The biggest ‘what-if’ of Kentucky’s basketball season? He’s putting up big NBA numbers.

With five-star freshmen Chris Livingston and Cason Wallace sitting beside him, John Calipari was in the process of recapping Kentucky’s final loss of the 2022-23 season last week when he began dwelling on the missed opportunities that had ousted his Cats from the NCAA Tournament.

UK’s coach lamented that his team couldn’t manage a victory over Kansas State in the second round of March Madness despite outrebounding the purple Wildcats 44-25, committing just five turnovers in the second half, and getting the kind of play he wanted from the two teenagers seated next to him and reigning national player of the year Oscar Tshiebwe.

“These two play the way they do. Oscar plays the way he does,” Calipari said. “You needed one more guy to play and go get baskets, and play with that swagger that you have to play with in this tournament.”

Kentucky didn’t have that guy on that particular Sunday afternoon against Kansas State.

But that guy might very well have been on Calipari’s projected 2022-23 roster at this time last year.

Shaedon Sharpe joined the Wildcats in the middle of the 2021-22 campaign with the stated intention of practicing with the team and then making his debut — as one of the most-hyped prospects in all of basketball — the following season.

That obviously didn’t happen, as no one who followed the saga needs reminding. Sharpe did indeed practice with the Cats to close out last season but ultimately went through the NBA Draft process, kept his name in the pool, and was selected with the No. 7 overall pick by the Portland Trail Blazers.

It turned out to be a fine career move for Sharpe, but it resulted in scrambled 2022-23 plans for Calipari, who was banking on Sharpe to return to Lexington for a full season and become a major part of the Kentucky roster, with advisers in the young player’s camp signaling — both publicly and privately — that he would indeed be back with UK, pretty much all the way up until the announcement that he wouldn’t.

As Kentucky’s season went through an odd series of ebbs and flows — a far cry from the preseason expectations of a Final Four appearance — UK fans paying attention to the NBA highlights were left with a bad case of the “what-ifs” as they watched Sharpe throw down a series of “SportsCenter”-worthy dunks on a seemingly regular basis.

Sharpe’s reputation as a recruit was that of an advanced scorer with the size, length and elite athleticism to be a dynamic, instant-impact player on both sides of the court. Kentucky had no one else like him on this past season’s team, and — by the time it became clear he wouldn’t be returning to Lexington — it was far too late to try and find a comparable talent through the recruiting process or via the transfer portal.

UK ultimately added just one transfer last offseason: Antonio Reeves, a gifted backcourt scorer who had played three seasons at Illinois State but was not considered to be one of the top 25 players in the portal. Reeves ultimately found his way at UK, cemented himself as the Cats’ top offensive player on the perimeter, and helped lift the team to some memorable victories.

Reeves had a game-high 22 points — and made five three-pointers — in the Cats’ first-round NCAA Tournament win over Providence, but he missed the first 14 shots he took in UK’s loss to Kansas State two days later, finishing 1-for-15 from the field and 1-for-10 from three-point range.

“Every time he has the ball, we want him to shoot,” senior guard CJ Fredrick said afterward. “And he’s had a tremendous season. I’ll tell him — and he knows — that kind of stuff happens. But he’s been tremendous for us all season. You can’t fault him for one game. … It was just a fluke game.”

Calipari had similar words after the K-State loss, though he noted how badly UK needed the points.

“In these kind of games, you’ve got to make those shots,” he said. “You’ve got to make baskets.”

Reeves helped Kentucky win enough games that he can’t be blamed for any one loss. With Sahvir Wheeler out, Fredrick reeling from a painful rib injury and Wallace also playing through a series of injuries, the offensive load often fell on Reeves, especially toward the end of the season.

Sharpe’s presence, obviously, would have gone a long way toward easing that burden.

Shaedon Sharpe in the NBA

Those who looked past the highlights and watched the actual games likely found Sharpe to be a dynamic prospect with a ton of potential for the Blazers but a player still learning the finer points. At the beginning of the season, at least.

For every highlight-reel dunk in the early going, there was a missed defensive assignment or three. For every long-range shot, a bad turnover or an untimely error. But that was understandable for a young player — he’s still just 19 years old — who hadn’t really played in any organized basketball games since his appearance at the Nike Peach Jam in the summer of 2021.

As the NBA season has progressed, so has Sharpe, and he’s done it playing against the best players in the world, leaving those who have watched him to wonder what kind of impact he could have made playing against the type of lesser competition Kentucky faced during its disappointing 2022-23 campaign.

Sharpe had 12 points in just 16 minutes in his NBA debut in October and put together 10 double-digit scoring games by the end of November before hitting some rookie bumps in the road.

A disappointing season in Portland and a series of injuries to key Blazers has led to an increased opportunity for Sharpe in recent weeks, and he’s starting to make a major splash in his new role.

Going into Monday’s late-night matchup with the Pelicans, the Canada native was on a run of three consecutive games with at least 24 points. That stretch included a career-high 40 minutes in a win over the Jazz last week and a career-high 29 points — while taking just 13 shots — in a game against the Thunder on Sunday night.

For the month of March, he’s averaging 11.7 points per game while shooting 51.4 percent from the floor and 43.4 percent from three-point range.

“It has been a tough game for him to learn, you know?” Blazers Coach Chauncey Billups said earlier this month. “He really never even had a chance to learn the college game. He was thrust into learning the NBA game, and it’s a lot. It’s a lot of things to study and a lot of things to watch, but he is taking that task very seriously. He is starting now to understand what we want as a team, what his role is and what we need from him every single night.”

Billups said over the weekend that — with several starters out — he plans to deploy Sharpe against the opposing team’s best offensive player moving forward. On Friday night against the Bulls, it meant defending Zach LaVine. On Sunday night, Shai Gilgeous-Alexander was Sharpe’s assignment. Both are NBA All-Stars.

“He needs to see what it’s like in the fire,” Billups said after the Bulls game. “… I thought it was good to challenge Shaedon with those tough matchups. I’ll continue to do that, because it’s the only way he can really learn.”

While that will mean some initial struggles for Sharpe, it does speak to the Blazers’ long-term belief in him as a defender.

“Shaedon is really strong,” Billups said Sunday night. “So, he’s able to play defense without using his hands … But he actually has the type of physique that allows him to play defense with his chest a lot of times and body guys up.”

It’s obviously impossible to know what would have happened if Sharpe had come back to Lexington to play out the 2022-23 season. For one, Calipari might not have felt the need to add Reeves, who became a key part of whatever success the Wildcats enjoyed.

But there’s a good chance that Sharpe would have gone a long way toward making Kentucky’s often-stagnant offense — highly ranked as it might have been — a more dynamic one with his NBA-level ability to create for himself from the perimeter, something this UK team was lacking. And his potential on defense could have been a difference-maker by the end of the season for a Wildcats’ squad that was often woefully bad at guarding the perimeter and the rim (and poorly-rated on that end of the court, as a result).

If Sharpe had been on the court for some of those close losses over the course of Kentucky’s season, the Wildcats’ record likely would have been different. If he had been there — with a full year of college under his belt — for March Madness, perhaps the Cats might even still be playing.

“You needed one more guy …” went Calipari’s lament on the final day of UK’s season.

It’ll be a what-if that sticks with this program for a while.

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