A different family reunion – like literally!

Glens Falls Economic Development Director Jeff Flagg seems to be reflecting as the “Flagapalooza!” family reunion at my home last week was winding down. He is flanked by his soon-to-be great nephew Darnell, 4.

I don’t know there’s such a thing as a perfect day, but a family reunion held at my home last Wednesday – for a family that isn’t even mine – came pretty close.

It featured perfect weather to be poolside, kids playing and swimming, adults eating and drinking and some spirited cornhole contests.

There were family members catching up, some reminiscing – and one who was holding court from the head of a table – all day long.

And the non-family members like me were meeting the family, including six kids ranging from 5 to 10 years old – who politely shook my hand when I met their acquaintance.

The family, about 20 of them, belongs to City Economic Development Director Jeff Flagg, whom I met through a mutual friend at least a decade ago.

Jeff is a character. He’s funny, smart, quirky and just fun to be around. So when he told me his family was coming to town from Colorado, Georgia and Ohio, of course I offered to host a gathering.

I’d met his brothers, but none of the extended family of wives, nieces, nephews and their kids – and “The Flaggman” Warren Flagg – whose claim to fame in recent time was working on the defense team for admonished NBA referee Tim Donaghy, featured on Netflix.

I’m a curious guy by nature, a people-watching fan and a writer, and I knew this was a great opportunity for all three.

When they arrived, they were met with a “FLAGAPALOOZA!” sign draped across the front of my garage. I painted it hours earlier and one friend thought I had purchased it, so apparently it looked OK.

Only a few photos were taken this day, but as they were leaving, one Flagg family member decided to snap one of the sign I made. (Side note, a neighbor at the end of the street stopped to ask the caterers what “Flaggapalooza” was!)

For me, it was one of those rare days where I felt I mixed well and talked to everyone – eagerly. One niece told me she had wanted to be a journalist and is now in marketing. I loved the passion for journalism we shared in that chat. The two nephews were both former military men, super polite, sports fans and also really fun to speak with.

I spoke to the wives of the four Flagg brothers too, and got some different insight on their fun, unique families.  

And the friends exposed to “The Flaggman” got decades of stories from his life as an FBI detective and private investigator, including how he had to help recover bodies from the doomed Flight 800 that crashed off Long Island in 1996. He relished the new audience!

Retired FBI agent Warren “The Flaggman” Flagg poses for a shot with his nephew, Kyle.

I have to say, though, perhaps the highlight for me was playing ball in the pool with the little kids. We play a game called “Keep it Up,” where the object is to see how many times we can hit the beach ball without it splashing down. Initially, my wife and I were the only adults in the pool playing with the kids until another couple joined us.

Maybe we were reminiscing back to when our kids and their friends were always in the pool.

Maybe we just wanted to play!

Jeff Flagg’s great nephew Colin happily exits the pool area, probably headed for a s’more in the backyard.

The two kids who didn’t play but were content to be swimming and jumping off the diving board were 5-year-old Maya and 4-year-old Darnell. They are siblings who are in the process of being adopted by one of Flagg’s nieces and her husband. They were born to a drug-addicted mom and were socially stunted for a while, Jeff told me.

You wouldn’t have known it on this day. Maya, who was so cute and chatty and who could have asked for my house and I would have given it to her, kept dunking herself under water saying “I’m disappearing!” She’d then pop back up with a huge smile – and do it again.

So, I did it too.

And she howled and flashed her amazing smile.

Her brother was shivering along the side of the pool with an old orange life vest around his neck, but refused to stop jumping in. It was just too much fun apparently.

I loved how happy everyone was. No drama, aside from “The Flaggman’s” stories. Everyone was having so much fun there were almost no pictures taken(the family literally sent me the four that are featured in this). I took none, because my phone was playing tunes all day on the porch. Jeff said he kind of liked that nobody was snapping pictures because it indicated how caught up in the fun they were.

I like that too.

And everyone got even happier when the food came out!

Flagg had hired local barbecue master Andrew Prunty to drive his smoker to the house, and finish off a bunch of ribs, brisket and chicken that had been smoking for hours. People were blown away by the Louisiana native’s skills on the grill and with the fixins that included macaroni and cheese, cornbread, greens, potato salad and some killer beans.

Everyone raved, and Prunty, who calls his business “Soulfully Delightful,” ate up the praise.  

Post dinner, there was more drinking, a bonfire for smores and more swimming.

I jokingly told members of the Flagg family that I felt like an honorary Flagg that day. I got to meet Flagg’s parents years ago, at Fenimore’s Pub in Glens Falls. They have since passed, but I know they were characters too. Hopefully, if they were checking this shindig out, they wouldn’t mind adding a poser Flagg to the already very large Flagg clan.

I felt like family that day.

2 responses to “A different family reunion – like literally!”

  1. Thank you Dave…as the one of “the” matriarchs of the Flagg family…I say YOU are officially part of the family. What a lovely story! Linda Flagg

    1. Glad you liked it Linda. What a cool day!

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About Me

I’m Dave, an award-winning journalist turned journalism professor at Vermont State University at Castleton. Check out some of my latest articles!