By flipping a single asset from the Rudy Gobert haul for massive future draft capital, Danny Ainge has positioned a risky gamble to become his next masterpiece.
Danny Ainge’s greatest trades have one defining characteristic:
Their full value wasn't completely visible when he made them.
That history makes the Utah Jazz's return for Walker Kessler particularly intriguing.
NBA Analysis recently ranked Ainge’s five greatest trades, placing Boston’s 2013 blockbuster with Brooklyn first. The Kevin Garnett acquisition, Rudy Gobert trade, decision to move down and select Jayson Tatum and Donovan Mitchell deal completed the list.
The Kessler transaction wasn't included as an independent entry.
Eventually ... it might deserve one.
Utah officially sent Kessler to the Los Angeles Lakers in a sign-and-trade for unprotected first-round picks in 2031 and 2033, plus the right to swap first-rounders in 2028 and 2030.
No player came back to the Jazz.
That leaves Utah waiting years before anyone can fairly determine what Ainge actually acquired.
Kessler, meanwhile, received a four-year contract worth approximately $130 million. Los Angeles made that commitment after he appeared in only five games last season before undergoing surgery to repair a torn labrum in his left shoulder.
The Lakers accepted both the financial and medical risk.
Utah received four opportunities to benefit from their future.
That doesn't automatically make the transaction one of Ainge’s best.
His 2013 trade with Brooklyn eventually helped Boston select Jaylen Brown and Tatum, the two foundational players behind its 2024 championship. Acquiring Garnett produced a title during his first season with the Celtics.
The Mitchell trade immediately delivered Lauri Markkanen before he developed into an All-Star, along with Collin Sexton, Ochai Agbaji, three unprotected first-round picks and two first-round pick swaps.
Kessler’s return currently consists entirely of possibilities.
But its relationship to the Gobert trade makes those possibilities considerably more interesting.
Kessler originally arrived in Utah as part of the massive package Minnesota surrendered for Gobert in 2022. The Jazz received Kessler, four other players, four first-round picks and a 2026 first-round pick swap.
Ainge has now converted one piece of that return into two additional unprotected first-rounders and two more swaps.
The Kessler deal could therefore become either an extension of the Gobert masterpiece or an all-time transaction on its own.
That distinction depends on what happens next.
If Utah uses one of the Lakers picks to select a franchise player, the trade will immediately acquire historical significance. If the swaps never convey and both selections land late in the first round, its current promise will look considerably less meaningful.
The timing creates legitimate upside.
Utah controls Lakers draft capital through 2033, the calendar year Kessler turns 32 and seven years after the trade. Los Angeles’ roster could look entirely different by then.
Ainge’s best trades required patience before becoming obvious.
The Kessler deal has given Utah four chances to reward it.
