​The article originally appeared on NESN with the note to add NESN as a Preferred Source by clicking here. It centers on the Jaylen Brown trade and positions it as one of the most dramatic missteps in recent sports history. The Celtics sent Jaylen Brown to the Philadelphia 76ers in exchange for Paul George, two lottery picks, and two second-round picks. The news was so surprising that readers could hardly believe their eyes at first glance, and it demanded multiple reads to fully grasp that it was real.
Bleacher Report columnist Lee Escobedo weighs the Brown deal in the context of the century’s worst trades, and his assessment is decidedly unfavorable for Boston. The ranking focuses on trades deemed among the worst in sports this century, placing Brown’s move at No. 6, with only five others ranked worse. As Escobedo writes, “Trading a co-star to a random contender stings. Trading him to the rival who eliminated you—and one you’ll play four times a year—takes a special kind of front-office cockiness.” He notes that Brown himself seemed stunned by the decision. The Celtics had reportedly shopped Brown for Giannis Antetokounmpo weeks earlier, hoping for a superstar swap but ultimately giving a division rival what it needed to become more formidable. While the draft picks may eventually prove valuable, Escobedo asserts that this decision will never age well for Boston.
The piece also reflects on a Boston-centric thread within the rankings. It suggests, for instance, that the move is overshadowed by a more favorable Celtics deal, such as swapping the pick used on Markelle Fultz for the one that would become Jayson Tatum. Escobedo contends that, considering long-term consequences for both franchises, the Brown deal’s negative implications are worsening with time. The lone bright spot for the Sixers, according to the article, is that they later used the Fultz pick to obtain the pick that became Tyrese Maxey.
The list leans heavily toward Boston-oriented analysis, but it also highlights a few other trades viewed more positively by Celtics supporters. For example, the deal that sent Wes Welker from the Dolphins to the Patriots ranks No. 14 on a Miami-side view of the worst deals, while the Moss-for-Raiders-to-Patriots swap is No. 12 in Oakland’s estimation of giving up Randy Moss. At the very top, No. 3 on the list places the Nets’ blockbuster trade for Paul Pierce and Kevin Garnett, which enabled the Celtics to acquire Tatum and, ultimately, Brown.
For Celtics followers, there’s a mix of negative assessment and occasional vindication across these rankings. The piece ties together historical moves with current implications, offering a long view of how certain decisions reverberate through both teams and the league. It also signals that the conversation around Jaylen Brown’s trade will continue to provoke strong opinions as the long-term effects unfold.