The Chicago Bulls Can Land Giannis Antetokounmpo—but They 💯 Shouldn't
Do all-In superstar trades ever deliver NBA titles? Yes—but it’s rare. Very, very rare.
WE’VE SEEN 78 NBA champions, and of those 78, only three have successfully mortgaged their future in exchange for a ring:
In 2007, the Boston Celtics sent Al Jefferson, Ryan Gomes, Gerald Green, Theo Ratliff, Sebastian Telfair, and two first-round picks to the Timberwolves in exchange for Kevin Garnett. In 2008, the C’s won the franchise’s 17th title.
Eleven years later, the Toronto Raptors traded DeMar DeRozan, Jakob Poeltl, and a protected first-round pick to the Spurs for Kawhi Leonard. In his lone season up North, Leonard led the Raptors to the team’s first championship.
In 2019, the Los Angeles Lakers acquired Anthony Davis from the New Orleans Pelicans in exchange for Lonzo Ball, Josh Hart, and three first-round picks. Davis helped the Lakers bring home the franchise’s 17th-ever ring.
But for every mega-deal-centric championship, there’s a mega-deal-centric flop:
2019: The Los Angeles Clippers sent Shai Gilgeous-Alexander, Danilo Gallinari, and five first-round picks—plus two pick swaps—to the Oklahoma City Thunder in exchange for Paul George. Oops.
2021: In a three-team deal, the Brooklyn Nets landed James Harden, giving up Jarrett Allen, Caris LeVert, and multiple first-round picks. Oops.
2022: The Minnesota Timberwolves brought in Rudy Gobert, sending the Utah Jazz Malik Beasley, Patrick Beverley, Jarred Vanderbilt, Leandro Bolmaro, the rights to Walker Kessler, four first-round draft picks, and a pick swap. Oops.
All of which means that six NBA teams have cleaned house for a shot at a trophy, three of whom nailed it, and three of whom three blew it—which, if you run the numbers, tells us that mortgaging the future gives a team a 3.8% chance of NBA championship glory.
So why would a franchise sacrifice most, if not all of their quality assets just to land a future Hall of Famer—especially an era in which one-man teams rarely win ‘chips?
If you’re the 2025-26 Chicago Bulls, it’s because your franchise hasn’t been relevant in a decade.
WE HAVE video proof that Giannis Antetokounmpo is intrigued by the Chicago Bulls.
Bear in mind, the Greek Freak’s interest in the Land of Lincoln has nothing to do with the Bulls’ performance over the last several seasons—hell, even the Bulls aren’t intrigued by the Bulls’ performance over the last several seasons—but rather the franchise’s history.
Y’see, some current NBA players believe that donning the red-and-black will bring them spiritually closer to Michael Jeffrey Jordan. Thing is, this franchise hasn’t been spiritually close to Michael Jeffrey Jordan since, well, since forever.
It’s all about yesterday.
And it’s possible that Giannis loves Chicago’s NBA version of yesterday.
And it’s possible that Giannis isn’t giving lip service, but rather actually does want to decamp in the Windy City.
It’s also possible that bringing Giannis to Chicago via trade would be the dumbest move in the history of Chi-town sports.
And that’s saying something.
ANTETOKOUNMPO is a classy dude, not the kind of who’d guy go off on a public tirade about his team’s personnel moves—but word is he’s less-than-psyched about his Milwaukee Bucks’ decision to waive future Hall of Fame guard Damian Lillard, just so the team could afford to pay former Indiana Pacers not-future-Hall-of-Fame center, Myles Turner.
Giannis has a point.
Post-Lillard, the Bucks’ point guard situation, as of this writing, has Kevin Porter Jr. listed as the starter, with Vasilije Micic and AJ Green as his backups, and, spoiler alert, that ain’t exactly an elite backcourt.
Could the Bucks have made any noise out East in 2025-26 if they’d have kept Lillard and re-signed incumbent center Brook Lopez? Welp, with the Jayson Tatum-less Celtics in blow-it-up mode, and the defending Eastern Conference champion Pacers prepping for a season without hobbled superstar Tyrese Haliburton, the New York Knicks and the Cleveland Cavaliers would (basically) be the only obstacles standing in the way of Milwaukee’s first trip to the Finals since winning the Larry O’Brien in 2021.
The Bucks’ core of Giannis Antetokounmpo, Myles Turner, and Kyle Kuzma might well get it done…but only with a fully-engaged superstar. And without Dame D.O.L.L.A. in the house, there’s no guarantee the former MVP will have his head, heart, and body working in tandem this coming season, so it might be time for Milwaukee GM Jon Horst to reboot.
This is where the Chicago Bulls come it.
HERE’S HOW Horst can accommodate Antetokounmpo’s (theoretical) wish to spend the rest of his career in a Chicago Bulls uni:
Chicago Bulls receive
Giannis Antetokounmpo
Milwaukee Bucks receive
Matas Buzelis
Josh Giddey (sign-and-trade)
Coby White
Patrick Williams
Chicago’s 2026 first-round draft pick (top-four protected)
Chicago’s 2027 first-round draft pick (unprotected)
Chicago’s 2029 first-round draft pick (unprotected)
(Note: A third team may need to be involved for the money to work.)
That’s certainly a solid haul for Milwaukee:
In Buzelis, they land a young buck (pun intended) who teammate Ayo Dousunmu likens to Giannis himself.
In White, they land a gunner who could send Porter to the bench (where he belongs, TBH).
And in the pile of first-round draft picks, they land, well, a pile of first-round draft picks.
Not a bad way to kick off the post-Freak era.
As for the Bulls, yeah, this would all but gut their roster and kill their future draft situation, but Giannis is just 30 and shows zero sign of regression, so it’s possible—just possible—that two seasons from now, when Chicago will have shed some of their lousier contracts (we’re talking to you Nikola Vucevic, Kevin Huerter, and Zach Collins), Giannis—who’ll be at the tail-end of his prime—might be able to attract some useful free agents and help Chicago bring home their first ring since Michael Jordan’s Last Dance.
The key word there is “might.”
Because, 3.8%.