MISSISSAUGA, ON, CANADA - JANUARY 10:  Cliff Alexander #22 of the Wisconsin Herd dunks against the Texas Legends during the NBA G League Showcase Game 5 on January 10, 2018 at the Hershey Centre in Mississauga, Ontario Canada. NOTE TO USER: User expressly acknowledges and agrees that, by downloading and or using this photograph, user is consenting to the terms and conditions of Getty Images License Agreement. Mandatory Copyright Notice: Copyright 2018 NBAE (Photo by Randy Belice/NBAE via Getty Images)

Whatever happened to Cliff Alexander? He's in Oshkosh, Wis., playing basketball and dreaming of the NBA

Jon Greenberg
Mar 1, 2018

OSHKOSH, Wis. — Years ago, Derrick Rose told a group of reporters the Chicago-born player he looked up to growing up was none other than Jannero Pargo.

Why Pargo?

Because he was a normal-sized kid from Englewood who made it out of the South Side. Pargo played at Robeson High School, went to Arkansas and wound up carving out a decent journeyman’s career in the NBA.

The thing is, he made it.

There is a stigma to certain sections of Chicago that is hard to shake. But there is some truth to it too.

“I tell athletes from across the country, if you can make it out of here, you can make it anywhere,” NBA agent Reggie Brown told me recently. 

Brown, a longtime agent at Chicago-based Priority Sports, was talking to me in the concourse of the United Center during halftime of a Bulls game. The subject was one of his clients, Cliff Alexander, a former high school star from the South Side whose ascent from prep star to NBA player has been dramatically altered.

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Four years ago, Alexander was ranked as the third-best high school player in the country. He was a McDonald’s All-American, a member of the US junior national select team, the Naismith prep player of the year. At his signing day ceremony, I heard two relatives counting down the months until he was a lottery pick.

It seemed like a lock. Alexander was a 6-foot-9 physical power forward with expansive shoulders and a tiny waist. A physical specimen. Raw, yes, but he had the gifts you can’t teach. Maybe he wasn’t going to be an All-Star, but he would certainly cash in on his talent. 

So, what the heck happened to Cliff Alexander?

Now 22 years old, Alexander is coming off the bench for the Wisconsin Herd of the G League, playing home games 182 miles north of Curie Metropolitan High, in Oshkosh, Wis.

The rare top high school player to go completely undrafted, he has eight games in the NBA under his belt and they came two seasons ago as a rookie with the Portland Trail Blazers.

Playing for the farm team of the Milwaukee Bucks, Alexander is averaging 16.2 points and 6.6 rebounds in 23.2 minutes per game, waiting for a call that might never come. He’s played for four different G League teams in three seasons. 

“It’s a grind,” he said after sitting out a home loss to the Ft. Wayne Mad Ants with a sprained right ankle. “I’m enjoying it, of course, but it’s definitely a grind. I’m trying to work my butt off to get back. There’s a lot of guys out there they’re looking at, a bunch of new guys coming in. So it’s pretty hard man.”

Alexander went to training camp with the New Orleans Pelicans this fall, but Brown said they didn’t have the financial flexibility to keep him at the time.

Brown tells me that “70 percent” of the teams he talks to about Alexander feel he’s an NBA player, but given the new rules for player promotion, he needs to get on a two-way contract to have a chance to go up and down.

Alexander’s story isn’t that unusual in Chicago, where high school stars earn a name and citywide reputation before getting a driver’s license. In fact, it’s kind of the norm. There are a gaggle of them who flame out after high school and become walking, talking “What if?” stories.

“I’m one of them,” Alexander said.

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He laughs. It’s an awkward moment, that admission of vulnerability.

Maybe you’re not, I offer.

“Maybe I’m not,” he said. “My NBA career hasn’t really started yet. I haven’t played significant minutes in the NBA yet. Probably never will, but…”

But…

“I hope to get 10 to 15 years in the NBA,” he said.

It’s certainly possible, but I’m sure Farragut star Ronnie Fields said the same thing when he toiled in old CBA towns like La Crosse, Wis. and Rockford, Ill. 

Four years ago, Cliff Alexander was on top of the world.

On Feb. 21, 2014, Alexander played every minute of a four-overtime victory over Jahlil Okafor and Whitney Young in the Public League championship game at Chicago State.

He was the No. 3 ranked high school senior in the country, according to ESPN, heading to Kansas, while Okafor was No. 1 and ticketed for Duke. Maybe the next time they would meet would be in the Final Four. Then, the NBA for the next decade where they would make that long D-Rose money.

Jahlil Okafor (15) and Cliff Alexander (34) pose with Carmelo Anthony and their MVP awards after the Jordan Brand Classic at the Barclays Center in Brooklyn in 2014. (Photo by Rich Graessle/Icon SMI/Corbis via Getty Images)

“It don’t really feel like four years,” Alexander said. “It felt like yesterday. Time is just flying by so fast.”

While Okafor fouled out, Alexander finished with 20 points and 12 rebounds in the win. He beamed when he put on a cheap medal and posed for pictures with his friends. After the game, they went out to dinner and watched themselves on the late SportsCenter.

“That was probably the best game I played in my life,” Alexander said, four years later, to the day.

After the city championship game in 2014, I asked him who was the better player now, him or Okafor?

“I’ll let you guys answer that one,” he’d said with a broad smile.

Four years later, Alexander is waiting for his NBA career to begin while Okafor’s career is on the wane, on the outer fringe of the rotation for one of the losingest teams in the NBA, the Brooklyn Nets, after getting exiled from the 76ers. Okafor, a true center, was drafted third overall in 2015, but he’s already outdated. He doesn’t quite fit in the modern NBA. 

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If Alexander shores up his shot and his defense, he could still have an NBA career, but as he said, time moves quickly.

Nearly all of the top-ranked players in ESPN’s Class of 2014 rankings are in the NBA, with a few finishing up decorated college careers.

Alexander didn’t play in the Herd game I drove up for. He warmed up, but was sidelined for the fourth straight game with a sprained right ankle. Instead, I watched Brandon Jennings shoot, pass and turn the ball over in his G League debut. When Marshall Plumlee executed a reverse dunk, Alexander was the first guy off the bench to congratulate him. 

Alexander still hasn’t played since Feb. 3. While he entertained himself with dreams of getting a call-up this season, that seems out of the question now. 

When he’s healthy, Alexander comes off the bench for the Herd for strategic reasons. His coach, 34-year-old Jordan Brady, told me it gives the second unit a scoring punch. It seems a bit silly — he’s definitely still a starter in the G League, but if he makes the NBA, it will also be as a reserve. 

Cliff Alexander plays against the Texas Legends during the NBA G League Showcase January 10, 2018 at the Hershey Centre in Mississauga, Ontario Canada. (Photo by Randy Belice/NBAE via Getty Images)

While Alexander can rebound and block shots, Brady says he needs to work on simple fundamentals like pick-and-roll defense to help his cause, along with just overall consistency. Alexander agreed with that assessment, noting that he’s working on his lateral quickness. Brown counsels his client that he only has to focus on such tasks for 15 minutes a game.

But getting Alexander focused is still a challenge, he relents. Brown is working on him, imploring him to get to practice an hour early, rather than 15 minutes. It’s a mission of sorts. As Brown says, he’s glad the family picked him to be Alexander’s agent, because he thinks he can still lead him on the right path. 

“I’m grateful they chose me,” he said.

Brown also represents Bobby Portis, who was picked by the Bulls at No. 22 overall the year Alexander went undrafted. If Alexander had Portis’ motor, his inner obsession with the game, who knows where he would be. Not Oshkosh, Wis., that’s for sure.

Alexander probably wasn’t exaggerating when he says the city championship was his best game. It was his last singular moment in the spotlight, even though technically, it never happened at all.

The night of that game, Curie’s bus to Chicago State’s campus was delayed at their southwest side high school. Someone had reported the team for some eligibility problems. Alexander wasn’t one of the students in question, and the team was finally released to play the game. But in the following days, the team was stripped of the title and all of its wins. Eleven days after the city championship game, Curie, playing short-handed, lost to DuSable in their regional semifinal. They were the No. 2 team in the country, according to some rankings.

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Alexander fouled out of that game, but had 25 points, 15 rebounds and eight blocks. When the final whistle blew, he crumpled to the ground in tears.

“I was [upset] that game,” he said four years later. “C’mon, they’re in our conference, man. We beat these guys by 50 points every time! Then they come and upset us. C’mon man. That hurt. If we didn’t have our key guys, we’re still supposed to beat those guys.”

In truth, Curie “only” beat DuSable that year by 25 and 27 points in their two meetings, but his point was made.

Technically, Curie, the top seed in its sectional, finished the season 0-26.

“Everybody saw those wins though,” Alexander said. “They know what they saw.”

Just like Louisville, I said.

“I feel they pain,” he said. “I feel you Louisville.”

I didn’t know it then as I watched a sobbing Alexander leave the court at King College Prep, but this was the beginning of a slow fade.

“Everything just went downhill,” he said. “I won’t say it went downhill, it just didn’t go as planned. As I had planned it to.”

Alexander played 28 games for Kansas the following season, averaging 7.1 points and 5.3 rebounds in 17.6 minutes per game. He was ruled ineligible because of a loan his mother took out and missed the NCAA tournament, making a jump to the NBA a necessity. But before that, he never really got going with the Jayhawks, which won a heated recruiting battle over the University of Illinois for his services.

Alexander made waves in-state by fake-grabbing the Illinois hat at his signing day press conference, before putting on the Kansas one. At the time, he said he did it on purpose, but anyone at the event could see how nervous he was before the ceremony. An Illinois-connected source was sure Alexander was going to commit to the Illini the night before the press conference.

Cliff Alexander had an uninspiring year in Kansas before declaring for the draft. (Photo by Cooper Neill/Getty Images)

Still, going to Lawrence made sense at the time, it just didn’t work out in his favor. Injuries hurt him early and he couldn’t supplant other players at his position. Maybe he wasn’t as good as everyone thought. Maybe he didn’t mature as a player.

“I think I fit in the system pretty good, it was just hard for me to get minutes,” he said. “But I don’t want to get into all that.”

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Alexander, who measured at 6-foot-8 1/2 with a 7-foot-3 1/2 wingspan at the NBA combine, then hurt his knee in an early June workout with the Lakers. That injury crippled his stock. But before that, “off the court” issues had already cooled off teams, Alexander and Brown said.

While nothing ever made the news, essentially, the way Brown explained it to me, Alexander was hanging out with the wrong crowd back in Chicago and word filtered back to NBA front offices.

“They were afraid of him,” Brown said.

Brown said Alexander wasn’t in the streets committing crimes — “Cliff doesn’t have a malicious bone in his body,” he said — but like a lot of kids from rougher upbringings, he had trouble separating himself from his environment. He was making himself “guilty by association.”

“He struggled with keeping it real,” Brown said.

In a 2015 story in SB Nation, Alexander’s high school coach Mike Oliver said he warned Alexander about learning to say no.

“When he was a nobody, I used to say ‘Cliff, when you make it, you’re going to lose 90 percent of your first contract because your heart is too big,'” Oliver told SB Nation’s Ricky O’Donnell.

Those days are over now. The Alexander I talked to was grounded, friendly, conversational and seemingly older than his 22 years. He and his longtime girlfriend Caelynn Manning-Allen (who also played basketball at Curie and Kansas) are expecting a daughter in March.

Brown said he got Alexander some guaranteed money from a deal with the Brooklyn Nets last year and Alexander is building a little nest egg for his family.

If he doesn’t get some NBA interest soon, he’ll be off to Europe, where a player with his skills can earn a solid income for a decade or more.

“As of now, yeah I’ll go over there,” he said. “For real it’s my job right now. It’s how I make my money. I’ve got to feed my family. Not making enough money being down here.”

Alexander’s left forearm is tattooed with reminders of home. He has the logos of every major Chicago team, including the Fire, and on the inside of his arm, he has a recreation of the Chicago Theater marquee. Alexander goes home often, working out at Tim Grover’s gym Attack Athletics in the summer. He recently went to the premiere of the Dwyane Wade-Chance the Rapper-funded movie about Orr High School’s team. He’s around and he’s still playing basketball.

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Alexander is still something of a cult hero among Chicago basketball fans, a high-flying, energetic dunking machine. He embodied everything we love about the city game. He was emotional, raw, hungry.

Chicago prep basketball hasn’t been producing brand names the past few years after an impressive run that gave us players like Patrick Beverley, Rose, Jabari Parker and more. Alexander vs. Okafor was an event. 

“There was more excitement,” Alexander said. “We were the top players in the country. No knock to them guys now, but we were the top players in the country.”

No longer a top player anywhere, Alexander wants you to know he’s doing OK, even if he’s playing in Oshkosh instead of Milwaukee with Parker or Brooklyn with Okafor. He hasn’t given up on his scaled-down dream of just making it back to the league.

“I’m still doing good,” he said. “I’m still on my grind. My route just changed a little bit from everybody else like Jahlil. He gets drafted, I don’t. My route changes, but my goal is still the same: to be an NBA player.”

Four years ago, this goal seemed like a formality. Now, well, it’s a dream.

“I’m just waiting for the perfect time,” Alexander said. “My time to shine.”

(Top photo: Randy Belice/NBAE via Getty Images)

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Jon Greenberg is a columnist for The Athletic based in Chicago. He was also the founding editor of The Athletic. Before that, he was a columnist for ESPN and the executive editor of Team Marketing Report. Follow Jon on Twitter @jon_greenberg