The five most regrettable NBA offseason decisions: Bucks part ways with Dame, Suns let go of Beal, and Blazers splurge on Holiday

The 2025 NBA offseason has officially settled into its quiet phase, but it sure left behind a trail of decisions that will haunt some franchises for years to come. From the Bucks’ bewildering choice to waive Damian Lillard and splurge on Myles Turner, to the Suns’ baffling move of paying Bradley Beal to leave without getting a clear basketball return, and the Blazers doubling down with a pricey Jrue Holiday signing, this summer's maneuvers reflect desperation and poor foresight. As teams scramble to navigate salary caps and star loyalties, the fallout from these choices could shape the league’s landscape well beyond this season.

Why The Bucks’ Decision To Ditch Dame And Sign Turner Could Be Their Biggest Regret Of The NBA Offseason

The Milwaukee Bucks, under GM Jon Horst, have once again shaken the NBA world with their aggressive offseason moves—none more questionable than their move to waive Damian Lillard while signing Myles Turner to a lucrative deal. The gamble reeks of short-term desperation masked as forward thinking.

• The gamble on Giannis Antetokounmpo’s loyalty: Horst’s moves have often been about convincing Giannis to stay put, but giving up Lillard’s elite scoring and leadership is a steep price.
• Had to pay Lillard $113 million over five years to not play: The waive-and-stretch move puts $22.5 million in dead money on their books annually, crippling future flexibility.
• Turner’s fit but not a game-changer: While Turner suits up nicely beside Giannis defensively, he doesn’t elevate the Bucks into contender territory against top Eastern Conference teams.

Horst’s rationale boils down to maximizing Giannis’ prime, yet the Bucks look stuck in mediocrity with at best a 4-6 seed ceiling. The move might save the present but mortgaged the future hard, a rare misstep for a front office known for savvy drafting.

How The Suns Paying Bradley Beal To Leave Is A Stark Example Of A Franchise In Shambles

The Phoenix Suns’ decision to let Bradley Beal walk—and pay him $100 million across five years to do so—stands out as one of the offseason’s most baffling financial plays with almost no immediate on-court benefit.

• Major luxury tax relief: The Suns cut $175 million in tax liabilities this season alone, providing cap flexibility.
• No direct player return: The move is purely to unload salary and reposition for future roster tweaking amid a rebuild.
• Committed heavily to Devin Booker: Extended Booker for two more years at nearly $150 million, signaling a puzzling rebuild strategy with heavy salary commitment.

While the Suns may savor the tax savings, basketball-wise, they’re left wondering what to build around. Burning through draft capital and still shackling themselves to pricey stars doesn’t add up. This Beal saga encapsulates Phoenix’s offseason struggles and instability.

Pelicans’ Risky Moves Highlight How Quickly NBA Offseason Decisions Spiral Out Of Control

New Orleans might be the poster child for offseason miscalculations after trading up to draft Derik Queen and clogging their roster with expensive contracts that don’t quite fit the rebuild profile.

• Traded an unprotected 2026 first-round pick for Queen: A gamble on a late lottery big man that may backfire if the pick turns valuable.
• Acquired Jordan Poole and Saddiq Bey but added salary headaches: Poole’s contract extends beyond usual flexibility, creating long-term financial strain.
• Mismatch in roster construction: Trying to rebuild while holding costly contracts for role players makes the path forward murky.

The Pelicans’ front office seems caught between competing now and preparing for a proper rebuild—a luxury no one team can afford in today’s NBA economy without sacrifice.

Why The Blazers’ Offseason Splurge On Holiday Is Admirable Yet Questionable

Portland’s decision to sign Jrue Holiday to a three-year, $100 million deal showcases respect for a proven veteran but raises concerns about financial prudence in a franchise still finding its footing.

• Holiday’s undeniable value as a mentor and playmaker: Perfect for developing young talents like Scoot Henderson and Shaedon Sharpe.
• Costly contract commitment: Over $87 million committed to Holiday, Lillard, and Grant could hamper roster flexibility in coming years.
• Playoff hopes tempered: The Blazers may look to compete for a play-in spot, but breaking through in a stacked West remains doubtful.

Though Holiday brings championship pedigree, investor caution is warranted. Overpaying for mentorship turns into a luxury many rebuilding teams can’t afford without sacrificing competitive upside.