Bill Simmons, on a recent episode of The Bill Simmons Podcast, issued a bold claim: the Milwaukee Bucks are “terrified” that the Los Angeles Clippers are positioning themselves to pursue two-time MVP Giannis Antetokounmpo when his contract expires in the summer of 2027 (The Sport Review).
Simmons framed the Clippers’ offseason strategy as a long‑game maneuver. He explained that the team is remaining competitive in the short term while simultaneously clearing the books to maximize cap space in 2027: “If you’re the Clippers, short‑term, you can compete with a puncher’s chance. But long term, you have $20 million on the books in the summer of ’27. You just have Zubac, that’s it… I think that’s their end‑game, that summer of 2027. Short‑term? Let’s try to win. Long‑term? Giannis” (Yardbarker).
NBA insider Zach Lowe echoed Simmons’s viewpoint, noting that Clippers president Lawrence Frank isn’t subtle in how he builds teams around long‑term star targets: “Lawrence Frank does not wink subtly… They might be positioning themselves for Giannis” (SI).
According to multiple reports, the Clippers currently have only one guaranteed contract on the books in 2027: center Ivica Zubac. Other key players such as Kawhi Leonard, James Harden, Bradley Beal, and Chris Paul are on short‑term or player‑option deals—giving L.A. flexibility and minimal long‑term financial commitments (Heavy Sports).
Simmons further suggested that Bucks management is reacting to this looming threat. He pointed to Milwaukee’s incendiary offseason decisions—waiving veteran Damian Lillard and signing Myles Turner in addition to re‑signing multiple role players—as moves intended to keep Giannis engaged and hopeful in Milwaukee for the next two years, while preserving their ability to compete in the Eastern Conference (The Sport Review).
The Situation in Milwaukee
Despite turmoil and speculation surrounding Giannis’s future, he has remained in Milwaukee—for now. But the Bucks are clearly acting under pressure. Simmons argues that their transactions are less about long-term sustainability and more about maximizing the immediate window, knowing that their superstar could opt out in 2027 (The Sport Review, EssentiallySports).
With the Eastern Conference appearing more open after shifts in other teams’ fortunes, the Bucks believe that stacking veterans around Giannis gives them a short-term shot—and perhaps enough traction to show commitment and retain their star (The Sport Review).
The Clippers’ Strategy
Los Angeles, under billionaire owner Steve Ballmer, is viewed as one of the most financially aggressive franchises in the league. Simmons and Lowe see the Clippers as executing a strategic plan: stay competitive but avoid long-term financial anchors until Giannis becomes available.
The core plan: assemble a competitive roster now with short-term commitments, preserve massive cap flexibility entering 2027, and position themselves as one of the few teams with the available salary space to make Giannis a max offer—and build a contender around him promptly. That mirrors the Clippers’ successful playbook in 2019, when they pursued Kawhi Leonard and Paul George (Yardbarker).
Simmons indicated that Milwaukee’s urgency—signaled by the Myles Turner signing and re-signing multiple players—is a direct response to the Clippers’ looming financial readiness and ambition (EssentiallySports, The Sport Review, Yardbarker).
Why the Bucks Are “Terrified”
Simmons’s choice of language is revealing: calling Milwaukee “terrified” points to a fear of becoming unable to compete financially in the pivotal summer of 2027. The Bucks may dread the moment Giannis hits free agency, when rival teams—particularly the Clippers—will be able to offer more compelling situations than Milwaukee, especially if the team’s current heavy short-term investments fail to produce deep postseason success (The Sport Review).
What Happens Next?
Giannis holds a player option for the 2027–28 season, meaning he could become an unrestricted free agent at that time. How he exercises that option—and how his loyalty, team success, market preference, and potential for championships factor in—will determine whether Milwaukee’s strategy buys them enough time or merely delays the reckoning (SI, The Sport Review, Yardbarker).
The Clippers, by contrast, appear to be preparing methodically. Whether they can maintain competitiveness while waiting, and whether Giannis decides to defect or stay, remains speculative—but the strategy is clear—and frightening for the Bucks if it comes to fruition.
In summary: Bill Simmons asserts that the Bucks are genuinely fearful of the Clippers’ calculated positioning—building short-term competitiveness with a deliberate long-term void, all aimed at making a blockbuster run at Giannis in the summer of 2027. If Giannis tests free agency, L.A. might be among the few teams capable of mounting a credible offer—financially and structurally. Meanwhile, Milwaukee is scrambling to extend their window and keep their franchise cornerstone engaged, running on the fear that their rival’s blueprint could usurp them entirely.
