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$411,000 NIL-valued Reed Sheppard makes bold money move as Kentucky star signs partnership with WinStar Farm: "Life is good"

Fresh from his most impressive performance of the season against Mississippi State, Kentucky guard Reed Sheppard snagged another impressive NIL deal that will swell what is already a considerable NIL portfolio.

Sheppard recently signed an NIL deal with WinStar Farm to champion the racehorse named Life is Good. The CEO of WinStar Farm Elliott Walden released a statement praising the $411,000 NIL-valued Kentucky freshman (according to On3).

“Reed Sheppard is all about what we believe in at WinStar – being a good teammate (partner), conducting himself with humility and giving 100% in all he does,” Walden said. “We think he is a great fit for Life Is Good and WinStar Farm.”

The stallion Life is Good has won nine of its twelve competitive races and recently won the prestigious Breeders’ Cup Dirt Mile, which had a purse of $1 million, bringing its total career earnings to $4,541,700.

"Horses and basketball. Life is good," Reed captioned his Instagram post.

Reed Sheppard's Instagram
Reed Sheppard's Instagram

John Calipari keeps Reed Sheppard in check

Kentucky coach John Calipari has kept his praise of Reed Sheppard at a minimum, and while he celebrated the freshman's winner at Mississippi State, he had no idea just how impressive a game the talented freshman had.

Calling into Tom Leach's show, Calipari revealed Sheppard's mindset that made him such a good player.

“Until I got on the plane, I didn’t know he had 32,” Calipari said. “He has the ability to stay calm and not worry about losing. You only worry about winning. How do we win? You can’t play not to lose.”

Calipari has been under pressure to start both Rob Dillingham and Reed Sheppard, a proposition he has been reluctant to take up.

During his call-in, he pointed out that he would not be pressured to start the duo together and he would rotate as he saw fit.

“But starting, it doesn’t matter," Calipari said. "I mean, I think Reed, and if Robert didn’t foul, would have played the most minutes, so it doesn’t matter. I’ve got a group of guys and got to keep them on the same page. (I’m) trying to build up every young person and try to make sure they know I believe in him, but you hold them accountable.
“They’re responsible, and they own their performance. If we need someone who’s going to rebound better, then you may be out.”

Having the sort of firepower that John Calipari has at his disposal including the enigmatic freshman Justin Edwards at his disposal will make the No. 15 Kentucky Wildcats (21-8, 11-5 Southeastern Conference) a tricky opponent for any team during the NCAA Tournament.

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