The fourth season of *Tulsa King* premiered on Paramount+ on October 16, 2026, and the episode titled "W.W.D.D." wasted no time detonating the series' status quo.

According to TV Insider's report via AOL, the season opened with Dwight Manfredi (Sylvester Stallone) and his crew preparing a big payday as distribution for the Fifty was set to begin, with Dwight sending Quiet Ray (James Russo) a piece of the pie to keep the New York mafioso at bay.

Then the plane carrying both Cal Thresher (Neal McDonough) and Margaret Devereaux (Dana Delany) went down somewhere over the Pacific during a work trip, killing two of the show's most beloved series regulars at once.

Returning showrunner Terence Winter told TV Insider at the New York premiere that the deaths were a deliberate dramatic swing.

"We wanted to put Dwight in the most vulnerable position he could be in, not just from a danger standpoint, but from an emotional standpoint," Winter explained, adding that losing somebody he deeply cares about in tragic circumstances "totally breaks him down emotionally. He has to rebuild himself."

AOL notes Winter also reflected on how far Dwight has drifted since Season 3 ended with him murdering two people in brutal fashion, arguing the character still keeps a moral compass and integrity despite the ugly nature of the business he is in.

The double death is especially jarring because of where both characters stood. Cosmopolitan's coverage of the premiere notes Dwight is trying to finally live the straight life this season, but that things don't go smoothly for long.

As AOL points out, Cal had just been named governor of Oklahoma, and Margaret had just gotten her ranch back as a result of her help getting him elected, so cutting both stories short in one accident is a huge shock for viewers who watched those arcs build across multiple seasons.

The season runs ten episodes on Paramount+, with new installments dropping every Friday at 3 a.m. ET/12 a.m.

PT until the finale on December 18, 2026, according to Cosmopolitan's release schedule. Only episode 1's title is confirmed — "W.W.D.D." — with the remaining nine episodes listed as TBA through the December finale.

With Dwight emotionally shattered and stripped of two key figures in his life, the remaining weeks will presumably chart the rebuild Winter described.