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Haley Dillon: Mayor of Southie

Watch out Marty Walsh, there’s a new mayor in town!

After raising a whopping $17,566 for the 2019 St. Patrick’s Day Parade, Haley Dillion was named the official Mayor of Southie on Tuesday night at a very packed Roza Lyons. Parade organizers, the South Boston Allied War Veterans Council announced last year that the competition was back after several years’ absence. Four residents announced their candidacy and a total of $34,881 was raised for the parade.

Dillon, 24, is a life-long resident of South Boston and we sat down with her for a little Q&A about her experience.

What was the hardest thing about the race? 
Not knowing where you stand in the race. The whole time you don’t know if you’re $50 ahead or $1000 behind. This also made the competition a lot more fun! 

Which fundraising technique was the biggest money maker? 
Honestly getting involved with local businesses in our community made the biggest difference. We come from a town that is so generous.  I learned that all you have to do is ask for help and support and there will be people ready to help. So many businesses owners from City Point to the Seaport helped me. I remember the first day, when I was trying to get donations from business that I wasn’t already friendly with, I got three “call back later” answers. My fourth call was to Tuscan Kitchen down in the Seaport. The hostess put me directly on the phone with Charlie the GM and I didn’t even get to finish asking for a donation and he was already saying, “Absolutely!” It honestly made gave me confidence to keep asking other businesses that I wasn’t too familiar with for help. 

How many events total did you have?
Sparkle Night at L Street Tavern Hosted by Susan Woods
Amrheins Night
Lazy Jack Paint Night at the Broadway. 
Bowling at Southie Bowl
Cornhole competition donated by the Perkins Post 
Kings Seaport Bowling event

What are you most excited about?
I’m so excited that I could help my community fund such an amazing event like the parade. My best friend Allison runs the Kick Off For Kids fundraiser every year and she encouraged me to run for mayor. I saw how much her fundraiser helped Southie’s youth and I was so ready to do my part to help our community.

Have you picked your mayoral court?
Yes! I picked my life long friends!  We’ve never missed a parade day!

Haley also asked that her mom – the amazing Betty Dillon -get a special shout out. “She was there for me at every event setting everything up perfectly and in place while I was rushing around before every event. She was the true back bone of this race and I couldn’t have done it without her!”

Look for Mayor Dillon at the beginning of the parade as part of the Royal Court. The parade begins at 1pm on Sunday, March 17th.

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About the Author

Maureen Dahill

Maureen Dahill is the editor of Caught in Southie and a lifelong resident of South Boston sometimes mistaken for a yuppie. Hockey mom, yoga enthusiast, lover of red wine and binge watching TV series. Mrs. Peter G. Follow her @MaureenCaught.