In Too Deep

In Too Deep

Year: 1999

Runtime: 95 min

Language: English

Director: Michael Rymer

DramaThrillerCrime

A gritty drama follows Dwayne Gittens, a notorious figure known as "God" in Cincinnati's criminal underworld. Undercover officer Jeffrey Cole attempts to bring him down by infiltrating Gittens' empire, aided by his girlfriend and a determined commander. As Cole delves deeper into the dangerous world of crime, he struggles with his duty and finds himself increasingly drawn to the gangster lifestyle, blurring the lines between right and wrong.

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Timeline – In Too Deep (1999)

Trace every key event in In Too Deep (1999) with our detailed, chronological timeline. Perfect for unpacking nonlinear stories, spotting hidden connections, and understanding how each scene builds toward the film’s climax. Whether you're revisiting or decoding for the first time, this timeline gives you the full picture.

1

Graduation and first undercover assignment

Jeffrey Cole graduates from the Cincinnati police academy and, on the same day, lands an undercover assignment that earns praise from his superiors. He adopts the alias J. Reid, claiming to be from Akron to blend with the drug network. He must prove he has street cred to earn a place in God’s crew. This marks the start of his dangerous double life.

Graduation day Cincinnati, Ohio
2

Goes undercover as J. Reid to join God’s crew

Cole goes undercover posing as a drug dealer under the name J. Reid from Akron, Ohio. He must prove loyalty by accompanying God on missions and earning acceptance into the crew. At one point he chases a target but deliberately misses his shots, signaling cautious loyalty while maintaining his cover. The early undercover phase tests his nerve and deception.

Soon after undercover start Akron, Ohio
3

Mission with God’s crew; an order to kill target; Cole misses

God sends Cole on a mission to kill a man, forcing him to demonstrate his resolve. Cole chases the target but intentionally misses his shots, showing restraint and keeping his cover intact. The crew suspects loyalty but also notes his unusual aim, a sign of Cole’s internal conflict. The operation cements his status inside God’s circle.

Early mission
4

Bonds with Breezy T.

During the undercover assignment, Cole grows close to Breezy T., a member of God's crew. The growing relationship helps him blend in and gain trust, but it also tightens the risks of exposure. His personal ties begin to blur the line between officer and criminal in his mind.

During undercover infiltration
5

D'Ambrosio fears the line between cop and criminal; woods retreat

Captain Preston D'Ambrosio becomes worried that Cole is losing himself to J. Reid, blurring lines between lawman and criminal. He orders a forced hiatus, sending Cole to a remote woods retreat to regain perspective. The retreat forces Cole to confront his identity and the costs of his undercover life.

Mid-undercover period Woods retreat, remote area
6

Meets Myra and starts dating

During the hiatus, Cole meets Myra, an aspiring model, through a photography class. They begin dating, and Myra’s presence pulls him toward a life outside undercover. D'Ambrosio notices the change as Cole’s priorities shift away from the operation.

During hiatus Photography class
7

Reassignment to Gittens case; higher-ups insist on continuing undercover

DA Daniel Connelly and DEA agent Rick Scott overrule the hiatus decision and insist Cole is the only undercover officer who has penetrated God’s crew as deeply as he has. Cole is reassigned to the Gittens case and returns to undercover work. Myra gradually distances herself as Cole dives back into the operation.

After hiatus
8

Gittens grows more ruthless; Cole sees the violence escalate

Cole witnesses Dwayne Gittens’s growing ruthlessness, including torture and killings of subordinates as he tightens his grip on the operation. The violence unsettles Cole and deepens his internal conflict about where he truly stands. His grip on reality begins to blur as he stays undercover longer.

During undercover operation
9

Sting plan leads to standoff; Angela Wilson intervenes

D'Ambrosio orders a sting to catch Gittens during a supplier meeting, while Connelly and Scott push the plan despite risks. Police arrive and a gunfight erupts, with Cole choosing to shield Gittens during the chaotic standoff. Detective Angela Wilson talks him down and reminds him that he is Jeffrey Cole, not J. Reid.

Sting operation
10

Trial and conviction

Gittens is read his Miranda rights and the case moves to trial. Cole testifies against Gittens, providing insider detail that helps secure the conviction. He also puts in a good word for Breezy T., aiding in reducing his sentence, as the evidence and testimony seal Gittens’s fate.

Trial phase Courthouse
11

Press conference and aftermath

Following the conviction, Connelly and Scott hold a press conference as Cole and Myra drive away. Cole switches off the car radio, recognizing that his undercover work was essential to bringing Gittens down. Myra reminds him of the costs and the purpose of his actions, highlighting the personal toll of the job.

After conviction In car; press conference location
12

Epilogue: teaching new undercover officers

In the closing scenes, Cole is shown teaching new, young officers about undercover work. He stresses the importance of keeping a firm guard on one’s cover and avoiding going too deep. The film ends with a cautionary note about the personal price of undercover life.

Epilogue Police training facility
13

The story’s real-life basis

The film is based on the true story of Darryl 'God' Whiting and Boston Housing Officer Jeff Coy. Coy’s suicide three years after the case is noted, alongside Whiting’s life sentence, grounding the events in real life. The credits acknowledge these real-world inspirations and outcomes.

End credits

Last Updated: November 22, 2025 at 15:58

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Characters, Settings & Themes in In Too Deep

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