I USE AI. For that matter, AI and I have become quite friendly. Some might even call us buddies.
For the last year or so, I’ve been working with a firm that helps train AI. (Due to an ironclad NDA, I can’t offer up details.) Admittedly, it’s an off-center situation; some of my family, friends, and colleagues point out — constantly — that I’m setting up AI to steal my own job.
That’s bullshit, of course. If you can write — and I like to think I’m pretty okay at slapping together a sentence or two — you’ll be fine.
All of which is why I’m comfortable incorporating AI into my process…but only to help out with spelling, grammar, facts, and figures. I have too much pride to let it touch my prose.
I also leverage AI for most of my Substack hero photos, because I can’t find a graphic designer who’ll fit into my budget, that budget being $0.00.
I also turn to it when the Chicago sports landscape is particularly snoozy. Like today.
Hear me out.
With the NBA Draft still a couple of weeks away, and the NFL’s OTAs wrapped up, and the MLB regular season being the MLB regular season (zzzzzzz), I decided to bring in ChatGPT and Claude to hook a brother up with some interesting hoops draft content, using the following prompt:
Create an 2026 NBA mock draft.
Use only the first 15 teams in the draft.
Each of the 15 teams will make a trade before their draft pick.
The trade could include players, present draft picks, future draft picks, or all of the above.
Each trade must work under the salary cap.
Include two or three sentences of analysis for each transaction and the subsequent draft pick.
Format as below
TEAM NAME
Team Trades
Team Receivers
Team Drafts
Analysis
Do not include what’s on the right side of the bullet point, i.e., the result shouldn’t read “TEAM NAME: Chicago Bulls,” but rather just, “Chicago Bulls.” Use the same approach for each bullet point.
This is for a Substack page, so format it for easy and attractive copying and pasting.
The below results are exactly what the models delivered, everything from the formatting and grammar, to the trade suggestions and subsequent draft picks.
Spoiler alert: Despite the fact I gave GPT and Claude a solid, detailed prompt — a skillset I honed during the above-mentioned consulting gig — it didn’t end well.
Washington Wizards
Wizards Trade
• Jordan Poole
• 2028 second-round pick
Wizards Receive
• Gary Harris (expiring)
• 2029 second-round pick
Wizards Draft
• AJ Dybantsa | SF | BYU
Analysis
Washington finally turns the page on the Jordan Poole experiment while creating additional financial flexibility. The move costs very little and clears developmental runway for a younger backcourt.
Dybantsa is widely viewed as a franchise-level talent. The Wizards get the kind of foundational wing every rebuilding team spends years trying to find.
Utah Jazz
Jazz Trade
• Collin Sexton
Jazz Receive
• Nikola Jović
• 2028 first-round pick (top-10 protected)
Jazz Draft
• Darryn Peterson | PG | Kansas
Analysis
Utah continues accumulating long-term assets while moving a veteran guard who no longer aligns with the team’s timeline. Jović provides another intriguing developmental piece.
Peterson gives the Jazz a potential lead creator capable of organizing the offense for the next decade. His fit alongside Utah’s young frontcourt is obvious.
Memphis Grizzlies
Grizzlies Trade
• Desmond Bane
Grizzlies Receive
• Jabari Smith Jr.
• 2028 first-round pick
Grizzlies Draft
• Cameron Boozer | PF | Duke
Analysis
Memphis shocks the league by cashing in one of its most valuable veterans. The Grizzlies gain frontcourt size, additional draft capital, and long-term flexibility.
Boozer immediately becomes one of the most important pieces in the organization’s future. His combination of skill, IQ, and production gives Memphis a new cornerstone next to Ja Morant.
Chicago Bulls
Bulls Trade
• Nikola Vučević
• 2029 second-round pick
Bulls Receive
• Kevon Looney
• 2028 second-round pick
Bulls Draft
• Caleb Wilson | PF | North Carolina
Analysis
Chicago finally commits to a younger direction by moving Vučević’s contract. The return isn’t flashy, but it creates flexibility and opens frontcourt minutes.
Wilson brings elite athleticism, defensive versatility, and upside. He represents exactly the type of modern forward the Bulls have lacked for years.
Los Angeles Clippers
Clippers Trade
• Norman Powell
Clippers Receive
• Jett Howard
• 2028 first-round pick
Clippers Draft
• Darius Acuff Jr. | PG | Arkansas
Analysis
The Clippers begin preparing for life beyond their current veteran core. Howard provides developmental upside while the extra first-rounder replenishes a thin asset cupboard.
Acuff gives Los Angeles a young shot creator capable of eventually taking over primary offensive responsibilities.
Brooklyn Nets
Nets Trade
• Cam Johnson
Nets Receive
• Isaac Okoro
• 2028 first-round pick
Nets Draft
• Kingston Flemings | SG | Houston
Analysis
Brooklyn converts one of its most attractive veterans into future assets. The Nets continue building one of the league’s deepest collections of young talent.
Flemings offers scoring punch, athleticism, and long-term upside. His timeline fits perfectly with Brooklyn’s rebuild.
Sacramento Kings
Kings Trade
• DeMar DeRozan
Kings Receive
• Rui Hachimura
• 2029 first-round pick
Kings Draft
• Nate Ament | SF | Tennessee
Analysis
Sacramento decides to get younger around its remaining core pieces. The additional first-round selection provides valuable flexibility moving forward.
Ament is exactly the type of high-upside wing teams covet in today’s NBA. His ceiling makes him worth the gamble.
Charlotte Hornets
Hornets Trade
• Mark Williams
Hornets Receive
• Dyson Daniels
• 2028 first-round pick
Hornets Draft
• Karim Lopez | SF | Mexico City Capitanes
Analysis
Charlotte turns a talented but injury-prone center into multiple long-term assets. Daniels provides defensive versatility and secondary playmaking.
Lopez continues the youth movement. His size, skill, and international experience make him one of the most intriguing prospects in the class.
Dallas Mavericks
Mavericks Trade
• P.J. Washington
Mavericks Receive
• Ousmane Dieng
• 2028 first-round pick
Mavericks Draft
• Keaton Wagler | SG | Kansas
Analysis
Dallas sacrifices a win-now contributor in exchange for youth and future flexibility. The move acknowledges the need for sustainable roster building.
Wagler gives the Mavericks another perimeter scorer with significant upside. His offensive game projects well alongside Luka Dončić.
Milwaukee Bucks
Bucks Trade
• Brook Lopez (sign-and-trade)
Bucks Receive
• Day’Ron Sharpe
• 2029 first-round pick
Bucks Draft
• Labaron Philon | PG | Alabama
Analysis
Milwaukee gets younger while avoiding the risk of losing Lopez for nothing. Sharpe provides immediate frontcourt depth and energy.
Philon injects badly needed speed and playmaking into an aging roster. He could contribute much sooner than most prospects in this range.
Portland Trail Blazers
Blazers Trade
• Jerami Grant
Blazers Receive
• Ziaire Williams
• 2028 first-round pick
Blazers Draft
• Morez Johnson Jr. | C | Michigan
Analysis
Portland continues prioritizing long-term assets over short-term wins. The deal creates additional opportunities for younger players.
Johnson gives the Blazers a physical interior presence who fits their developmental timeline and defensive identity.
New Orleans Pelicans
Pelicans Trade
• CJ McCollum
Pelicans Receive
• Duncan Robinson
• 2028 first-round pick
Pelicans Draft
• Mikel Brown Jr. | PG | Louisville
Analysis
The Pelicans gain flexibility while opening more offensive responsibility for younger players. The future first-rounder is a valuable bonus.
Brown gives New Orleans a dynamic creator capable of eventually running the offense. His speed and scoring ability fill a major need.
Miami Heat
Heat Trade
• Terry Rozier
Heat Receive
• Josh Green
• 2028 second-round pick
Heat Draft
• Brayden Burries | SG | Arizona
Analysis
Miami reshapes its backcourt while adding a younger two-way contributor. The Heat continue searching for long-term perimeter answers.
Burries feels like a classic Miami selection. His competitiveness and developmental upside fit perfectly within the organization’s culture.
Atlanta Hawks
Hawks Trade
• 2028 first-round pick
• Clint Capela sign-and-trade rights
Hawks Receive
• Walker Kessler
Hawks Draft
• Hannes Steinbach | PF | Germany
Analysis
Atlanta upgrades its interior defense while maintaining roster flexibility. Kessler provides a younger and more controllable solution at center.
Steinbach adds toughness, versatility, and international polish. His game complements Atlanta’s existing core pieces.
San Antonio Spurs
Spurs Trade
• Devin Vassell
Spurs Receive
• Tari Eason
• 2028 first-round pick
Spurs Draft
• Cameron Carr | SG | Baylor
Analysis
San Antonio makes an aggressive value play by converting Vassell into multiple assets. Eason’s defensive versatility fits seamlessly alongside Victor Wembanyama.
Carr gives the Spurs another explosive athlete and perimeter scorer. His upside becomes even more intriguing playing next to one of the league’s most unique stars.
WASHINGTON WIZARDS
Washington Trades
San Antonio Receives
Washington Receives
Washington Drafts
Analysis
Washington, already rebuilding with young pieces, opts to move off the first pick in exchange for a proven wing and future capital. San Antonio, desperate for a second star alongside Wembanyama, pays a steep but justifiable price. The Spurs land their long-awaited cornerstone.
UTAH JAZZ
Utah Trades
New York Receives
Utah Receives
Utah Drafts
Analysis
New York, hungry to end their championship drought, surrenders a franchise-level asset in Bridges to jump into the top two. Utah, firmly in rebuild mode, accumulates a war chest of future capital to reshape the roster. The Jazz may have just laid the groundwork for a dynasty — on paper.
MEMPHIS GRIZZLIES
Memphis Trades
Houston Receives
Memphis Receives
Memphis Drafts
Analysis
Houston moves up from outside the lottery by offering a young, proven center and a future first — a significant price to pay, but the prospect at three is worth the premium. Memphis lands a 22-year-old All-Star caliber big who pairs naturally with their existing core. Both teams walk away feeling like winners.
SAN ANTONIO SPURS (selecting with Washington’s Pick 1)
San Antonio Trades
Washington Receives
San Antonio Drafts
Analysis
Dybantsa is the safest pick at the top of this class — a scoring wing with elite athleticism, length, and shot creation who projects as a perennial All-Star. Pairing him with Victor Wembanyama gives San Antonio one of the most frightening young frontcourts in the league. This could be the moment the Spurs dynasty reboot officially begins.
NEW YORK KNICKS (selecting with Utah’s Pick 2)
New York Trades
Utah Receives
New York Drafts
Analysis
Boozer is a versatile power forward with elite rebounding, face-up scoring, and surprising playmaking ability who slots immediately alongside Jalen Brunson. New York pays a steep price, but the Knicks have been searching for a legitimate frontcourt anchor for a decade. This is an unambiguous swing-for-the-fences moment from a franchise that finally has the assets to make it.
CHICAGO BULLS
Chicago Trades
Orlando Receives
Chicago Receives
Franz Wagner
2027 Second-Round Pick
Chicago Drafts
Analysis
Chicago, lacking a clear direction, decides a proven young wing is more valuable than a high-risk prospect at four. Orlando, building around Paolo Banchero, pays a significant but calculated price to add a third star-level talent. Wagner to Chicago gives the Bulls a legitimate face-of-the-franchise option to build around.
ORLANDO MAGIC (selecting with Chicago’s Pick 4)
Orlando Trades
Franz Wagner
2027 Second-Round Pick
Chicago Receives
Franz Wagner
2027 Second-Round Pick
Orlando Drafts
Analysis
Ament is a long, switchable wing with elite defensive instincts and a rapidly developing offensive game who complements Banchero perfectly. His ability to guard positions one through four gives Orlando the versatility to build one of the Eastern Conference’s most dynamic defensive rosters. The Magic get younger, cheaper, and more dangerous in one move.
LA CLIPPERS (Pick 5, originally via Indiana)
LA Clippers Trade
Philadelphia Receives
LA Clippers Receive
LA Clippers Draft
Analysis
The Clippers, deep in their post-Kawhi rebuild, flip a top-five pick for a proven young star and future capital — a bold move that signals they believe Maxey can anchor the next era in Los Angeles. Philadelphia, running out of runway, surrenders its best asset to draft a potential cornerstone. The clock is ticking on Philly’s window to turn this gamble into results.
PHILADELPHIA 76ERS (selecting with the Clippers’ Pick 5)
Philadelphia Trades
LA Clippers Receive
Philadelphia Drafts
Analysis
Wilson is a prototype modern point forward — elite size at the guard position, natural playmaking, and a maturing scoring arsenal that projects to All-Star potential within three years. Philadelphia finally commits to a genuine rebuild by moving their best veteran asset and installing Wilson as the face of the next chapter. It’s a painful but necessary reset.
BROOKLYN NETS
Brooklyn Trades
Denver Receives
Brooklyn Receives
Michael Porter Jr.
2027 Second-Round Pick
Brooklyn Drafts
Analysis
Denver, sensing the urgency of Nikola Jokić’s prime, moves up to add a high-ceiling wing before the market closes on this class. Brooklyn accepts a proven scorer and a future pick to accelerate their own rebuild timeline with an established piece. Porter brings shooting, length, and scoring punch that Brooklyn’s young core genuinely needs.
DENVER NUGGETS (selecting with Brooklyn’s Pick 6)
Denver Trades
Michael Porter Jr.
2027 Second-Round Pick
Brooklyn Receives
Michael Porter Jr.
2027 Second-Round Pick
Denver Drafts
Analysis
Miller measured nearly 6’11” at the combine, shot 40% from three, and projects as a rare modern big who can stretch the floor and protect the rim simultaneously — exactly the co-star Jokić needs to make another title run. Pairing an elite shooting big with the best passing center in NBA history creates a near-unsolvable offensive problem. Denver may have just extended their championship window by three years.
SACRAMENTO KINGS
Sacramento Trades
Minnesota Receives
Sacramento Receives
Sacramento Drafts
Analysis
Sacramento, stuck in the NBA purgatory of perpetual play-in contention, decides a veteran toughness upgrade is more immediately valuable than a long-term lottery prospect. Minnesota, needing frontcourt depth to push past the first round, pays a meaningful price to address a glaring roster need. Randle’s physicality and mid-range game fills a genuine hole in Sacramento’s rotation.
MINNESOTA TIMBERWOLVES (selecting with Sacramento’s Pick 7)
Minnesota Trades
Sacramento Receives
Minnesota Drafts
Analysis
Johnson is one of the most offensively refined prospects in the class — an elite shot creator with a quick first step, advanced pull-up game, and the scoring instincts to be a genuine second option alongside Anthony Edwards. Minnesota desperately needs a secondary ball handler who can create off the dribble without relying on pick-and-roll sets. This pick solves that problem immediately.
ATLANTA HAWKS (Pick 8, originally via New Orleans)
Atlanta Trades
Boston Receives
Atlanta Receives
Atlanta Drafts
Analysis
Atlanta acquires a proven two-way star to pair with Trae Young, finally giving the Hawks the complementary wing talent they have been missing for half a decade. Boston, coming off a championship but squeezed by the luxury tax, moves up to grab a high-upside prospect while transitioning out of the Brown era. Both teams are making calculated long-term bets — one on a known quantity, one on potential.
BOSTON CELTICS (selecting with Atlanta’s Pick 8)
Boston Trades
Atlanta Receives
Boston Drafts
Analysis
Murray-Boyles is a relentless two-way forward with elite defensive instincts, elite rebounding, and a developing offensive game that the Celtics’ system is perfectly designed to maximize — think Jayson Tatum’s development arc applied to a more naturally physical player. Boston has proven they can turn high-character, high-IQ prospects into stars through structure, culture, and patience. Murray-Boyles looks like exactly that kind of player.
OH MY.
On the plus side, both models got the draft order right. So there’s that.
Beyond that, yikes. For instance:
No clue where they pulled the rosters from, e.g., Nikola Vucevic is very much no longer with the Chicago Bulls, and Brook Lopez is very much no longer with the Milwaukee Bucks.
They listed some of the 2025 draftees as 2026 draftees, i.e., Collin Murray-Broyles and Tre Johnson. Last time I checked, you can’t get drafted two years in a row.
GPT neglected to mention both of the teams involved in their fake deals, which made the whole mess way difficult to read. That said, I didn’t cite the need for parallel labeling in my prompt, so I guess that’s sort of my fault. Sort of. I guess.
I did, however, ask that each trade work under the salary cap, and you can’t trade Tyrese Maxey for just picks. For that matter, you can’t trade Tyrese Maxey, period.
And, er, um, Baba Miller?
The biggest takeaway from this thought experiment for hoops fans? GMs are way smarter than AI.
The biggest takeaway for us sports scribes? Artificial intelligence is a ways away from stealing our gigs.