Democratic strategist Jim Kessler said he is skeptical of a newly announced U.S. deal with Hamas that would see the group disarmed [1, 2].

The skepticism comes at a critical moment as the U.S. attempts to broker a permanent shift in the regional security landscape. If the deal fails, it could undermine diplomatic efforts to stabilize the area and heighten tensions between the involved parties.

Kessler expressed a desire for a successful outcome but questioned the reliability of the agreement. "I’m sceptical … I’d love to see a deal," Kessler said [1].

His doubts stem from the perceived nature of the organization. Kessler said Hamas is a "notoriously tricky, sneaky, oily negotiator" and noted that the group does not always follow through on its promises [1]. He argued that because past agreements between the U.S. and Hamas have not held, there is little reason to believe this specific deal will succeed [1, 2].

Kessler also linked the current situation to the communication style of Donald Trump. He suggested that a pattern exists where victories are declared prematurely. "One of the things Donald Trump is very good at is announcing victory and a deal, then a week or two later we don’t have victory or a deal," Kessler said [1].

The deal aims to remove the military capabilities of Hamas, but Kessler's assessment suggests that the group's history of negotiation makes such a milestone unlikely to be achieved permanently [1, 2].

Hamas is a notoriously tricky, sneaky, oily negotiator.

This skepticism highlights a recurring tension in Middle East diplomacy: the gap between a formal announcement of a deal and its actual implementation. By focusing on the negotiating history of Hamas and the rhetorical style of the U.S. administration, the critique suggests that the disarmament of a non-state actor is rarely a linear process and often relies on trust that has not yet been established.