On a late winter's day, John O’Leary is at a Starbucks in Annapolis. He’s driven up in a red, ‘54 Chevy pickup, one he bought way back in the early ’90s from someone in downtown Annapolis.
“I’ve owned that truck for half its life,” he said.
He’d be happy to talk about trucks. That’s just not why he’s here. It’s a bright, sunny morning, and O’Leary would be fine talking about the weather, too. Temperatures are in the 40s, and the forecast calls for a warmup all week.
If the forecast is right, it could be in the 60 by the weekend – and if O’Leary’s luck holds, that would be a glorious Sunday. It’s the kind of weather that makes you feel lucky to live in Annapolis.
Sunday is the day when thousands of people will descend on Annapolis for the 2022 St. Patrick’s Parade, the return of a spring tradition O’Leary started 10 years ago.
“Well, we didn’t have a parade in Annapolis, a St. Patrick’s Parade,” he said. “We celebrate St. Patrick’s Day with gusto, right? I mean, but more from an American version of St. Patrick’s Day. It’s a drinking party. Very little Irish heritage was being celebrated that day.
“And so, I wanted to bring a parade to town that was, first of all, a well-done parade.”
By that measure, O’Leary is a success. Maybe even one of the most successful celebrations in Annapolis history. Annapolis is a city that loves a party – yeah, there will be American-style drinking on Sunday – and O’Leary is the creator of one of the biggest on the calendar.
Part of that is timing. It’s two weeks before the actual holiday, marking the death of the missionary who brought Catholicism to Ireland in the 5th century. The most famous parades are in Dublin, Boston and New York on the actual holiday itself, March 17. Washington and Baltimore are on that day too.
Yet an early date always pays off for Annapolis in emerald and plaid, attracting bagpipe bands looking for extra events. Annapolis features as many as a dozen pipe bands in a single year.
It also is something about this time of year, the cusp of spring. Sure, there could be a snowstorm in March. It happens.
But attending the Annapolis parade is like joining a big happy coming out party to mark the end of hibernation. The weather suddenly feels so different from the cold and damp of January and February that it can be like discovering spring before anyone else is in on the secret. The days are surprisingly longer too, with the equinox only weeks away. It’s the time of year when you look around at 5 p.m. and suddenly realize it’s not dark yet.
To be outside on a perfect day in March is to be alive. Nature seems to agree. It has not rained on a single Annapolis St. Patrick’s Parade since O’Leary stepped off at the head of the first one back in 2012.
O’Leary understands the draw to be in a happy crowd. He’s always been something of a party planner, even back at Broadneck High School.
“I like to put people together,” O’Leary said. “I get excited about making people happy and bringing people together. That was a huge depressing thing with COVID. You couldn’t do that.”
Depressing because the Annapolis St. Patrick’s Parade was last held in March 2020 – under a perfect sky with temperatures in the mid-60s – days before the COVID shutdowns arrived in an attempt to ward off death.
That parade, a huge deal by any standard in Annapolis, was the biggest St. Patrick’s parade in the world that year – the giant parades all canceled days later out of fear of becoming a super spreader event.
“That is a true statement…” O'Leary said. “The big ones are normally on St. Patrick’s Day. By St. Patrick’s Day, this world was shut down.”
If you look back, that St. Patrick’s Parade was the last normal thing in Annapolis before the world went nuts. COVID killed more than 900,000 in this country and almost 6 million worldwide. An insurrection happened at the Capitol in Washington, abetted by a sitting president trying to stay in power. Russia invaded Urkraine.
People picked one side or the other, mad about being told to get vaccines and wear masks or mad about people who refuse to get a vaccine or wear a mask. People are mad about the insurrection or mad that you’re calling it an insurrection.
Things have changed for O’Leary too. He is vaxxed and boosted but got COVID anyway – just the sniffles, so he’s grateful he went with the science.
He changed jobs. He sells artificial intelligence/machine learning software to the military, hoping it will see advantages for its procurement system.
And, in a big thing for someone who is the face of an admittedly beer-filled parade and accompanying party known as the Annapolis Hooley, he quit drinking.
“I quit drinking after about three months of COVID. I mean, it was too hard to drink and do COVID for me,” O'Leary said.
Like much of America, his firm stopped traveling. He went from meeting with admirals and captains and colonels over coffee to video conferences. Unlike everyone else doing this, he talked often to a blank screen – rank and file military laptops don’t allow video feeds without security clearance.
“Anyway, it was just rough because I'm a very social person,” O’Leary said. "And I was working out of my greenhouse, and it was not good, healthwise for me. So I made a decision to quit drinking and take control over my life.”
At age 50, the impact was dramatic. O’Leary admits to being unhealthy until his decision. Afterward, he lost 35 pounds, his systolic blood pressure dropped 50 points and he started to get in better shape. He says it allowed him to open up and look around.
His friends were used to John the guy who has a few and then gets up and sings “Fishermen's Blues” with the Irish rock band Dublin 5. They were worried he might go “nuclear” during the stressful months of planning the biggest spring party in Annapolis.
“That was my fear, right? I'm John O'Leary, the leprechaun of Annapolis, right? What's the town going to think if I quit drinking?” O’Leary said. “Then I woke up and got mature, and I was like, well, who cares if I quit drinking? I can still do all that stuff.”
After months of sobriety, he found his voice. Travel is back on at work – he just got back from a conference in Las Vegas. He’s comfortable with being the life of the party, again.
“And now I don't have any trouble getting up on stage and singing the song…” O’Leary said. “I love it. It’s fun and it gets people going.”
That’s what O’Leary did in creating the Annapolis St. Patrick’s Parade.
Although selling software has long paid the bills – today, he works for a 10-year-old startup called DataRobot – he started a nonprofit called Warrior Events in 2008. It supports wounded soldiers and their families shifting to civilian life.
The nonprofit reflects O’Leary’s service. After high school, he enlisted in the Marines. A few years on, he became one of just a handful of enlisted Marines and sailors selected to attend the Naval Academy.
It’s a big honor, but O'Leary admits it was too much. He didn’t graduate, saying the age difference with other mids and a lack of ability as a student convinced him to go back to the Corps. Looking back, he thinks he should have stuck it out.
He came back to the academy through marriage. His wife is a retired Navy officer who graduated from Annapolis in 1995. Together they have four children.
Warrior Events grew to support first-responders and Gold Star Families and the community in general. It started a food drive that bought 10,000 hot meals from city restaurants struggling to stay open during the pandemic. It donated to first responders and healthcare workers first, and when they didn’t need them anymore, to people suddenly without jobs.
When O'Leary started thinking about a St. Patrick’s parade, Wounded Warriors was the underlying purpose. Wounded veterans have always been part of the parade, and money raised from sponsors and other events benefits the nonprofit programs.
There was another motivation. O’Leary also wanted to help Annapolis businesses in a traditional dead spot on the calendar. He used to work in a downtown restaurant, so he understands the pressures when times are slow.
Those first two parades, 2012 and 2013, were rough. O’Leary had to figure out how to throw a parade in Annapolis. It was not cheap. It cost $10,000 in city for services such as police and fire. Then there are public toilets stations to rent and parking to pay for, buses to charter to connect the parking with the parade route, and clean-up. There is insurance.
The parade lost money. Two years running. O’Leary covered the costs himself.
“Warrior Events had money in the bank. But, wait, I can't use donations to throw a party for the city. It's not the mission of Warrior Events," he said. And because of that, I created Naptown Events LLC to take on the burden of the parade.”
The events company fit his identity as the high school party planner and now stages other functions – it recently covered City Dock in a tent for a private party. It’s helped straighten out the cost of the parade.
Leading up to 2020, O’Leary said the Annapolis St. Patrick’s Parade became a financial success. Fundraisers helped, and after costs were covered, leftover money went to Warrior Events and its programs. There was enough money left over to donate $10,000 in 2020.
The parade accepted anyone who wanted to march that first year, except political candidates. That ban never changed. It got a lot of pushback from candidates used to throwing out buttons and shaking hands while marching.
Top elected officials can participate as long as they leave campaign trinkets and slogans at home. That was hard, too. He had to tell at least one elected official point-blank: You're welcome, but this is an Irish parade and no one wants to see your stuff. Now, he says, almost everyone gets it.
“A few years in, everyone is like, ‘that’s great, this is fantastic,’” O’Leary said. “The Fourth of July parade was just nothing but candidates this year.”
High school and college bands are encouraged – but this isn’t football season, so band members tend to take their uniforms out of storage for the parade. Nonprofits are a recurring feature, with some groups using their parade entry to raise funds for their own causes.
Some participants have been there from the start. The Naval Academy Band returns every year. Businesses owned by the extended Kelly family of Annapolis, Kelly Electric, Navel Bagels and others have been there from the start. There is a lot of turnover this year, it's hard coming back from a year off, but O'Leary considers that exciting.
This year’s grand marshal, the honorary head of the parade, is longtime lead sponsor Steve Kelly of Kelly Electric.
“We just couldn’t do it without them,” O'Leary said.
O’Leary is strict about having good floats. He knows the parade is a great marketing opportunity, but he wants a float that shows work.
“We want Irish floats,” he said. “We want people to put some effort in their floats, and not just have their logo’d-up truck driving in the street.
What's a good float?
One with lots of color. One with a theme. One with costumes.
“One that makes people say, hey, good idea. That’s good,” O’Leary said. “You can tell they put some effort into it.”
Pipe and drum bands are the parade heartbeat. They keep the rhythm going. Even if you can’t stand the wail of a bagpipe or the pounding of the drums, seeing the kilted ranks go by is a memorable moment – you can feel it. They know it too, charging as much as $5,000 to march.
O’Leary’s goal is to have one bagpipe band every 10 floats, although he won’t make that this year. Many pipe bands are the creations of New York and Massachusetts fire companies.
COVID, still putting extreme pressure on first responders and the health care system, made it impossible for many of those groups to keep the tradition alive this year – or worse.
“That's actually due to the virus,” O'Leary said. “The virus has kind of decimated their ranks.”
Once O’Leary sets the lineup, he and a team of parade marshals work on making the day go as smoothly as possible. There is coordination with the city and its emergency services in case something goes wrong, maps to study and placement to work out.
The job got a lot easier when Ben Sale came on as lead marshal. Sale, chairman of the city Planning Commission, is a Navy vet who also is the captain of a Mardi Gras parade float krewe back in his boyhood hometown, New Orleans.
“He knows what's going on,” O’Leary said.
The marshals help organize but they really keep the parade running smoothly. They make sure kids aren’t running into the street and close any gaps between floats.
O’Leary was out there doing that too, those first few years. Now, he says his job is shaking hands and meeting with the governor.
They have fun, but it’s a big endeavor. It involves endless planning meetings and one big dinner just before the event to take a final run-through. On parade day, you won’t see marshals wearing green leprechaun hats or wild green shirts. They’re all in very serious tweeds.
“So that's the other thing with my marshals,” O’Leary said. “Half of them are former military, so they don't fuck around. And guess what? None of them do.”
When Sunday arrives, O’Leary will arrive early at the lineup spot on Amos Garrett Boulevard. There are lots of things to do, lots of chaos to sort out before the parade starts at 1 p.m.
“The lineup is nuts. Everyone should be in place by about noon. It’s an orchestration that we manage,” O'Leary said.
All of it flows from those planning meetings, understanding who is doing what is crucial to getting everyone in the right spot at the right time.
“We coordinate when they should show up, what road they should go down. Everyone is aware of a script – an orchestrated script – of where they should be turning, who they’re with, what numbers are in their windshield so that when they roll in, they don’t get interviewed again. Then we get them in place and they get their floats finalized.”
O’Leary has more hands to shake, too. This year, he has invites to six different house parties in the Murray Hill neighborhood behind the lineup spot.
By 2020, the parade was attracting crowds from as far as Connecticut, Mississippi, California and Texas. A group of Norwegians O’Leary met in a volunteer disaster clean-up came every year.
Two years ago, even as all this preparation and coordination was happening, it was different, too. O’Leary knew the parade would be a close thing. COVID showed up in the United States on Jan. 20. The first cases in Maryland showed up on Feb. 20.
Parade day 2020 was a beautiful afternoon. Brilliant sunshine, temperatures in the 60s. A day that made you feel you had just discovered spring. Crowds of happy people lined the route down West and Main streets.
There was lots of green. There was beer in the streets, but it wasn't mayhem; it was just merry.
“It was as if people were thinking it was … the last thing that they were going to do, almost," O'Leary said. "I don't think that was on my mind. We knew this COVID was coming. But we didn't know what was going to happen.
“You know… we thought we would be back. I didn’t find out until later that the city was really close to shutting it down but didn’t tell me about that.”
The COVID numbers show it was the right call. Contract tracing and infection numbers found no sign the parade spread the virus.
“If there was a superspreader event, I was the superspreader. I hugged and kissed so many people that day,” O’Leary said. “It was awesome. It was awesome.”
Then 2021 was called off. First, it was postponed to September, then just canceled for the year.
This year, the parade will probably lose money again. The city has waived many of the fees after the 2020 cancelation, but O’Leary knows he’ll pull money out of his pocket to cover the difference. He wishes more downtown businesses supported the parade, but says it with a sigh that's a sign he understands their problems.
The Norwegians aren’t coming this year. The pandemic devastated their economy and most of the group are unemployed. O’Leary offered to help pay for their trip, but they told him they wouldn’t feel right about accepting it while being on unemployment.
The parade starts at 1 p.m. Sunday, By 4 p.m. or so, it's all over for another year. Hopefully, just another year.
At the end, O’Leary knows he’ll go back to work selling to the Navy, trying to get it to buy his software as a way to help fix the procurement system. He likes to explain it as a way to predict the future, foresee problems and head them off.
As he steps off at the front of the parade Sunday – sporting a tweed jacket, a bowler hat and a green sash as the symbol of the St. Patrick's in Annapolis – he‘ll take mental pictures of the crowd. It’s what he remembers most from 2020. It's what he missed most last year. It’s what he’ll use to keep him going as he starts the work to bring the parade back in 2023.
“That's the best part of my job. It's going down and seeing all the smiling faces,” O’Leary said. “There are some happy people that day. I mean, every, every year, but that's what I remember.”