The N.R.A. Foundation describes itself as “America’s leading charitable organization in support of the shooting sports.” Each year, the foundation—which is a nonpolitical arm of the National Rifle Association, and can accept tax-deductible contributions—takes in tens of millions of dollars, mostly from small donors. Of that, it steers about twenty million dollars to the N.R.A.’s own gun-safety, training, and hunting programs. The rest goes to gun clubs and ranges, youth shooting groups, and organizations researching the Second Amendment. In a “letter of appreciation” that appeared in the foundation’s 2017 annual report, Wayne LaPierre, the executive vice-president of the N.R.A. and an ex-officio trustee of the foundation, wrote, “On behalf of the entire N.R.A. family, thank you for your dedication and for your generous contributions that keep America safe and free.”

Like all charitable groups, the N.R.A. is required to describe the amount, nature, and recipients of its grants on its annual tax filings. But, between 2013 and 2017, the N.R.A. did not disclose payments to at least one charity—a Christian organization called Youth for Tomorrow, which provides outpatient and inpatient services for children with acute psychological and behavioral problems. Founded in 1986 by the former football coach Joe Gibbs, the charity, which is based in Northern Virginia, is a favorite of conservative élites. It is not an obvious match for the N.R.A. Foundation, but the two groups do have one point of overlap: Wayne LaPierre’s wife, Susan LaPierre, is a longtime member of the Y.F.T. board and, until very recently, was its president.

Susan LaPierre joined the Y.F.T. board in 2009, and served as its president from 2013 to last December, when, according to Gary Jones, Y.F.T’s chief executive officer, she chose not to stand for reëlection. She remains “admired and respected by everyone on the board for her genuine commitment to our vulnerable children,” Jones told me. During the time of her involvement with the charity, the N.R.A. Foundation has sponsored at least seven of its events, including its annual Heart 2 Heart Gala. A formal affair held at the Ritz-Carlton in Tysons Corner, Virginia, the gala features conservative luminaries such as Taya Kyle, the widow of the Navy SEAL sniper Chris Kyle, and performances by celebrities, including the country singer Alan Jackson and the comedian Jeff Foxworthy. In 2011, the N.R.A. Foundation was described on Facebook as one of the event’s two leading sponsors. According to Y.F.T. newsletters and fund-raising brochures, the N.R.A. Foundation served as one of the gala’s top-tier sponsors on at least three more occasions: in 2013, for twenty-five thousand dollars, and in 2016 and 2017, for fifty thousand dollars each year.

This story was published in partnership with The Trace, a nonprofit news organization covering guns in America.

Y.F.T. does not reveal the identity of its donors in its tax filings, a practice that is protected by law. The N.R.A. Foundation, however, faces potential regulatory problems for not disclosing its Y.F.T. event sponsorships, according to two experts on nonprofits. The Internal Revenue Service requires charities not only to report all grants but also to note other forms of “assistance,” including “awards, prizes, contributions, non-cash assistance, cash allocations, stipends, scholarships, fellowships, research grants, and similar payments and distributions.” Philip Hackney, who worked as an attorney in the I.R.S.’s chief counsel’s office from 2006 to 2011, told me, “It’s hard to imagine why the N.R.A. wouldn’t note the sponsorships, since they seem to fall within the spirit of what’s being asked for. Choosing not to raises significant red flags.” The foundation’s support of Y.F.T. also raises concerns about whether it ran afoul of nonprofit conflict-of-interest regulations. An N.R.A. insider, such as the spouse of Wayne LaPierre, cannot benefit from a transaction for no practical reason other than a close connection to the organization. Hackney said, “The question is, Why are they not reporting the payments? Why not be open and upfront about them? Is it because the recipient is closely associated with Susan LaPierre?”

An N.R.A. spokesman said that the N.R.A. is “a proud supporter of Youth for Tomorrow.” He did not explain why the foundation did not disclose the sponsorship payments but said that they were “endorsed by the audit committee of the board of directors.” The spokesman added that the N.R.A. views its support for Y.F.T. “as an investment in our local community near our N.R.A. headquarters,” in Fairfax, Virginia, and that “the relationships forged through Youth for Tomorrow benefit the N.R.A. in many ways.”

Board members of charities are generally expected to raise money for their organization. The N.R.A. spokesman noted that Susan LaPierre “is a proud and committed volunteer for the charity, and she invites as many people as she can to join her as supporters.” In 2018, she sent an e-mail on behalf of Y.F.T., pitching recipients on serving as sponsors of the Heart 2 Heart Gala, which would include a performance by the country-music star Brad Paisley. Some of the recipients were N.R.A. venders, who provide political-consulting and fund-raising services for the organization. “I am writing today to ask you to help change a child’s life,” Susan LaPierre wrote, before providing sponsorship information. The lowest sponsorship level was seventy-five hundred dollars. “Your support makes miracles happen every day and your love is changing lives.” At least eight N.R.A. venders contributed tens of thousands of dollars, combined, to Y.F.T. Tracy and Clinton Key, who are partners in one of the venders, Key & Associates, told me that their family “has been involved with Youth for Tomorrow since its founding.” They acknowledged that “Susan has asked for help,” but said that they have “never been pressured to donate to Y.F.T. by Susan or anyone else.” Seven others did not respond to requests for comment. James Fishman, an expert on nonprofit law and a co-author of “New York Nonprofit Law and Practice: With Tax Analysis,” told me, “If Susan is looked at as an agent of her husband, then a regulator would say that this is improper. A vender doesn’t want to shoot the goose that’s showering them with golden eggs.”

The past few months have been an especially fraught time for the N.R.A., as extensive reporting on self-dealing and other forms of financial mismanagement has revealed that hundreds of millions of dollars in spending have enriched senior executives and a small group of venders and individuals close to them. In April, at the N.R.A.’s annual meeting, Oliver North, the organization’s president, tried to oust Wayne LaPierre; the effort failed, and North (who serves on Y.F.T.’s board) resigned. Hours after North’s resignation, Letitia James, the attorney general of New York State, where the N.R.A. is chartered, launched an investigation into the organization’s tax-exempt status. According to Hackney, the Foundation’s sponsorship payments to Y.F.T. will likely provide another line of inquiry for James, who will want to assess whether the transactions “were part of a repeat pattern involving the LaPierres, deliberate concealment, and violations of duty of loyalty to the N.R.A.” If so, Hackney said, “The A.G. can ask for those funds to be returned to the foundation, and potentially have Wayne LaPierre removed as an N.R.A. officer.”