Middle Men 2009

In 2004 in Houston, Jack Harris slips away from home with several million dollars stuffed in a duffel bag, intent on paying off dangerous Russian mobsters while keeping his wife Diana Harris and their children safe. The tense prologue sets a mounting sense of risk as he navigates a world where family loyalty and criminal pressure collide.

A vivid flashback transports us to 1997 Los Angeles, where Jack lends a hand to a sick friend who runs a nightclub. There, two ambitious but strung-out collaborators, Wayne Beering and Buck Dolby, strike upon a reckless idea: to monetize adult content on the internet. Buck, a former NASA scientist, dedicates himself to a quick-learned program that lets online visitors pay to view explicit material, a breakthrough that quickly sends their profits skyrocketing. They soon enlist the help of Nikita Sokoloff, a ruthless Russian mob boss who owns a local strip club; Sokoloff agrees to take a 25% stake in the venture in exchange for access and protection.

With the money rolling in, Wayne and Buck push ahead, partying in Las Vegas while some bills slip through the cracks. Jack, who has already built up a successful LA nightclub, meets the pair and becomes a partner, even paying out a hefty sum to Jerry Haggerty to exit a troubling arrangement. Haggerty, a crooked lawyer, remains a cunning wildcard as the partnership grows, and Sokoloff’s hold tightens even as his own suspicions linger.

When Sokoloff’s nephew arrives seeking a slice of the profit, tensions escalate: the nephew’s threat to Jack’s family is met with ruthless force, and one of Jack’s bodyguards fists the boy so hard that he dies. The cover story is that the nephew ran off with the money, a tale Sokoloff doubts but accepts in exchange for a larger share—raising the partnership to a 50/50 balance, with Jack caught in the middle of a dangerous negotiation.

As the business pivots from a porn site to a full-scale online billing service, they launch a company called “24/7 billing.com” and become the so-called Middle Men for other internet-based porn providers. The rapid wealth fuels a luxe L.A. lifestyle for Jack, who drifts away from his Houston family and begins a complicated relationship with porn star Audrey Dawns.

In the shadows, Haggerty grows more resentful and schemes to seize control of the operation. He deftly manipulates the more naïve Wayne and Buck, bringing Denny Z into the fold to provide billing for a slew of child pornography sites. The illegal undertow pulls in new danger, and Audrey’s live-streamed content becomes a conduit that attracts an international terrorist network. The FBI asks Jack and Audrey to help widen the terrorist-hunting effort, a move that makes Wayne and Buck fear the partnership could unravel and lead to their exposure.

Tension peaks when Sokoloff’s men kidnap Jack’s maid’s son, convinced the child is Jack’s. Ready to pay whatever it takes, Jack gathers several million dollars and heads to meet Sokoloff, a scene that bookends the film’s opening moment. He’s told the boy will be released if he signs a contract handing his partnership share to Wayne, Buck, Sokoloff, and Haggerty. Jack signs—but backdates the document to before Denny Z’s child-pornography business entered the picture. In a brutal turn, Sokoloff shoots Haggerty dead and lets Jack go, grateful for the money he has earned but forever entangled in the web of crime.

The authorities close in as Jack’s FBI ally charges Sokoloff, Wayne, and Buck with running billing operations for child pornography. They decide to flip on Denny Z in exchange for lighter sentences, and Sokoloff flees the country, with Moscow rumored as a possible destination. In the end, Jack returns home with the maid’s son, and Diana welcomes him back into the family, their bond tempered but intact by the ordeal.

• Jack Harris is the driving force behind the business transition from adult content to online billing, and his choices propel the entire saga.

• Diana Harris remains the steady, concerned partner whose faith in her husband is tested by the perilous path he treads.

• Wayne Beering and Buck Dolby are the impulsive architects of the venture’s early profits, chasing scale and speed as their moral lines blur.

• Nikita Sokoloff stands as the shadowy force behind the financial and violent repercussions, a constant pressure point for every other player.

• Jerry Haggerty embodies the treacherous edge of the enterprise, a pivot around which loyalties and risks turn.

• Audrey Dawns becomes a complex figure in Jack’s life, linking personal desire to a broader, dangerous web.

• Denny Z appears as a catalyst for further crime, accelerating the illegal business through his operational role.

• The film’s backdrop—1990s LA, the rise of online billing, and the global reach of illegal content—frames a tense narrative about ambition, betrayal, and the costs of chasing power.