout the Murray Hill neighborhood. Many of the neighbors join in the fun, some supplying refreshments, portable toilets, and parties of their own.

O’Leary, founder and commissioner of the St. Patrick’s Day Parade, enjoying the smiles of the crowd.

“I used to be the town leprechaun,” says O’Leary. “I thought that was my responsibility, as being Johnny O, [who] puts this thing on. . . . I’d have a shot [of Jameson Irish whiskey] with every single person . . . before I got downtown.” Almost four years ago, he quit drinking and feels much better. “It’s more fun,” he says. “I see things I didn’t see before.”
From Murray Hill, the parade turns onto West Street. “There are so many people,” says O’Leary. “Then you turn down Main Street. That’s actually a good feeling, too, my favorite part. When you make that turn and you look down Main Street, and there’s soooo many people. You see the Bay out there, I see my tents, way out on the dock. It’s the best. People love it.”
Post-parade, Annapolis is crawling with people. The bars are packed, the businesses are doing well, people are generally happy, and it is a boon for the city. Previously, the party, with entertainment by Dublin 5, would continue at Armadillo’s, but nowadays, Naptown Events has two tents erected at City Dock.
The Annapolis St. Patrick’s Parade is now a three-day event. This year, the Hooley will be on Friday, March 15—it has been sold out since August. Shamrock the Dock, a ticketed music festival, will be on March 16 and after the parade on March 17—the actual holiday. It looks like it will be a heck of a party.
Naptown Events has generated something of an alternate career for O’Leary. The company contracts with the federal government, organizing graduations from large schools, changes of command, and retirements. O’Leary organized the stage, sound, cameras, and screens for Governor Wes Moore’s inauguration. He was also involved in Let’s Go Music Festival, which takes place at the Anne Arundel County Fairgrounds in Crownsville.
Going forward, O’Leary will have to adapt to the new plans for City Dock, including how its restructuring will affect Shamrock the Dock and where the festival will be sited. He will surely come up with a plan. After all, he knows how to get things done. 

For more information,
visit naptownevents.com/events.