Being the Best Damn Ski Bum You Can Be – Jay “Luigi” DeBaggis
Jay DeBaggis Shares How He Came to Breckenridge, Colorado and Why He Stayed
by Holly Battista-Resignolo
I have had the pleasure of knowing Jay DeBaggis for quite some time. I am pretty sure it was around the time my first child was born as Jay was working at the Peak 8 Children’s Center at the time. He was someone I really wanted to interview as his bright and enthusiastic nature has always warmed my heart.
It turns out that the Breckenridge Ski Resort’s Peak 8 Children’s Center was one of Jay’s first jobs, taking four and five year olds out of ski. He then moved on to Breck Ski School’s Kids Castle, teaching six to 12 year olds and got involved with the bombers program. Here he skied with the same kids every week. It’s a really good program, because you get the same kids, they all progress together. He then coached with Team Breckenridge for 15 years. He would typically get the youngest kids of five and six year olds, but they were all ripping hot skiers, you know, oh my god, yeah, because their parents all ski, and started when they were three, or whatever, and we had so much fun.
One of my favorite memories of Jay was seeing him come into the BSR Admin building dressed as Ripperoo. As we reminisced, Jay said, “ It’s funny how I got that job. A friend of mine who used to run Maggie, she had a wing and karaoke night. She had been at a party and came banging on my door later that night. She’s like, Jay, I need somebody to ski around in a chicken suit to promote my wing and karaoke night. She’s like, I’ll pay $150 for three hours. I’m like, I’ll do it. So I made a sign and said, Eat My Wings, only $1.50 a pound. And invariably, people would say how many wings are in a pound? I said they’re sold by weight, not volume.. It depends on how big they are. So anyway, at the end of the season, ski school had a race set up. That was the first year they had Ripperoo, and this kid named Fast Eddie was in the Ripperoo suit, and they’re like, let’s have a mascot race, the Dog against the Chicken. So we raced, and I beat him best two out of three. I never raced before, but I was a pretty good skier, and I’m like, wait a minute, your name’s “Fast Eddie”, and I just beat you. That makes me “Faster Eddie”. To this day, he still calls me “Fast Eddie”. I love that. Then, right then and there. Dave Bullcraft said, you want to be Ripperoo next year? I’m like, sure. I’ll do it!”
It turned out it was one of the funnest jobs ever. I was hanging out with all the kids, going through all the ski schools, high-fiving the kids. I used to ski Superpipe in that costume. It was crazy fun.
We moved away for a short period. When I got back I told my wife, I love kids. The Little Red Schoolhouse opened, and I got a job there. I was teaching there for a couple years. I had moved on to a new job but the guy who had been reading to the kids moved away, so I started coming in and reading to the four and five year olds. I’ve been doing that for 10 years. It’s awesome.
I try to fill their heads with positive ideas and remind them, “You guys are the future kings and queens of Breckenridge”. I taught them that Albert Einstein said, “Imagination is more important than knowledge”. I’m like, Do you guys know what imagination is? No, well, all right, close your eyes and pretend we’re going to the moon. We’re on a spaceship, and we’re flying to the moon and landing on the moon, and we’re jump-bouncing around, because Gravity’s not so good there. Knowledge is two plus two equals four. So imagine it. And now I can. I’ll ask him, I’ll say, raise your hand if you know what Albert Einstein said. And half the kids raised their hands. I love kids. They’re the future of the planet. God knows. They’re gonna need all the help they can get dealing with the planet. I believe we must have a positive impact on them.
Jay came to Breckenridge in 1986 from Cleveland, Ohio. He knew at an early age that he wanted to be a ski bum. I had a tragedy in my life. My older brother passed away, so I realized that life was too short. So I saved $1,000 drove to Breckenridge. And I had a buddy that lived here, but he was in Cleveland when I got here, so I didn’t know his soul.
I got to town with my stuff and sleeping bag. And, no, no, I had, um, I went to the end of town, which is the gas station then, and said, Where can I find a bed? And they sent me to the Fireside Inn. So that first night, I met a buddy, Chip, who I’m still friends with, and these two girls that had been here for a while, they had found a place, but it wasn’t gonna be ready for two weeks. So the management company gave them a place with two bedrooms and two beds in each bedroom, and they asked us if we want me and my buddy, Chip, who I just met, if we wanted to come and split the cost with them while we were looking for a place. So I stayed in a bed, breakfast one night, living with two girls and a guy, and then Chip and I found a place up on the baldy mountain townhomes, and the rest is history.
When I was in Junior High, my dad told me, “Son, you can be or do anything you set your mind to”. I thought about it for a long time because I thought it was really important. After about a year, I said, Dad, I think I know what I want to do. He’s like, what’s that? I Said, I want to be a Ski Bum. And he said, All right, then “be the best damn ski bum you can be“. That was his advice.
Good People Making a Difference in their Mountain Town Community: Jay DeBaggisWhen asked why he has made Breckenridgeridge his home, Jay pulled out his answers straight out of his pocket and laid it out on the table.
Jay’s List – What He Came To Breckenridge and Why He Stayed
#1 I was born to ski and the skiing here is pretty darn good!!
#2 Them people!! 95% of the people here are happy, healthy, active, educated and importantly, here because they want to be!#
3 The climate – summers rarely get above 80 degrees and there is little to no humidity + the winters are long and snow filled – the better to ski in!
#4 My lovely wife loves it here and all her friends are here.
#5 It is the closest place to heaven on earth. I have found it’s even physically closer!
#6 The plethora of things to do besides ski!! i.e. Mountain Biking, golfing (both ball and disk), hiking (world class), boating (on rivers & the reservoirs), motorcycling and just being outside.
#7 The community – again the people- are involved, willing to help and extraordinary.
That really does sum it up and we agree.
Jay DeBaggis is one of the Many People Making a Difference in Breckenridge, Colorado. Give him a high five when you see him!
As seen in Breckenridge Magazine Issue 10 2025: CLICK HERE to Read the Whole Magazine!
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