TAMPA, Florida Natalie Khawam had been through a contentious divorce and had lost custody of her 4-year-old son after a bitter court battle against her ex-husband.
The judge in Washington who denied custody of the boy to Khawam last year had characterized her as a financially and emotionally troubled woman who had built many of her court arguments around false and dramatic claims of abuse.
It's not clear whether then-CIA director David Petraeus and General John Allen knew all of that eight weeks ago, when they each wrote letters to the judge supporting Khawam's appeal for custody of the boy.
Even so, the letters were unwise and inappropriate, according to military and intelligence analysts who say the expressions of support for Khawam have become symbols of questionable behavior by two of the nation's top warriors.
Khawam's twin sister, Jill Kelley, is at the center of the sex scandal that forced Petraeus, a retired Army general, to resign from the CIA and revealed what investigators called "flirtatious" emails between Allen and Kelley.
The letters from Petraeus and Allen - written as the FBI was uncovering the scandal - suggest they did not follow military and intelligence guidelines that warn senior officers to avoid linking their official work with personal activities in their civilian lives.
"I am shocked that they wrote those letters, and I am shocked that no one on their staff said to them, 'We need to find out more about these people,' " said Rosa Brooks, a law professor at Georgetown University and a former adviser to the Defense Department.
Military lawyers would have told Petraeus and Allen that "the intervention of someone of your level in a pending litigation is going to be a big deal and get you into hot water," Brooks said. "... Other people's marriages are really complicated. Just the words ‘custody battle' in court should have been enough."
Retired Colonel Chuck Allen, professor of leadership and cultural studies at the U.S. Army War College in Pennsylvania, said senior officers are told to avoid such situations because "it might look as though you are trying to impress or pull rank on somebody who really isn't under your purview. What you don't want is to imply an endorsement by the institution."
Petraeus commanded U.S. forces in Iraq and Afghanistan before retiring from the Army in 2011 to take over at the CIA; Allen is the current commander of U.S. forces in Afghanistan. Their letters gave glowing accounts of Khawam, 37, who befriended Petraeus and Allen when they served at MacDill Air Force Base in Tampa.
The base is home to the U.S. Central Command, which runs military operations in the Middle East and South Asia.
It was Kelley who set off the investigation that revealed the sex scandal when she complained to the FBI this year about harassing emails that mentioned Petraeus and Allen.
The FBI eventually determined that the emails were from Paula Broadwell, an Army reserve intelligence officer and co-author of a biography on Petraeus.
The investigation revealed that Broadwell and Petraeus, both of whom are married, had an affair and that Broadwell apparently saw Kelley as a rival.
It also found that Kelley, a married volunteer who helped plan social functions involving military officials at MacDill and community leaders in Tampa, had exchanged hundreds of emails with Allen, who also is married.
THE SISTERS' FINANCES
Petraeus and Allen have not commented on the letters. Friends say that the men were not romantically involved with Kelley or Khawam.
The sisters were a fixture at military functions at MacDill in recent years. Kelley and her husband, cancer surgeon Scott Kelley, hosted lavish parties for senior military brass at their stately residence near the base.
The appearance of wealth by the Kelleys and Khawam contrasts with court and tax records that show them to be deeply in debt.
Although it is not clear that Petraeus or Allen knew about the financial situation of the Kelleys or Khawam, analysts noted that large debt is a warning signal when the military vets anyone who will have significant access to its top leaders.
"Personal debts and legal issues, those are all huge, huge red flags for anyone seeking a security clearance," Brooks said, noting that until this week, Jill Kelley held a special "Friends of MacDill" pass that allowed her through security on the Air Force base.
According to county court documents, the Kelleys owe $2 million to a bank on a foreclosed office building in downtown Tampa. Another bank is seeking to foreclose on their mansion near MacDill, saying the couple owes $1.7 million.
The couple has been sued for more than $100,000 in outstanding credit card debt between them, court records indicate.
And a charity the couple formed in 2005, the Doctor Kelley Cancer Foundation, folded. The couple reported revenue of $157,284 and total expenses in the same amount, according to the foundation's 2007 tax return.
Khawam was a director of the charity, whose stated purpose was to "conduct research studies into efforts to discover ways to improve the quality of life of terminally ill cancer patients."
Almost half the money the charity raised went toward meals, entertainment, car expenses and legal fees, according to the 2007 tax return.
Khawam has filed for Chapter 7 bankruptcy protection, citing $3.6 million in liabilities, court records indicate.
Attorneys for Khawam and the Kelleys did not respond to telephone calls and emails seeking comment.
LETTERS OF PRAISE
The letters from Petraeus and Allen to the judge in Khawam's custody case, which appear in the court record, were submitted five months after Khawam's divorce was finalized on April 6.
She was ordered to pay child support of $982 a month to her ex-husband, Grayson Wolfe, a lawyer in Washington. He has not responded to requests for comment.
Khawam filed for bankruptcy less than a week after the divorce was final.
Allen's letter praised Khawam's "maturity, integrity and steadfast commitment to raising her child."
Petraeus wrote that he and his wife, Holly, had witnessed "a very loving relationship" between Khawam and her son, referring to when the Petraeuses hosted the Kelleys and Khawam for Christmas dinner.
Petraeus signed his letter "General U.S. Army (Rt)" and made no mention of his position at the CIA. Allen signed his letter as "General, United States Marine Corps."
Both asked District of Columbia Superior Court Judge Neal Kravitz to reconsider his custody decision in Khawam's case that he made in November 2011.
In that ruling, Kravitz issued a scathing assessment of Khawam's parenting skills.
"Ms. Khawam appears to lack any appreciation or respect for the importance of honesty and integrity in her interactions with her family, employers and others with whom she comes in contact," Kravitz wrote in his ruling.
Kravitz questioned domestic violence complaints filed by Khawam in Tampa, in which she had accused Wolfe of threatening to kill her by putting a gun to her head and threatening to take their son to the Middle East.
She reported "incidents of shaking the child; sexual abuse of her; and assaults of her and the child with shoes, hangers, boots, containers and belts," according to court documents.
"No physical, scientific or documentary evidence supports any of Ms. Khawam's allegations," Kravitz wrote.
The judge also wrote that Kelley was a "patently biased and unbelievable witness" when she testified about alleged domestic abuse by her twin sister's ex-husband.
(Writing by David Adams; Additional reporting by David Ingram and Tom Brown; Editing by David Lindsey and Xavier Briand)