Fantasy Sports

The Pros and Cons of Trading Giannis Antetokounmpo

Alan Goldsher|
Giannis Antetokounmpo
Giannis Antetokounmpo | Trevor Ruszkowski-Imagn Images

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Milwaukee Bucks

Listen, nobody in the Milwaukee Bucks organization wants to move on from Giannis Antetokounmpo.

  • Dude led the Deer to a ring.
  • Dude won a pair of MVP awards.
  • Dude’s a good dude.

But to an extent, you can blame the Greek Freak himself for this can of worms that refuses to remain shut.

Taking the whole championship/MVP thing into account, one must wonder how or why this trade stuff is in the ozone. After all, Giannis is still playing at an MVP level, and (seemingly) with as much joy as ever.

Yeah, the Bucks have had a shaky couple of years—they’ve been eliminated from the postseason in the first round for the past three campaigns, and haven’t hit the 50-victory mark since 2022-23—but the infrastructure for a title run is more-or-less still in place..especially in a parity-centric up-for-grabs Eastern Conference.

But the heart wants what the heart wants, and if Giannis’ heart wants out of Wisconsin, should the Bucks grant him his wish?

Upon first blush, that answer is a solid no. You don’t trade generational players.

Then again, maybe you do. Hashtag Luka Doncic.

If Giannis plants his flag—if he wants to be moved, period, hard stop—and if the Milwaukee brass figures it’d be better to get a haul for him now than watch him walk when he becomes an unrestricted free agent at the end of the 2028-29 season, here are some plusses and minuses:

PRO: Crazy-Good Draft Capital For Years To Come

Any Antetokounmpo deal is going to land Milwaukee a buttload of draft picks—and high-end picks at that.

Last month, in one of the many mock Freak trades that clogged up the interwebs, I had the Bucks sending Giannis and salary filler to the Boston Celtics for Jaylen Brown, Anfernee Simons, Payton Pritchard, and three, count ‘em, three firsts.

This would give Milwaukee seven firsts between now and 2030. And look what Oklahoma City did with their stockpile of picks: Won a ring and set themselves up for a bright, bright future.

CON: The Bucks Will Be Meh While the 2025-26 Eastern Conference Is Eminently Winnable

Boston and Indiana are taking a gap year while, respectively, Jayson Tatum and Tyrese Haliburton heal up from long-term injuries. The Cleveland Cavaliers had a fantastic 2024-25 regular season, but tanked in the playoffs. The New York Knicks are in the middle of a sideline regime change. The Detroit Pistons aren’t quite over the hump. And the rest of the conference is a .500 record waiting to happen.

Considering the blah state of the East, a motivated Freak could single-handedly drag the Bucks to a conference championship.

PRO: Lowered Expectations

As per ESPN's latest depth chart, the Bucks will roll into 2025-26 with a starting lineup of Giannis, Myles Turner, Kyle Kuzma, Gary Trent Jr. and Kevin Porter Jr, backed by a thin bench of Bobby Portis, Cole Anthony, and some other guys—a roster that FanDuel Sportsbook currently gives a +5000 shot at winning a ’chip, just below the injury-hobbled Celtics (+4500) and just above the injury-hobbled Pacers (+7500).

As a fan, if Giannis Antetokounmpo is on your roster, you assume your franchise will be very much in the championship mix, but if Giannis Antetokounmpo isn’t on your roster, assumptions go out the window. Which, on a certain level, is a relief.

CON: An Irate Fan Base

Remember the fallout of the Luka Doncic trade? Remember how the post-Luka crowds at Dallas’ American Airlines Center were so mopey that the arena felt like a 20,000-person wake? Remember the calls for the head of Mavs GM Nico Harrison?

Oh. Wait. They’re still calling for GM Nico Harrison’s head.

Methinks Bucks General Manager Jon Horst would not enjoy that. Not one bit.

Pro: A Fresh Start

Sometimes a superstar/team marriage hits its ceiling, and it’s possible that Giannis has done everything he can in Milwaukee.

Look at the LeBron James/Dwayne Wade/Chris Bosh-era Miami squad. After grabbing rings in 2011-12 and 2012-13, they fell to the Spurs in the Finals in 2013-14, and that was the end of the Heatles.

So maybe the Bucks themselves should play a role in mapping out their future journey, and not let the whims of a superstar—or said superstar’s contract—determine what happens next. Let’s say Milwaukee goes that route and pulls the trigger on my theoretical trade with Boston. Their depth chart would look a little something like this:

  • PG: Peyton Pritchard, Cole Anthony
  • SG: Anernee Simons, Kevin Porter Jr.
  • SF: Jaylen Brown, Gary Trent Jr.
  • PF: Kyle Kuzma, Bobby Portis
  • C: Myles Turner, Jericho Sims

That gives them a ton of positional flexibility—essential in today’s NBA—a scary-good bench, and a ten-man rotation with an average age of 27.2-years-old…not to mention a pair of first rounders in the 2026 Draft which SB Nation calls, “A class worth tanking for.”

That puts Milwaukee in the championship conversation today, tomorrow, and well beyond.

CON: Trading Superstars Rarely Works

Since 1972, only two teams have won a ring within five years of shipping a future Hall of Famer in his prime out of town:

  • 2009: The Los Angeles Lakers took home the hardware five seasons after moving on from Shaquille O’Neal.
  • 2004: The Detroit Pistons won a ring four years after dealing Grant Hill.

Thus, history tells us that a Giannis trade could set the Bucks back for decades. But logic tells us that a stacked roster with future draft capital galore has a fine chance of laying claim to a Larry O’Brien Trophy sooner than later.

So you’ve got pros.

And you’ve got cons.

But what you mostly have are question marks.

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Alan Goldsher
ALAN GOLDSHER

Alan Goldsher has written about sports for Sports Illustrated, ESPN, Apple, Playboy, NFL.com, and NBA.com, and he’s the creator of the Chicago Sports Stuff Substack. He’s the bestselling author of 15 books, and the founder/CEO of Gold Note Records. Alan lives in Chicago, where he writes, makes music, and consumes and creates way too much Bears content. You can visit him at http://www.AlanGoldsher.com and http://x.com/AlanGoldsher.

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