More than four years after Drakeo the Ruler was fatally stabbed backstage at the Once Upon a Time in L.A. festival, the late rapper’s estate is offering its most detailed account yet of how it believes the event’s security system failed him.

A new collection of contracts, emails, security plans and deposition testimony filed in Los Angeles Superior Court portrays an artist compound protected by multiple security contractors, law enforcement agencies and layers of screening — but also by a vehicle-search procedure that one security vendor later concluded made it “virtually impossible” to prevent prohibited items from entering the site.

The evidence was submitted by attorneys for Drakeo’s estate in support of a motion seeking pretrial discovery into the financial condition of Live Nation Worldwide and its subsidiary C3 Presents, two defendants in the wrongful-death lawsuit filed by the rapper’s family. The Estate is pursuing punitive damages and must first convince the court that it has a substantial probability of proving that the companies acted with malice, oppression or conscious disregard for Drakeo’s safety.

The filing does not establish who killed Drakeo, whose real name was Darrell Caldwell, or demonstrate how the murder weapon entered the festival. But it provides substantial new support for the Estate’s broader contention that the artist area was not as secure as performers had been led to believe.

At the center of the Estate’s case is the system used to screen vehicles entering the artist compound.

According to an after-action report prepared by Event Security Consulting & Operations, or ESCO, artist vehicles displayed a parking pass and proceeded to a second checkpoint, where the outside of each vehicle was swept by a K9. Occupants then exited and walked through OPENGATE screening units before returning to their vehicles and proceeding to artist parking.

The dogs, however, never entered the vehicles or inspected bags, boxes or other objects left inside.

“Because the K9 units never went inside the vehicles and the occupants of vehicles were allowed to leave bags, boxes, etc. in their vehicles, it would be virtually impossible to prevent restricted items from being brought into the site despite completely functional OpenGate units,” the report states.

That assessment is particularly significant because it was made by an event-security contractor, not an expert retained by the Estate.

Pete Beattle, a representative for festival security consultant NPB Global, later testified that the K9 teams used at the artist entrance could not detect ordinary knives unless the weapons carried some type of explosive residue. Beattle also testified that no procedure required guards to physically search — or “thump” — the interiors of every artist vehicle.

Once a vehicle cleared that checkpoint, Beattle said, the remaining checkpoints were used to confirm credentials, not to conduct additional pat-downs, metal-detector screenings or searches.

The Estate paired that testimony with the account of Alrick Cooper III, a member of Drakeo’s group who testified that he arrived with a pocketknife stored in the armrest of a vehicle. Security did not discover the knife, Cooper said, and he retained access to it after the vehicle reached artist parking.

Cooper has not alleged that his pocketknife was used in Drakeo’s killing. His experience, however, appears to demonstrate how an ordinary bladed weapon could pass through the artist entrance undetected. Cooper also testified that he observed three people carrying bladed weapons during the confrontation that ended with Drakeo’s stabbing.

The new evidence also raises questions about whether festival officials knew which vehicles and guests were authorized to enter the artist area.

Nick Brown, the festival’s head of security and crowd safety, testified that he was not provided with a list of authorized artist vehicles or the vehicle passes that had been issued. Brown said he did not know how many vehicles or people were expected to arrive through the artist entrance and that there was no procedure for matching a displayed pass to the vehicle authorized to use it.

The initial checkpoint only determined whether a vehicle displayed a pass permitting it to proceed to the screening area, according to testimony included in the filing. Guards did not verify at that point whether the pass belonged to the vehicle or search its occupants.

Those admissions strengthen the Estate’s argument that the failure went beyond a single guard missing a concealed knife. Instead, its attorneys describe a system that lacked the information necessary to determine who and what should have been entering a supposedly controlled area.

The size of YG’s group has been another central issue in the lawsuit.

Drakeo’s original complaint alleged that YG received between 78 and 100 all-access passes, while Drakeo was limited to 15. The newly filed credential records do not clearly substantiate that allegation.

The email chain shows an initial allocation of 20 backstage/VIP guests and 20 additional VIP guests who were not supposed to receive backstage or stage access. Five artist-area names and three VIP names were later added, and one email noted that the group was “5 over.” Festival promoter Jeff Shuman responded, “Approved.”

That evidence could support the Estate’s contention that exceptions were made for YG’s group. But it does not establish that 78 to 100 people received all-access credentials.

A separate 2023 email from C3 to its attorney and NPB shows that a cancellation insurer was asking how approximately 100 people in “hoodies” entered a controlled area despite restrictions on group sizes. The insurer’s question is a potentially important investigative lead, but it is not proof that 100 unauthorized people breached security.

The Estate still must establish how many people participated in the confrontation, what credentials they possessed and how each entered the artist area.

The filing also introduces evidence that officials knew before the stabbing that some artists on the bill had conflicts with one another.

A Jan. 4, 2022, interagency debrief states that there was “knowledge that performers would not get along,” but participants had been reassured that the problems were mitigated. According to the notes, LAPD officials said more questions should have been asked and called for greater law enforcement involvement, more collaboration in vetting performers and proper security staffing in the artist area.

An entry attributed to the Los Angeles Fire Department said the first question officials had to answer after the festival was how they had failed to consider which artists were performing and whether any of them were “having issues with each other.”

The debrief also identified communication and command problems. LAPD was reportedly unclear about the division of responsibility between Live Nation and C3, while communication between the command post and the artist operation had stalled. An entry attributed to C3’s Sean Akhavan said the festival needed “one rule over festival grounds.”

Those records bolster an emerging theory that Drakeo’s death resulted from fragmented command as much as a failed search: Multiple companies and government agencies handled individual pieces of security, but no single operation successfully integrated performer intelligence, scheduling, credential control, vehicle screening and backstage deployment.

The scheduling evidence is especially noteworthy.

The Estate’s original complaint alleged that Drakeo was moved from a 7:10 p.m. performance to an 8:30 p.m. slot, putting him closer to YG’s scheduled appearance. But the newly filed scheduling records indicate that Drakeo was already set to perform at 8:30 p.m. and that it was YG who was moved — from 7:10 p.m. to 9:05 p.m.

The distinction matters, although it does not necessarily defeat the Estate’s underlying argument. Moving YG to a time shortly after Drakeo’s performance could have increased the likelihood that their groups would be backstage simultaneously.

Akhavan testified that no security personnel were consulted about the schedule change and that Shuman approved the revised timing.

The contracts included in the filing appear designed to prevent Live Nation and C3 from placing all responsibility on outside security contractors.

C3 retained Black Tide Events to manage festival operations and vendors, while budgets, staffing positions and expenditures remained subject to C3 and Live Nation’s final approval, according to the documents. C3 security director John “JT” Williams was identified as the company’s primary contact for entry screening, artist screening, emergency planning, deployments, law enforcement and K9 resources.

Williams later signed a declaration stating that he approved C3’s security contractors, participated in pre-event security discussions and observed the security measures employed at the festival. He also stated that the event’s security plan was “generally implemented in full,” apart from possible minor variations that did not reduce security operations.

That declaration cuts both ways.

Live Nation and C3 can point to it as evidence that the security plan was implemented and that Drakeo’s death resulted from an unforeseeable criminal attack despite substantial precautions. The Estate can argue that full implementation makes the evidence more troubling: If the plan was followed, then the inability to keep knives out was a defect in the approved system itself, rather than an unauthorized departure by a low-level contractor.

The Estate nevertheless faces a higher hurdle in pursuing punitive damages than it does in proving negligence. It must connect the allegedly dangerous decisions to an officer, director or managing agent of Live Nation or C3 and show that the decision-maker understood the risk and consciously disregarded it.

The current record strongly suggests that the artist-entry system was unable to reliably exclude ordinary knives. It also raises serious questions about credential control, performer threat assessments and backstage command.

What it does not yet reveal is whose knife killed Drakeo, how that weapon entered the festival or which senior company official knew before the event that the security procedures were inadequate.

Those unanswered questions may determine whether the case remains a negligence lawsuit over a tragically flawed festival security operation — or becomes something far more costly for Live Nation and C3.