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Pilgrim’s Insider Notes: NBA Draft decisions, 2020-21 roster outlook

Following an exciting 18-point comeback win over Florida to close out the regular season, Kentucky was gearing up for a trip to Nashville in hopes of taking home the program’s 32nd SEC Tournament title, followed by a deep run in the NCAA Tournament.

Instead, we are now left wondering ‘what if?’ as both tournaments have been officially canceled, effectively ending the 2019-20 college basketball season.

With Kentucky specifically, we are also now (whether we like it or not) essentially fast forwarding through to pre-draft coverage and the individual players’ decisions about entering the NBA Draft or returning to Lexington.

So what do we need to know about where the Wildcats are leaning? And of those expected to take the next step forward in their respective careers, who will serve as possible replacements?

NBA Draft

Before we get into the specific players and where they are leaning, it’s important to keep in mind the upcoming hurdles college players and NBA teams could potentially face in the coming weeks and months. Depending on how long the coronavirus spreads and continues to delay and/or shut things down, could the pre-draft schedule and timing of key specific events change? Could they be canceled?

As John Calipari noted after the decision to cancel the NCAA Tournament was announced, things are up in the air right now.

“Now, they’re going on spring break and now, they don’t want them back on campus,” Calipari told ESPN on Thursday afternoon. “Now, I’m going to have four or five guys that are putting their names in the draft and you ready? When is the draft? When is the combine? Are they going to have people, players fly in with their families and agents and work them out? Well, you’re not coming to our campus because we’re not letting you. Will there even be a draft?”

This afternoon, ESPN’s Adrian Wojnarowski added that NCAA coaches have been sent a memo telling them the NBA is accepting applications to the Undergraduate Advisory Committee, which “gives feedback to players on potential draft stock.” He also added that there is a legitimate possibility that players “may have to make decisions on entering the 2020 NBA Draft with reality that there could be no audition to audition for teams individually, or attend a combine.”

If players can’t use conference tournaments, the NCAA Tournaments, individual/team workouts, and the NBA Draft Combine to boost their stock, some fringe prospects will have no choice but to return to school. If their film doesn’t turn heads of NBA personnel, betting on themselves could be a massive risk.

One thing to also keep in mind is the competitive nature of these players and the fact that each of their postseasons have been ripped from their hands. I’m not sure how much it will affect Kentucky players specifically, but I wouldn’t be surprised in the slightest if we see some rather shocking returnees throughout the college basketball world. On a deeper level, could players on the fence use the lack of closure they received this season as a key reason to return to school for one final run? It would certainly make sense.

Now, let’s look at the individual Wildcats.


Nick Richards

After two years of battling confidence issues and struggling to stay on the floor, Nick Richards made a superstar leap in his junior season at Kentucky. Establishing himself as an anchor piece inside with elite shot-blocking, rebounding, and rim-running abilities, the 7-foot center went from undrafted prospect to potential first-rounder in a single year.

While an SEC Tournament title and deep postseason run was obviously the preference, Richards’ dominant 17-point second-half performance in an 18-point comeback victory at Florida was one heck of a way to call it a career at Kentucky, along with giving NBA scouts one great final look at him.

Richards’ time in Lexington is likely done, and it should be a decision the Big Blue Nation celebrates. The junior center has earned a potential jump to the NBA.

Confidence level: 95% leaves

Tyrese Maxey

To start the year, Tyrese Maxey was seen as a sure-fire lottery pick. To end the year, the freshman guard’s stock remains right in the same area as a lock for the NBA Draft lottery.

He struggled at times shooting the ball, but with his pure knack for scoring, elite finishing ability at the rim, strong defensive potential and length, growing confidence as a lead guard, NBA teams saw all they needed to out of Maxey in his lone year at Kentucky.

Confidence level: 95% leaves

Ashton Hagans

Unlike Richards, Ashton Hagans’ sophomore campaign didn’t have the storybook ending I’m sure he was hoping for. After a stretch of elite play that led to John Calipari referring to Hagans as the “best point guard in college basketball,” the 6-foot-3 sophomore out of Cartersville, GA hit a wall in the heart of conference play, turning the ball over at least three times in ten of his last 13 games, including five games with at least five. He also shot over 40% from the field just four times in that span.

To make matters worse, some on-court frustrations and off-court distractions led to an ugly loss at home against Tennessee on Senior Night and an absence in the regular season finale in Gainesville due to “personal reasons.”

Nevertheless, the expectation – as it has been all year – is that Hagans will opt for the NBA Draft, a decision I feel he has been mostly set on for several months now.

Confidence level: 90% leaves

On the fence

Immanuel Quickley

After a breakout campaign that led to SEC Player of the Year honors in 2019-20, Immanuel Quickley has the hardest decision to make on the entire team.

On one end, Quickley has played about as well as he can at the college level as an off-ball shooting and scoring threat at the college level. If his goal is to be a bench scorer at the next level (Lou Williams and Jamal Crawford are prime examples) there’s likely not enough room to grow to justify another year in college versus making the jump to the NBA.

On the other, Kentucky has pitched for Quickley to take over the lead point guard spot next year and groom him to play both positions in the league, allowing freshman guard Devin Askew to ease his way in and find his footing. The opportunity for Quickley, who has already established himself as a star at the college level, to be in the spotlight and carve out First-Team All-America honors for a legitimate national title contender. And he’d be doing it with a chip on his shoulder after missing out on the SEC and NCAA Tournaments this year.

It’s a pitch that definitely intrigues the star guard.

When asked about his decision on Instagram, Quickley said he was “not sure yet” what he’d do, but added that a junior year “would be scary.”

As of today, he’d likely be a solid second-round draft selection, where he would probably spend the majority of his time in the G-League next year. If he takes over the point guard position and thrives, he could solidify himself as a legitimate first-rounder with guaranteed money on the table.

John Calipari said on his call-in show that he wants Quickley to go through the draft process and take it seriously, something I completely expect him to do. At the end of the day, though, the option to return to school is a legitimate one.

As SEC play progressed, I thought the writing was on the wall for Quickley to be the star of March, with an NBA Draft announcement likely to follow. With the lack of closure, the opportunity to shine as the lead guard, and Kentucky’s absolutely loaded roster, this decision could get very interesting.

Confidence level: 55% stays

EJ Montgomery

Last offseason, EJ Montgomery tested the NBA Draft waters and very nearly kept his name in. Upon his return, I was told that no matter how the 6-foot-11 forward’s sophomore season went, he was a near-guarantee to leave.

After a slow start, Montgomery began picking up steam on both ends of the floor midway through the year and into SEC play. Like Quickley, I expected the sophomore forward to build on his late success and turn it into an impressive March. Now that a tournament spotlight is no longer on the table, along with the lack of workouts and NBA Combine, Montgomery’s numbers and film alone don’t jump off the page. The difficult decision he would have had with solid numbers throughout postseason play and/or another run of impressive workouts during the pre-draft process has become much more simple.

After Nick Richards’ jump from his sophomore to junior season, Montgomery has grown more comfortable with the idea of taking over that star role in the frontcourt, as Kyle Tucker of The Athletic has noted. And as we get closer to the draft process, I’m slowly coming around to the idea of that being a legitimate possibility.

During the John Calipari call-in show, the Kentucky head coach said Montgomery has a difficult decision to make, but knows how special he can be in year three if he decides to come back.

“Yeah, but again, he and his family need to sit down,” he said. “I would hope they get as much information as they can, and then decide. He was on a really good path to close out the year. He had a different look, he had a different approach. Some kids, Willie Cauley-Stein came up to me after two years and said “I am not mentally ready.” And he comes back and ends up being the No. 6 pick in the draft. It’s all individual decisions and environments. I told EJ, “I’m with you with whatever you do. I will fight like crazy if you put your name in the draft, be ecstatic if you come back. You’re going to have to lead more, you’ll have to do more, but we’ll be with you every step of the way.”

After being the first to tell you throughout the year I didn’t envision a scenario with Montgomery back for his junior year, I now believe the cancellation of postseason play, the pre-draft process being up in the air, and Richards’ growth as a junior will ultimately push him back to Lexington.

Confidence level: 70% stays

Likely returnees

Keion Brooks Jr.

Inconsistent for much of the regular season, Keion Brooks Jr. remained patient and ultimately blossomed to close out the year. In fact, Calipari drew up the game-winning shot attempt for Brooks to close out the regular season at Florida, showing just how much faith the coaching staff has in the 6-foot-8 forward moving forward.

The expectation around the program is that Brooks sees a significant step up as a sophomore and becomes a key piece in Kentucky’s title efforts. There was some scuttlebutt on social media and on message boards that Brooks could transfer, but that would be a major shock at this point in time.

Confidence level: 95% stays

Johnny Juzang

Midway through the year, there were rumblings around the program and back on the west coast that Johnny Juzang was strongly considering a transfer this offseason. And unlike the Brooks gossip, I genuinely felt the Juzang buzz was legit.

Now, after several much-needed hot shooting performances to close out conference play, confidence has grown for the 6-foot-6 guard in a major way, and the expectation is that he is back for another season in Lexington.

Confidence level: 90% stays

The unknown

Nate Sestina

On Friday, the NCAA officially announced all Division I student-athletes participating in spring sports would receive one more year of eligibility, with further consideration coming for winter athletes.

Not long after, Nate Sestina told Kentucky head coach John Calipari that he would return to Lexington if he was allowed the opportunity.

“If they let seniors play, I’m coming back,” Sestina said, via Calipari during his call-in show Monday evening. “I want another year of this.”

While it makes complete sense for spring athletes to be granted another year of eligibility, would the NCAA do the same for winter athletes who had already completed the entire regular season of their season years? Their decision to cancel the entire NCAA Tournament was unprecedented, so even with the logistical and financial issues this could cause, it’s not like we haven’t seen crazier news in the last week alone.

It’s certainly not likely, but it’s at least something to keep in mind, especially knowing Sestina is all for it.


When news broke over a week ago that Harvard star guard Bryce Aiken would be transferring for his final year of eligibility, there were rumblings almost immediately that Kentucky would be the likely destination if they made a strong push for him.

This week, though, the 6-foot guard originally out of Elizabeth, NJ told Evan Daniels of 247Sports that he had heard from Maryland, Marquette, Seton Hall, Michigan, Iowa State, Kansas, and Gonzaga are the schools that have reached out thus far. He added that he would “definitely love to hear from” the blue blood programs, there was no word of Kentucky at this point.

2020 five-star forward Greg Brown III is still a technically an option, but given the uncertainty with Kentucky’s roster and the upcoming draft decisions, recruiting restrictions, and the updated transfer rule, I don’t see the Wildcats as frontrunners with a decision coming in the near future. The UK coaches remain in contact and have regularly worked in silence with this recruitment in particular, but the buzz surrounding Memphis, Texas, and Auburn has been too strong. If he decided to hold off on a decision for another month or two to allow for NBA decisions, I’d feel more comfortable in UK’s position.

With the spring AAU schedule canceled and the possibility of major early summer events like the NBPA Top 100 Camp and Peach Jam being canceled, it will also be interesting to see if any 2021 prospects (Paolo Banchero and Jonathan Kuminga being the two biggest names) opt to reclassify. Will they expedite their recruiting processes and make early decisions?

If you ask John Calipari, even he has no idea how recruiting or exploring the transfer portal is going to play out in the coming weeks and months.

“Well, here’s the issue right now,” he said on his call-in radio show Monday evening. “You’ve got the transfer portal that is exploding again. You’ve got the grad transfers where, again, where does that fit in for us? If Nate comes back, that happens. If EJ comes back, that happens. Now, all of a sudden, it changes things again. What if Immanuel chose to come back? … We don’t know any of that, so I can’t tell you.”

If I were to make a prediction based on the early conversations I’ve had to start the offseason, I’d bank on Kentucky going the grad transfer route or look for regular transfers if the NCAA passes the one-time immediate transfer rule, as Calipari anticipates, if necessary. With so much up in the air now that the world of sports is essentially shut down for the next month or two, along with Kentucky feeling better about the possible returns of Quickley and Montgomery, that seems like the safe bet.

Potential 2020-21 Roster

If Quickley and Montgomery return, along with Sestina potentially being granted another of eligibility, there’s a chance Kentucky doesn’t even need to add more pieces.

If Quickley departs, Bryce Aiken (or a similar elite transfer option) steps in as a legitimate scoring option for the Wildcats, while Terrence Clarke – who the staff sees fitting as a potential Tyreke Evans/Memphis role in Lexington – moves over to share primary ball-handling duties with Devin Askew.

If Montgomery opts to make the jump, Kentucky could still push for Banchero to reclassify or explore the transfer market.

In short, there are plenty of moving parts, but if things work in the Cats’ favor this offseason, we could potentially see the most rotation-level scholarship players since the 2014-15 team.

Here are just a few potential scenarios to entertain:

Immanuel Quickley/Devin Askew

Terrence Clarke/Johnny Juzang/Dontaie Allen

BJ Boston/Cam’Ron Fletcher

Keion Brooks Jr./Nate Sestina/Lance Ware

EJ Montgomery/Isaiah Jackson


Terrence Clarke/Devin Askew

BJ Boston/[Transfer]/Dontaie Allen

Keion Brooks Jr./Johnny Juzang/Cam’Ron Fletcher

Nate Sestina/Lance Ware

EJ Montgomery/Isaiah Jackson


Devin Askew/[Transfer]

Terrence Clarke/Johnny Juzang/Dontaie Allen

BJ Boston/Cam’Ron Fletcher

Keion Brooks Jr./Lance Ware

Paolo Banchero/Isaiah Jackson

No matter how this all unfolds, the expectation is that, again, the Wildcats will be stacked next season.

Article written by Jack Pilgrim

Follow me on Twitter: @JackPilgrimKSR

10 Comments for Pilgrim’s Insider Notes: NBA Draft decisions, 2020-21 roster outlook

  1. bigblue98
    5:53 pm March 17, 2020 Permalink

    Oh my – if we get IQ, EJ, Nate, Keion, JJ back with Dontaie off injury and freshmen coming in will be special season. IQ is one of my favorite players of all time – he is one of the smartest players UK has had. Also, see him being an exceptional leader!

  2. BlueSteel
    5:58 pm March 17, 2020 Permalink

    It could be a very special team and a very special year!!

  3. humboldt24
    6:02 pm March 17, 2020 Permalink

    I think the most like is your first option without Nate:

    Immanuel Quickley/Devin Askew
    Terrence Clarke/Johnny Juzang/Dontaie Allen
    BJ Boston/Cam’Ron Fletcher
    Keion Brooks Jr./Lance Ware
    EJ Montgomery/Isaiah Jackson

    And wow, there wouldn’t be another team who could hold a candle to us talent-wise.

  4. trumpetguy
    6:56 pm March 17, 2020 Permalink

    NBA people have 30+ games of evaluation already on this year alone. If one or more should slip in the eyes of scouts/GMs, it won’t be because of no NCAA tournament this year. Wish them well regardless of their decisions.

  5. channell
    7:57 pm March 17, 2020 Permalink

    I don’t have a lot of confidence in Hagans playing next season in the NBA. He’s turnover prone, can’t make a layup. I’m not convince that he is a NBA guard yet. Spending time in the D league will probably be his home for a couple years. I hope I’m wrong but I don’t see him as a solid spot on an NBA roster. Defensive player yes, but I don’t see a lot of defense in the league. Glad I’m not making his decision for him.

  6. BIGblueFootBallGuy
    11:30 pm March 17, 2020 Permalink

    IQ at point? That’s something that I would LOVE to see. He would an amazing leader. I’m pumped for next season.

  7. CatManDo
    8:10 am March 18, 2020 Permalink

    Based on the projected roster I think we will go further in the tournament next year than we did this year.

  8. UKLugo
    8:42 am March 18, 2020 Permalink

    The one thing about Brooks is that he wants to play the 3. I dont think those minutes will be there for him next year. If he wants to play, hes going to have to accept the role at the 4. Or he may look to play 3 elsewhere.

  9. BobbyBlue
    2:28 pm March 18, 2020 Permalink

    Great post, Jack and I needed a BB fix.
    What do you think is Cals plan for Allen ?
    Saw him in high school and he can really shoot it but no idea how that translates to college BB at the highest level
    Thanks again for a needed article !