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Home Court filings USA v. Keough USA v. Keough — U.S. District Court, S.D. Fla., West Palm Beach Exhibit Character Letters — USA v. Keough (Dkt. 52.1)

Court filing

Exhibit Character Letters — USA v. Keough (Dkt. 52.1)

Filed January 31, 2024 in USA v. Keough; one of 55 filings from this case.

Record facts

CourtU.S. District Court for the Southern District of Florida
Filed2024-01-31

U.S. District Court for the Southern District of Florida · No. 9:23-cr-80154-DMM · Doc. 52-1 · 2024-01-31 · Docket on CourtListener

Full text

From: "Gilbert, Charlie" <cgilbert@gdba.com> 
Date: Wednesday, November 8, 2023 at 7:59 PM 
To: "robin.waugh@usdoj.gov" <robin.waugh@usdoj.gov> 
Cc: "davidjjoffe@aol.com" <davidjjoffe@aol.com>, "patrick@mckameydefenselaw.com" 
<patrick@mckameydefenselaw.com> 
Subject: Greg Keough 
  
 Ms. Robin Waugh 
U.S. Department of Justice 
  
Dear Ms. Waugh; 
  
My name is Charlie Gilbert.  I am writing to you at the request of Greg Keough, who I understand 
has a pending legal issue before you.  I am currently employed as Director of Intelligence at Gavin 
de Becker and Associates (https://gdba.com/executives/charlie-gilbert/).  From 1990-2016 I was an 
officer in the Central Intelligence Agency. In addition to other assignments, I was a three-time Chief 
of Station and served as the Deputy Director of the National Clandestine Service. I am the recipient 
of the Distinguished Career Intelligence Medal, the Intelligence Medal of Merit, the Donovan Award, 
and other citations. 
  
I came to know Mr. Keough very early in my career at CIA, when we were classmates during the 
intensive, two-year Career Trainee training program we both successfully completed to start our 
careers.  During such an intensive course, one comes to know one’s classmates very well.  After our 
training program Mr. Keough went into operations in Latin America, while I went to the Near East, so 
we did not serve together after our two-year training.  Nonetheless, we remained in contact and 
would occasionally socialize over the years, when we found ourselves in the same place at the same 
time, and we maintain many mutual friendships to this day.  
  
I can gladly confirm that Mr. Keough was an Operations Officer with the Directorate of Operations, 
the clandestine arm of the CIA, and served his country with distinction. I can further confirm that 
while on assignment abroad Mr. Keough received the CIA’s Intelligence Star – one of the Agency’s 
highest awards for service and rarely awarded - for his actions when he went to the rescue of a 
fellow officer on July 19th, 1992.  Mr. Keough’s actions on that day were in the finest tradition of CIA 
officers’ bravery and selflessness.  I recall the message sent out to all CIA Stations citing and 
lauding Mr. Keough’s efforts on that day. 
  
While he saved an officer’s life that day,  another officer involved in the rescue perished. The details 
of that officer’s enshrinement on the CIA’s memorial wall are 
here https://www.cia.gov/legacy/headquarters/cia-memorial-wall/ and give added context for Mr. 
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Keough’s efforts. (Mr. Keough’s name is omitted from the citation, due to the fact that Mr. Keough 
was under cover at that time.)   
  
Please do not hesitate to contact me at this email address or the telephone numbers below if you 
have any questions or require any additional information. 
  
Sincerely, 
  
Charlie Gilbert 
Director Global Intelligence 
Gavin de Becker & Associates 
818.505.0177 Ext. 3242, 571-521-9331 
  
Emergencies: Email is not a reliable method for communicating emergency needs.  Senders cannot be certain every 
email has been sent by their server, nor that it has been received by the addressee, nor that it will be seen within the 
time needed or expected. If you have an emergency matter, it is always wise to make initial contact by telephone. 
  
Confidentiality: This email, like all GDBA communications, is privileged and confidential. If you are not the 
addressee or responsible for delivery of the message to the addressee, please notify us immediately, and then delete 
this email. 
  
 
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From: Don Pepper <dpepper@vdi.global> 
Sent: Wednesday, November 8, 2023 7:24 PM 
To: Waugh, Robin (USAFLS) <RWaugh@usa.doj.gov> 
Cc: davidjjoffe@aol.com; patrick@mckameydefenselaw.com; Wendy <pepperwg@yahoo.com> 
Subject: [EXTERNAL] CIA Ops Officer & Intelligence Star Recipient Greg Keough 
  
Dear Ms. Waugh 
  
My name is Don Pepper and I wanted to let you know that I served abroad with Greg Keough in the 
Directorate of Operations, the clandestine arm of the Central Intelligence Agency in the early 
1990's.  I am a 13 year CIA veteran and in my last position at CIA I was responsible for counter 
proliferation of WMD in multiple Middle East and South Asian countries. I am  currently CEO of VDI 
(https://vdi.global/).  My wife Wendy was a senior official in the United States Government for 26 
years and also served with Greg at the same U.S. Embassy. 
  
We have known Greg and his family for over 30 years and were present when he met his wife 
abroad. I was Greg's office mate and I can confirm his former employment and honorable service 
with CIA.  Greg is one of the few living recipients of the Intelligence Star due to his actions in 
rescuing a fellow officer on July 19th,1992.  
  
The other CIA officer who died in the rescue, Barry Castiglione [see link to CIA website below] is 
memorialized by one of the stars on the CIA's wall, of which there are roughly one hundred. One 
detail which I think is significant regarding this rescue is the fact that Greg, after having safely 
extracted the other officer at risk, went back into harm's way when no one else would, to recover the 
body of Barry to prevent his corpse from being lost at sea. I continue to consider Greg a loyal and 
trustworthy friend, who can always be counted on to do the right thing. 
  
You can see more information on the CIA website and online at the links below: 
Memorial Wall:  https://www.cia.gov/legacy/memorial-wall/ 
Intelligence Star:  https://en.wikipedia.org/wiki/Intelligence_Star 
Barry Castiglione (Posthumously):   https://www.cia.gov/legacy/honoring-heroes/heroes/barry-s-
castiglione/ 
  
If you would like any further information, we can be reached via my mobile phone at 1-703-932-9836 
or the emails above.  
  
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Thank you and best regards, 
  
Don and Wendy Pepper 
 
Don L. Pepper 
CEO 
 
 
 
44125 Woodridge Parkway 
Suite 200 
Leesburg, VA 20176 
703-729-2700 (w) 
703-932-9836 (c) 
www.vdi.global 
 
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20 January 2024 
The Honorable Donald M. Middlebrooks 
United States District Court Judge 
Paul G. Rogers Federal Building and U.S. Courthouse 
701 Clematis Street Room 257 
West Palm Beach, Florida 33401 
Your Honor, 
 
I write to you as someone who has known Greg Keough and considered him a friend for 
over 30 years.  We first met as classmates in a U.S. government agency training program, one 
which is highly selective and screens candidates for many characteristics including honesty, 
trustworthiness and overall character.  Such characteristics are considered essential to 
suitability for employment by this U.S. government agency, given the sensitive duties and 
responsibilities that it entrusts to its officers. 
 
Following graduation from this demanding training program, Greg and I shared an 
apartment for a year in the Washington DC area prior to deploying overseas on our first 
assignments for the U.S. government.  While Greg could have sought a comfortable 
assignment in a stable country, this would not have been in keeping with his motivation for 
serving our country.  Instead, he sought out the most challenging hazardous duty assignment 
available to him, combatting the threat of an armed communist insurgency, one in which a 
number of U.S. military and U.S. government civilians had been killed. 
 
While serving honorably on this assignment, Greg further demonstrated selfless 
courage when he saved a fellow officer from drowning.  The risk to self in this action was sadly 
demonstrated by the fact that another officer who also braved the hazardous seas to help, 
drowned in the rescue attempt.  In recognition of his heroic action, Greg was awarded one of 
the agency’s highest decorations for bravery. 
 
Over the ensuing years I have also come to know Greg as a dedicated family man, in 
both good times and bad.  When we were young bachelors I was repeatedly welcomed into his 
parents’ home and treated like a member of the family.  We were in each other’s weddings.  I 
have been welcomed into his home many times since, as his own family grew to five children.  
And I was again welcomed as a veritable member of the family when his mother passed away 
from cancer. 
 
I know little of the actions which have brought Greg before your Court, nor can I 
pinpoint when or explain why Greg strayed from the more righteous path I have previously 
known him to be on.  I feel badly for his family in particular, but I am also a believer in personal 
responsibility and accountability and I know that Greg will have to answer to your Court for any 
offenses he has committed.  More importantly, I believe Greg knows this too.  In conversation 
with me he has accepted responsibility and expressed remorse for his actions that have 
brought him to this point.  He has spoken painfully of letting down those dearest to him, but 
also with a firm determination to spend his remaining years of life making it up to them.  I think 
that returning to his family, as soon as your Court and the law will allow, is his highest priority.  
And in the wake of this searing experience, I cannot imagine that he would ever violate the law 
again. 
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Jonathan B. Keough 
4115 33rd Rd. N. 
Arlington, VA 22207 
 
January 23, 2024 
 
The Honorable Donald M. Middlebrooks   
United States District Court Judge  
Paul G. Rogers Federal Building and U.S. Courthouse  
701 Clematis Street Room 257.   
West Palm Beach, Florida 33401  
 
Subject: Character Reference for Gregory Keough 
 
Dear Judge Middlebrooks, 
 
I am writing to provide a character reference for my brother, Gregory Keough. I have known 
Greg for fifty-two years, and our relationship goes beyond friendship – he is my brother. 
 
Greg and I, being siblings, have shared a lifetime of experiences and memories. We first 
met in the context of our family dynamics, and over the past fifty-two years, our bond has 
grown stronger through shared joys and challenges. Our familial ties have allowed me to 
witness his character in various aspects of life, reinforcing my belief in his inherent 
goodness. 
 
In addition to our personal relationship, Greg and I have been business partners in several 
business endeavors over the years. Throughout our professional collaborations, Greg has 
consistently exhibited integrity, honesty, reliability, and a strong work ethic. In these 
ventures, he never displayed any questionable behavior or actions that would raise 
concerns about his character. 
 
In terms of Greg's history and background, Greg comes from a stable family, is well 
educated, and dutifully served his country as an Operations O]icer with the Central 
Intelligence Agency – where he was awarded a medal for saving a colleague’s life.  Despite 
the recent turn of events, I have always known Greg to be a person of integrity, kindness, 
and sincerity. 
 
Greg is a compassionate individual who has consistently demonstrated a strong moral 
compass. He is known for his generosity, reliability, and dedication to his friends and 
family. Greg has been married for over twenty-nine years and is a devoted husband and 
father to five wonderful children who mean the world to him. His commitment to his family 
has been unwavering, and he actively participates in creating a loving and nurturing 
environment for his children. 
 
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Regarding the o]ense for which Greg is facing consequences, I firmly believe that it is an 
isolated incident and is certainly out of character for him. The circumstances surrounding 
the situation are not in alignment with his usual conduct.  Greg has taken proactive steps to 
address the root causes and has shown a commitment to ensuring that such a situation 
will not recur. 
 
During our conversations, Greg has expressed deep remorse and sorrow for the impact his 
actions may have had on others. I have witnessed him actively seeking forgiveness and 
making amends where possible. Additionally, he has sought professional guidance and 
counseling to address any underlying issues contributing to the situation. 
 
In conclusion, I urge the court to consider the totality of Greg's character and the steps he 
has taken to rectify the situation. I am confident that he has learned from this experience 
and will continue to contribute positively to society. 
 
Thank you for considering my perspective. If you require any further information or 
clarification, please feel free to contact me. 
 
Sincerely, 
 
Jonathan B. Keough 
703-282-9562 
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January 21, 2024 
 
Dear Judge Middlebrooks, 
My name is Tim Keough and I’m wri?ng with regard to Greg Keough’s upcoming sentencing. 
Greg is my second oldest brother (out of four of us) and I’ve obviously known him my en?re 50-
year life. I’ve had the opportunity to not only have him as a brother and close friend, but also as 
a cofounder and partner in several businesses some years ago.  My experience with Greg in 
both a personal and professional capacity gives me unique insight into his character. I could 
write many pages regarding Greg but have only highlighted a few anecdotes that I hope will 
help you gain a beMer perspec?ve of him.  
Growing up, my brothers and I were always very close. Despite our age differences, we 
definitely had, and s?ll have, a ?ght family bond that was enhanced by our shared experiences. 
Greg and I in par?cular always had a special bond. I’ve always looked up to him for as long as I 
can remember. He was hard working, crea?ve, fun and in all ways a steadfast brother. While I 
was quite young, we lived in a small town called Pound Ridge, New York, which was over an 
hour outside of New York City. From my recollec?ons and many family stories, growing up was 
not ideal in Pound Ridge, par?cularly for Greg and my eldest brother, Bill.  As the older two 
boys, they more directly felt the impacts of this situa?on than I or Jonathan.  Even so, we were 
kids and enjoyed ourselves as best we could. When I was only five or six years old, I remember 
wan?ng to join the older kids in whatever they were doing. Despite being the youngest of the 
bunch, Greg made sure I was included while also making sure to keep an eye on me. When we 
moved from New York to Potomac, Maryland, I was saddened to leave my friends and go to a 
new place. Even though Greg was going through the same thing, I remember him telling me 
how it will be exci?ng to making new friends and move somewhere new and how it was going 
to be all right. This type of support and personal advice was a common characteris?c of our 
rela?onship - he’d provide help and advice throughout my life.  
As we grew up, Greg con?nued to provide support and help for me, our family, and friends. As 
an example, before we le\ New York, my parents pushed Greg towards ac?ng and performing 
in commercials and television. I recall him having to travel alone to New York City to audi?on 
for various roles and parts a\er school on mul?ple occasions. Greg had success in ac?ng and, 
with some frequency, traveled with my mother to film commercials for brands such as Burger 
King. In addi?on to ac?ng, he also worked weekends at Rockrimmon Country club as a caddy.  
During this ?me, my father ended up out of work and seeking new employment and Greg 
provided his earnings to help support the family during this difficult period. When I really 
understood this later in life, I wondered how many of us would so easily help provide for our 
family in difficult ?mes.  
We were raised with a strong Catholic upbringing and faith. While many fall away from their 
faith as they become young adults, Greg’s faith con?nued and even grew as he got older. I 
recall many occasions when Greg was going to mass and I didn’t want to go, but he encouraged 
me to join.  I know that Greg has faced mul?ple challenging situa?ons through his life, and he 
leaned heavily on his faith to get him through these difficult periods. To this day, Greg has 
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con?nued to remain faithful and a very ac?ve Catholic, going to daily mass, suppor?ng the 
church, and frequently aiding the community. I recall speaking with Greg earlier in 2023 
discussing the financial and personal support he and his family were providing to individuals in 
need during the holidays - helping make their Christmas more joyful. Greg was always there to 
help where he could, and this help extended beyond his friends and family, to his community.  
Early in Greg’s career, he was working at the CIA and was sta?oned in El Salvador. While he was 
living in San Salvador, I was lucky enough to visit several ?mes as well as live with him one 
summer as I interned with the U.S. Department of State at the U.S. Embassy where Greg was 
sta?oned. During his service in El Salvador, Greg saved the life of a fellow officer and was 
awarded the Intelligence Star for his ac?ons. I was in aMendance during the award ceremony 
(see the aMached picture I s?ll keep in my office) and recall the day vividly.  While I will never 
forget going into the CIA headquarters and mee?ng the head of the CIA, the most impacaul 
part of the day was seeing the gra?tude of both the officer Greg had saved and the wife and 
young family of his comrade who died in the rescue aMempt and whose body Greg had gone 
back into harms way to retrieve. It was truly a powerful and emo?onal experience I’ll never 
forget. 
Greg and his wife, Ana Maria, were fortunate to meet when he was living and working in El 
Salvador. In Ana Maria, Greg found someone that not only was a fantas?c and loving person, 
but also shared his strong Catholic faith. Ana Maria’s family quickly embraced Greg and grew to 
love him as one of their own. I think the most enlightening example of his commitment to 
family and friends was when I and my family were visi?ng Greg, Ana Maria, and their family for 
Spring Break in 2023. Tragedy struck when the car ferry that was taking Ana Maria’s father, 
mother and two others was accidentally driven off the back of the ferry and the car quickly sank 
to the boMom of the lake. Upon hearing the news, Greg sprinted out of the house and quickly 
made his way to the site of the accident and proceeded to be one of the first in the water to try 
and save the occupants of the car. Unfortunately, only Ana Maria’s mother survived the 
accident, but Greg selflessly aMempted to save those in danger and even used diving equipment 
he secured to retrieve the bodies of those that died. Greg’s ac?ons in this instance and 
throughout his life demonstrate his character and his commitment to whatever it takes for 
family, friends, and community.  
There are countless other scenarios where Greg has gone above and beyond and has helped 
when the situa?on is tough, or someone is in need. When my mother was diagnosed with stage 
four pancrea?c cancer, Greg quickly stepped in taking her to appointments and moving one of 
his children to another room so that she and my father had a room at his house to stay with 
family. When she wanted to go home to her house in Maryland in her final days, Greg traveled 
with her and made sure she got home quickly and safely. Similarly, during COVID, Greg and Ana 
Maria welcomed with open arms their nephews who were stranded in the U.S. and couldn’t 
return to El Salvador. Without any asking, they immediately provided room and board for them 
for many months un?l they were able to get back to normal life.  
I have also worked with Greg and experienced his character and behavior in business seengs. 
A\er Greg le\ the CIA, he returned to the DC area. Together we started a company that was 
one of the first to connect customers with mortgage and home equity lenders online. We 
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bootstrapped this company with our sweat and built a plaaorm that was used by many lenders 
in the U.S. As we were building the company, we connected with some friends and family to 
discuss the poten?al to invest money in the company. We ended up obtaining a small 
investment from one of our friends - the only outside investor in the company. We aMempted 
to raise more money from various firms, but to no avail and ended up selling the company, for 
no profit. I know many people that, upon losing their own investment would have told their 
investors (friends or not) that they had lost all their money. Greg, however, insisted we figure 
out a way to make our friend whole. We decided to give her equity in the next firm we started 
as well as engaging her as a contractor in that enterprise, making her more than whole on her 
investment. Greg always focused on mee?ng and exceeding the expecta?ons of our customers 
and investors. I recall numerous conversa?ons where we discussed how to go above and 
beyond for customers to further enhance and ensure a long-term rela?onship. As we con?nued 
to expand the business, he con?nuously kept in mind our investors and was diligent about 
communica?ng good and bad news with them, building a solid rapport and trust with those 
that backed our company.  
When I learned of Greg’s current situa?on, I was stunned and surprised. Based upon my life-
long experience with Greg, this was truly out of character and not what I know of him. He has 
repeatedly expressed significant remorse to me, realizing that his ac?ons affected not only 
himself, but also his immediate family, friends, and community.  I know that Greg feels 
tremendous guilt and is anxious to atone for his ac?ons and move forward. Being separated 
from his family is the most difficult thing imaginable for him. On mul?ple occasions when we’ve 
spoken, he has expressed a desire to get back to normal and move forward rebuilding his life. I 
am certain that this situa?on is a one-?me blip on Greg’s otherwise exemplary record 
throughout his personal and business life.  
I am hopeful that this leMer has provided you a beMer understanding of Greg. I would be happy 
to answer any ques?ons Your Honor may have about Greg. 
 
Respecaully, 
 
 
Tim Keough 
703-615-8425 
 
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