How Olivia Prewitt went from “Future Mrs. Cousins” to Miss Kentucky Teen USA

Olivia Prewitt


The first time I really met Oliva Prewitt was when she was 12 years old and had somewhat of a dream come true experience with Kentucky star DeMarcus Cousins.

Prewitt was a huge Cousins fan and her mother found out that he would be at the John Calipari ProCamp. That was not long after Cousins had been the No. 5 pick in the NBA draft after Olivia finished middle school cheerleading practice her mother, Jamie Prewitt, had promised to take her from Danville to Lexington to see if there was any chance they might see Cousins.

Olivia had a special blue T-shirt printed that said, “The Future Mrs. Cousins,” on the front.

Once they got to Lexington, fate somehow intervened and Cousins drove by the Memorial Coliseum parking lot where they were and stopped. When Olivia told him she had come all the way to Lexington just to see him, Cousins even got out of the truck to talk to her and her younger brother.

But the story gets even better. They followed Cousins to Wildcat Lodge and coach John Calipari and John Wall came out. Wall also posed for pictures with them.

“DeMarcus also told Olivia he would be back for her in six years when she was 18,” Jamie Ryan said. “When he pulled out to finally leave, he blew her a good-bye kiss. It was a special moment and one my family will never forget. It was just something that was meant to be because I wouldn’t even want to guess what the odds were against us even seeing him.”

Maybe the odds were about the same as six years later becoming Miss Teen Kentucky USA. Yet that is just what Prewitt, a contributor the last two years, did Saturday. It came as no surprise to former Miss Kentucky USA Maria Montgomery, another Danvillian, that Prewitt won.

Maria Montgomery with Olivia Prewitt in 2010.

“I have known Olivia since she was teeny tiny when we both went to church together in Danville. Her family quickly became close family friends with mine. It has been so special getting to mentor her as she has grown up over the years,” Montgomery said.

“The Miss Kentucky USA pageant came to Centre College in Danville in 2010 when I was giving up my title. She wanted to be involved and so she and her Girl Scout troop helped with various things throughout. She just wanted to simply be there any way she could, which was just so sweet.

“I’ll never forget how just simply having a sparkly thing on my head made ears open to allow me to speak and influence girls at that age, which was one of my main goals of being Miss Kentucky USA. So now, I am more than grateful that she herself is wearing the teen version of my crown! She has truly accomplished one of her biggest goals! She worked very hard for the title and I knew she could do it.”

Montgomery didn’t get to go to the pageant because she now joins former Wildcat Ravi Moss on the Rupp Arena court to help get the crowd more engaged at Kentucky basketball games. But while Kentucky was beating South Carolina, Montgomery was checking for pageant updates.

“Olivia has a genuine heart of gold that warms everyone she comes across. She is exactly the type of girl we need representing the Miss Universe Organization pageant system because she is going to be the perfect role model for so many girls,” Montgomery said.

“I’m so excited for our mutual hometown Danville for getting it in the spotlight again. They were extremely supportive of me when I was heading to compete at Miss USA and I know they will do the same for Olivia as she heads to Miss Teen USA and as she represents our state through the year.”

Montgomery also spent some time as a contributor and I knew for years how much she thought of Prewitt. But I also knew how much Prewitt appreciated being around Montgomery and having her as a coach/mentor for pageants.

Olivia Prewitt with ESPN’s Kaylee Hartung

Prewitt wants a sports media career. She’s done videos, stories and photos for my blog as well as one of her own. She’s co-hosted radio shows with me and interviewed some of the nation’s best high school basketball players.

I could not be more proud of her for what she has done and what lies ahead. She’s truly a terrific young lady — just like Montgomery — and will be spending the next four years at the University of Kentucky.

Will she still be a contributor? Well, I hope so but with a crown on her head, she might have outgrown me and I could not be prouder.

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And just for those wondering, Cousins has remained friends and stayed in touch with Prewitt during his NBA career.

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