Cowboys Paid $2.4M Settlement to Cheerleaders Amidst Voyeurism Claims

Photo via CowdyCactus

Earlier this month, ESPN’s Don Van Natta, Jr. revealed that the Dallas Cowboys paid a $2.4 million settlement to four members of the team’s cheerleading squad in May 2016. This confidential settlement was the result of a 2015 incident in which Cowboys’ Senior Vice President for Public Relations and Communications, Richard Dalrymple, allegedly entered the cheerleaders’ locker room, and spied on them while they were undressing. Each of the women received $399,523.27 as part of the agreement.

Who is Richard Dalrymple?

Dalrymple spent 32 years as the Cowboys’ Senior Vice President of Public Relations and Communications, before his retirement on February 2 – just days after ESPN contacted attorneys involved with the settlement. A tenure of this length suggests extreme trust from owner Jerry Jones, and by all accounts, Dalrymple was one of Jones’ closest confidants. He was considered an extended member of the Jones family, as navigating the perpetual media circus that is the Dallas Cowboys naturally endeared him to Jerry.

Dalrymple developed a reputation for being the team’s “high-profile fixer” and “media gatekeeper.”[1] He was considered “the man who made the mad hatter seem sane, having to cover Jerry Jones’ tracks.”[2] In 2011, Bleacher Report described Dalrymple, saying “he has to spin the news when his boss spins out of control. He is the one jerking the steering wheel to keep the car from crashing into a telephone pole when Jerry’s brain falls asleep at the wheel, but his mouth continues to accelerate towards disaster.”[3]

Brief Overview of Claims

One of the four cheerleaders claimed that she very clearly saw and recognized Dalrymple, and that he was “standing behind a partial wall in their locker room with his iPhone extended toward them while they were changing their clothes.” Dalrymple does not deny that he entered the cheerleaders’ locker room; rather, he claims that he did so only to use the restroom, and that he did not expect the women to be in the locker room. Typically, at least two security guards stand outside of the cheerleaders’ dressing room – one or more at each of the two entrances. On the day of the incident, however, the rear entrance was left unguarded, and Dalrymple was able to unlock the door with his security key card.

Illustration via ESPN

While searching for evidence of previous misconduct by Dalrymple, the cheerleaders and their attorneys came across a Facebook post from a Cowboys fan that alleged further alarming behavior. This fan claimed to have watched Dalrymple taking “upskirt” photos of Charlotte Jones Anderson, a team Senior Vice President and Jerry Jones’s daughter, on the livestream of the Cowboys’ war room during the 2015 NFL Draft. The fan signed an affidavit attesting to this claim, and the cheerleaders’ attorneys raised this issue in a September 2015 letter to Cowboys lawyers.

The cheerleaders promptly reported the dressing room incident to a security guard, and three people claimed that the security guard wanted to contact the Arlington police department. Under Texas law, it is a felony to take a photo or video of “an intimate area of another person” without their consent, and a misdemeanor to secretly observe someone without their consent. 

Cowboys’ Response

A representative for the team said that the organization “thoroughly investigated” both of the alleged incidents, and “found no wrongdoing by Dalrymple and no evidence that he took photos or video of the women.” Communications consultant Jim Wilkinson went on to say that the Cowboys had handled the investigation “with best legal and HR practices.”[4]

Wilkinson stated that the investigation started on September 2, 2015, the same day as the incident. Jason Cohen, the team’s general counsel, confiscated Dalrymple’s work-issued cell phone and supposedly hired a forensic firm to ensure that no photos or videos had been deleted. One of the four women questioned whether the Cowboys had investigated Dalrymple’s personal cell phone, as well; Cohen replied that Dalrymple was adamant that he had only the work-issued phone. Dalrymple apparently told the organization that he did not own a personal cell phone. The security guard did not mention wanting to call the authorities in his interview.

Wilkinson said that the investigation began by taking statements from the cheerleaders. However, team officials reportedly did not meet with the cheerleaders until September 10.  At these meetings, team officials told the cheerleaders that they had interviewed Dalrymple, and repeated his stated defense – that he was simply attempting to use the restroom and did not expect the women to be in the dressing room when he entered.

The Cowboys were made aware of the “upskirt” allegation in May 2015 – a few weeks after the NFL Draft, when the incident allegedly occurred. A team source told ESPN that HR had watched the video, and that Dalrymple was absolved of any wrongdoing.

In October 2015, the Cowboys reportedly issued Dalrymple a formal written warning, although a team source was unable to provide the specifics of the warning. The Cowboys also declined to share time-stamped data from security key cards and surveillance cameras that would show the exact moments at which Dalrymple entered and left the locker room.

Dalrymple had his access to the cheerleaders’ locker room revoked, and the organization made a number of security changes to the dressing room area. Security key card access was reconfigured; new signs, cameras, and communications were added to denote when locker rooms were in use; and the cheerleaders were reminded of the various legal and HR resources available to them, including employee assistance programs and an anonymous NFL hotline.

Non-Disclosure Agreements

The key element of this settlement is the non-disclosure agreement with the four cheerleaders. These women were supposedly instructed not to go public with the incident, and to not share what had happened with any of their teammates. On May 16, 2016, the cheerleaders signed, and were officially bound by, the non-disclosure agreement. The Jones family – Jerry, his two sons, Stephen and Jerry Jr., and Charlotte Jones Anderson – and Dalrymple also signed the agreement. Dalrymple once again denied that the alleged act had occurred.

This NDA “specifically bars the cheerleaders from disclosing any ‘aspect of the incident regarding Charlotte Jones Anderson,’” referring to the war room incident. One of the few exceptions allows for the cheerleaders “to respond to subpoena by federal, state or local regulatory authorities or governmental agencies.” The agreement specifically instructs the cheerleaders and their spouses that they “may only respond with ‘No Comment’” when questioned about the voyeurism allegations.

Although NDAs are far from uncommon in the sports industry, this degree of organizational control over such severe allegations involving a high-ranking team executive is concerning, to say the least. The fact that Jerry Jones’ own daughter was an alleged victim of Dalrymple’s misconduct, and that this misconduct was effectively covered up, is downright disturbing.


Sadly, workplace sexual misconduct has been at the forefront of the NFL discussion in recent months. The now-Washington Commanders, and owner Dan Snyder, have engaged in deplorable behavior towards female employees on several occasions, a number of which involved cheerleaders, as well. This pervasive misconduct resulted in Snyder being forced to hand over control of the team’s day-to-day duties, albeit to his wife, in July 2021.[5]

As the NFL and Congress work to sort out issues in Washington, this additional example of a powerful owner and organization exerting leverage over female employees must not be overlooked. This was a confidential settlement that had remained such for almost six years. This issue was very nearly swept under the rug without negative attention being brought to the Cowboys. If not for the ESPN report, it is more likely than not that Dalrymple would still be gainfully employed by the team. The NFL declined to comment on the situation, saying that “this was a club matter.”[6] As ProFootballTalk’s Mike Florio put it, “this ‘club matter’ should have been (and still should be) league business.” The irony of Jerry Jones cleaning up the mess that his “high-profile fixer” made is not lost on anyone. The ease with which a powerful entity, such as Jerry and the Cowboys, can ostensibly make these issues disappear is often much more difficult to discern – and therein lies the continuing challenge to the NFL in enforcing appropriate conduct in its member clubs.








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