S

The Succession Battle
For A Prison Empire

EXPOSE OF JON LOGAN CEO OF PRISON MAIL
SCANNING “SMARTCOMMUNICATIONS” !

Luxury cars, mansions, a superyacht called Convict, and wined-and-dined sheriffs
— alegal war is exposing the big business of extracting profits from prisoners.

h Katya Schwenk - March 2025

The yacht is mooted at the mouth of the Miami River, i the long shadows of the
city's luxury hotels and high-rises. It s of Italian design: sleek, imposing, witha
flybridge and sundeck and five cabins, and a price point of about $10 million. On
the hul, bold silver lettering declares its name: Convit.

The Convict is the crown jewel of prison technology company Smart
Communications, whose CEO, Jonathan Logan, has a reputation for flaunting the
millions he has made in the business of prisons and jails. There is also Logan’s
$300,000 Lamborghini, with a license plate that reads “INMATE There are the
‘photos he posts dressed in garish suits, posed in the driver’s seat of his Rolls-Royce.
The Convict s harbored in a marina in
downtown Miami.

The yachts, the cars — they all form
part of Smart Communications’
“empire;” as insiders refer to it. The
company rakes in tens of millions in
revenue each year from its prison
communications tech, a business
‘model that mostly involves charging
people incarcerated in the U, prison
system to send emails (50 cents a pop)
or make phone calls (7 cents a minute)
or leave 30-second voicemails ($1
each).

Itis an empire over which Logan is
‘now battling for control

Logan once owned the company together with his father, James Logan, who died in
2022, leaving his shares in Smart Communications to his wife. Ever since, jon
Logan has been waginga vicious fight to wrest control of the company from the
rest of his family, a succession battle that has played out in several courts across
‘multiple states, drawing yachts and mansions and a dozen exotic cars into its
crosshairs.

Inadvertently,the bitter feud has also pried open the internal workings of Smart
Communications. The result is an unparalleled look into the immense fortunes and
aggressive sales tactics driving the for-profit takeover of the nation's carceral
system.

Over thelast decade, Smart Communications has emerged as a new pioneer in the
ongoing privatization of prison services, a market that is constantly finding new
ways to squeeze pennies out of incarcerated people and their families, one of the

The $10 million yacht called Convictis a
floating metaphor for the unchecked profits of the industry.

In 2022, reporting from The Appeal revealed that Smart Communications was
offering cruises in the Caribbean to sheriffs and jal officials who bought the
‘company’s technology. At the time, Logan claimed that o such cruise had set sail.
Yetatrove of court documents now reveals how Smart Communications has —
over the course of a decade — wined and dined public officials to build its business.
Company executives brought sheriffs to steakhouses and strip clubs in an effort to
‘win contracts. They offered them all-inclusive hotel stas, spa treatments, and
'booze cruises.

Presiding over it all was Jon Logan, the company’s flashy and volatile CEO, who —
all while hosting glamorous yacht parties in Miami — has gone to great lengths to
keep the company in his own hands. His parents alleged that this included holding
them at gunpoint while demanding his father turn over his company shares.
‘The Lever’s account of Logan and Smart Communications is based on a review of
‘hundreds of pages of court documents that span nearly two decades, internal
‘company emails obtained by The Lever, and interviews with multiple former
‘company employees, including an employee who worked on the Convict. The Lever
also spoke at length with Logan, who said he was being “publicly crucified over
false information” (including the alleged gun incident) and that his legal battles are
being waged to protect the company.

“The bigger story is how peaple are willing to o this, to try and extort money from
an innocent person;” he told The Lever. “Which, ' sorry, but that is me. Pm an
innocent person. I built a business, I employ a lot of people, and I connect a lot of
families, and I've done nothing wrong. And yet 1am being painted as the bad guy”

s for the Rolls-Royce he's been photogtaphed in? Logan noted that his Phantom is
22015 model. “Guess what? I’s a 10-year-old Rolls-Royce,” he said, adding that he
'had bought it (and his $350,000 Ferrari Spider) used. “Ilike cars. There's nothing
wrong with that. I've earned that”

Jon Logan poses in his Rolls-Royce. (via

)

“A Better Mousetrap”

Charging people in prison to communicate
‘with the outside world has long been good
business. For many years, this was the domain
of prison phone companies, which began
operating payphones in the nation’s prisons
and jails 1 the 19705 It took some time,
though, before these providers began to treat
prisons as a captive market. In the beginning,
the cost of making a phone call n prison was
roughly the same as in the world beyond. By
the 19905, that had changed: Rates for prison
‘phone calls were rising dramatically, even as
telecom costs decreased for everyone else.

Perks for prison bosses have always been a central feature of this business,
although they have not always taken the form of strip clubs and Caribbean cruises.
‘As phone companies jockeyed for prison contracts in the 80s, they began to court
corrections officials by offering agencies a share of the revenue. For every $1a
prisoner spent on a phone call say, the phone company would take 60 cents, and
the prison would take the rest. Perversely, then, phone companies competed in the
prison market not by decreasing rates but by raising them.

Prison phone calls were soon stacked with surcharges and extraneous fees, revenue
that was then funneled back to prisons (the vast majority of which were taking a
cut of the profits). There was a circular logic to the growth of the industry: Mass
incarceration in the 19705 and ’80s had saddled new costs on county jails and
prisons, leaving sheriffs and corrections agencies strapped for cash. Revenue from
prison phone calls, then, was a welcome salve. And the more people who were
incarcerated, the mote phone calls would be made.

By the mid-aughts, prison telecom had become highly consolidated, with just two
firmns controlling most of the market. There was also regulation on the horizon:
The nation's telecom regulator, the Federal Communications Commission, was
‘Doised to cap prison call rates after years of pressure from reform advocates, which
‘would mean swift cuts to companies’ profits. The moment was ripe for new’
competition.

Itwas at just this moment that Trey Engelke met the Logan family. Engelke was an
insurance agent in Tampa, a magnate with deep pockets and powerful friends. His
circle included Pam Bondi, now President Donald Trump’s US. attorney general,
‘whoat the time was running for state office in Florida. A big traveling guy, and
usually had an entourage anywhere he went,”as Jim Logan would later describe
Engelke. And, critically, he was the guy who “paid for virtually everything for
everybody”

1n 2009, Engelke was dating Alexis Logan, Jon Logan's older sister, who would later
serve as Smart Communications’ attorney. (Alexis declined to be interviewed for
the story when reached by phone, and did not respond to additional inguiries) Over
dinner one night, Jim Logan told Engelke about an idea his son Jon had conceived:
Email for jails, which would be installed in payphone-like kiosks in the mess halls

“The entire concept had potential,” Engelke would later recall in a court deposition.
Phone calls and snail mail were, at that time, the only means of communication in
prisons, which had allowed telecom companies to charge sky-high rates. This, he
thought, “seemed like a better mousetrap”

An Ohio sheriffs office
demonstrates a Smart
Communications kiosk in 2015,
(via Facebook)

There was, though, the issue of
‘money. At one time, before the
family moved to Florida, jim
Logan was a business mogul in
central Michigan, where he and
his wife, Janice, had raised their
two children. He owneda
‘marina and a few different auto
businesses. But court records
indicate that, by 2009, he was in
‘ot water with the Internal
Revenue Service, and money
was tight. It was also the height
of the financial crisis — capital
was hard to come by.

Over drinks and oysters, the Logans began to court Engelke as an investor. Alexis
'had reservations about the potential business partnership, Engelke later recalled.
But he was increasingly convinced that there were millions to be made in the
Logans’ new business, Smart Communications, which had by the summer of 2010
secured a contract to provide the email technology in a small county jail in
southeastern Florida. In a few installments, Engelke put down $250,000.

‘That summer, Engelke and the Logans began what they called “prospecting”
‘meeting with different sheriffs across Florida and the South to try to sell the
technology to county jails. But business was slow: Sheriffs were skeptical about the
product. “It was hard to get other jails to want to install this; Jon Logan later
testified in court.

There was, though, something that Engelke thought could take the company
‘national: The American Correctional Association (ACA). He called it their “golden
‘goose” “The hub to the spokes, if you will, was, in my opinion, at that time the
ACA he said in a 2022 deposition.

‘The American Correctional Association, the venerable trade association for the
corrections industry, a conduit to sheriffs and prison officials across the country, an
incubator of cutting-edge prison technologies — Engelke saw the organization as
the path to big profits. And he knew the guy who led it: Mike Wade, a sheriff in
Virginia.

‘The company’s efforts to win Wade's favor became the playbook it would follow
with other targets in the years to come. An associate of Engelke’s flew Wade down
to Tampa so that the sheriff could “talk with Jim and I more about potential with
ACA, Engelke said in a deposition. The pair took the sheriff out for $100 steaks.
They brought him to a party and to the Mons Venus, a strip club in Tampa. (Wade,
‘who has since retired, did not respond to inquiries from The Lever. Engelke
declined to comment on the events)

s Engelke tells it in court pleadings, from that point forward, Wade was all in. “I
'had [Wade] telling me, I think I can make this big, and I may not run again next
term, and I may even come to you for a job;” Engelke recalled. The American
Correctional Association seemed to be behind them. The winds in the prison

technology business were shifting.

At the same time, cracks were emerging across the operation. Engelke’s
relationship with Alexis Logan was fraying; they had split by the end of 2010. He
began to understand there was deep underlying strife among the members of the
Logan family.

“{Alexis) and her brother hated each other;” Engelke said. I think Jon hated his
‘mom, too” But the only way out was forward, he thought: “I tried to, shall we say,
guide through those waters, or manage around them, s as not to sink the empire””

Engelke also began to have concerns about how corporate dollars were being spent.
Atlunch with Jon Logan early on, he recalls confronting the young executive about
a company-expensed trip to the Florida Keys.
‘They can't scam who they can't find. Let Incogni get your personal information off
the internet. Get 5% off an Incogni annual plan by using code LEVER at checkout.

“This is my fucking company;” Logan shot back, according to Engelke. “And if
want to take a girl o the Keys for the weekend and charge it to the company, Pll do
s0”

(“Did you ever investigate whether Jon Logan took this trip to the Keys using
fcompany) money?” a lawyer asked Jim Logan years later. “I didn'®," e replied)

‘There was another matter: Jon Logan was on probation fora criminal charge back
in Michigan. And it was serious.

“Viciously Cruel”

In one of his last communications to his son before his death in 2022, Jim Logan
‘wrote of his son's early “lfe of absolute indulgence” There were motorcycles,
four-wheelers, snowmobiles, and jet skis; there were personal mechanics and
personal trainers. “Your mother and I even paid someone to do your school
'homework so you could race motorcycles; he wrote.

Back then, the family lived in Lansing, Michigan. Jon Logan describes his
relationship with his mother and sister as “estranged” from a young age.

“Ever since I was a young kid, she’s kind of had this way about her he has said of
Alexis

[N Alexis Logan now works in luxury real estate.
(via Dynasty Luxury Group website)

But he was closer with his father, and as an adult
— following a stint doing professional
motoctoss — he began working with him ona
car-dealership venture. By 2007, when Logan
was 25, father and son were doing business with
another car dealer in the neighborhood, a man
named Blake Mossholder, who lived with his
wife, Amy, and their three young children.

At some point, Mossholder and the Logans got
into a dispute over money. There were
allegations of more than §75,000 being stolen;
beyond that, the details of the dispute are
‘unclear from court records. The conflict quickly
spiraled out of control. Mossholder accused Jon
Logan of chasing him in a car and took outa
restraining order against him. Then, in November 2007, series of Craigslist ads
appeared online in Lansing.

The posts were crude and clearly written by someone familiar with the
Mossholders, since they included their cellphone numbers and address. Under the
category “erotic services, they advertised sexual services provided by Mossholder’s
‘wife — “My rates are the best in town” — and requested that interested parties call
or knock on the door. Each ended the same way: *Ask for dirty amy”

At the time, Amy Mossholder was undergoing chemotherapy treatments for breast
cancer; by the time that local authorities had traced the posts to Jon Logan and
arrested him, the cancer had metastasized and spread to her lungs. She died in
2010. The Mossholders would recount in court the barrage of phone calls that came
in response to the Craigslist ads, the cars that arrived at their home. “We were in
fear,” Amy Mossholder testified at Logan's sentencing hearing in August 2008. “He
has not shown remorse for that, and I will never forget it

1n 2008, Jon Logan pleaded guilty toa charge of aggravated stalking, a felony. At his
sentencing hearing, the judge said she was “shocked beyond words at the extent of
the course of conduct and the harassment that you engaged in with this family” It
was, she said, “viciously cruel what you did to them.” She sentenced Logan to 11
‘months in county jail.

Itwas during these months in jail that Jon Logan says he developed the idea for
Smart Communications, an origin story he repeated to The Lever.

“I know the experience of being incarcerated; he said. “I know the pain that it
causes. Tknow the separation you have from your loved ones, and that's why I
created a system that has transformed this industry”

By the time he started the company in 2009, the Logans had moved to Florida, far
from Michigan and the Mossholders. The first boat Jon Logan bought with his
‘newfound riches, some years later, was a $1 million Nor-Tech. He named it Dirty
Amy. “Friends we will be taking #DirtyAmy out there and packing it full of loud
‘music and cold drinks and epic times;” Logan wrote on Facebook in June 2016, “All
aboard the #DirtyAmy”

= Jon Logan advertises a boat party on the
A abond the #DietyAmy 5 1 Diyamy in June 2016, (private post on
— e, = -acebool

Logan claims that he did not write the
Craigslist ads — “I was intentionally
i framed” he told The Lever — and
emphasized that as part of his plea deal,
the charges related to those posts were
\ ’ dropped. Yet he doesn't deny the boat's
~~ namesake. “(The Mossholders] don't
deserve sympathy he said. “I deserve
justice”

He added: “Iwant to do a tongue-in-cheek name on my boat, that’s my right. I
eamedit”
“The Trojan Horse”

In the summer of 2018, Pennsylvania prison staff began getting sick. That August,
according to state corrections officials, prison staff were sent to the emergency
xoom for potential drug exposure 48 times. Prison guards were falling il s they
processed mail and searched jail ells. In fact, they were falling ll all around the
country. The incidents fed into.2 growing hysteria about the potential dangers of
airborne exposure to fentanyl and synthetic cannabinoids.

Experts are dubious that it is possible for trace exposure to such drugs to cause
illness, not to mention an overdose. But at the time, the Pennsylvania corrections
agency was in a full-blown panic. All state prisons and their mailrooms were locked
down.Officials believed that there were drugs being sent via the Postal Service,

that the prison mail was, n the words of Sen. Bob Casey (D-Penn), “saturated in
fentanyl”

‘Within weeks of the 2018 lockdown, the Pennsylvania Department of Corrections
inked an emergency no-bid §15.8 million contract with Smart Communications for
‘what was then the company’s newest innovation: MailGuard, mail digitization
software. Letters would be sent to Smart Communications instead of the prison,
which would scan them and provide inmates a digital copy — in theory cutting off
the flow of contraband.

About

About Smart Communications

o 008 b e e e ey
e gt e 5 o o o 3

e e g bt o
A e ol o e

o
I

‘The real moneymaker for Smart Communications isits messaging technology. (via

‘SmartCommunicationsus)
‘The Pennsylvania contract represented a big break for Smart Communications,

“That was when they started to really build their business,” said Bianca Tylek, the
founder and executive director of Worth Rises, an advocacy group focused on
prison industries. “After [Smart Communications)] got that contract, that practice
started to spread around the country” Prisons and jails in more than two dozen
ather states now digitize their mail.
Before the Pennsylvania contract, Smart Communications was “basically on the
verge of extinction,” Logan would later testify in court. The private-equity-owned
prison telecom giants — companies like Securus and Global Tel Link — were
‘moving into prison email, squeezing Smart Communications out of the market.

‘Mail scanning changed everything While not particularly profitable on its own,
Smart Communications used the technology as bait to win bigger contracts by
‘bundling MailGuard with the company’s phone and messaging services.

“MailGuard was the Trojan horse; Logan explained in court this February. “If you
‘need MailGuard, you are going to have other services exclusively by SmartComm.”

‘Those other services are the real moneymakers in the prison tech business: Emails,
video chats, music streaming, all provided on physical tablets that inmates must
buy. Messaging income alone (the 50 cent charge per email) brought Smart
Communications revenue of more than $25 million annually as of 2022.

“We actually... make more money by giving [MailGuard) away for free and getting
all the revenue-generating services Logan testified.

While mail-scanning technology was an important point of entry to new profits for
the company, its impact on incarcerated people i to further sever them from the
outside world. Instead of handwritten letters from their loved ones, people in
Pennsylvania’s prisons receive digital scans, some so poorly rendered that they are

egible.

Even when readable, there's a difference between receiving a birthday card or
child's drawing that you can hold in your hands and one thatis scanned ina
warehouse in Florida, sent to you digitally, and then destroyed. As one mother
‘whose son is incarcerated told The Nation, “You cannot scan or copy the tears ofa
loved onel”

* -
g e (VR

Smart Communications claims MailGuard “completely cuts off the last conduits” of
contraband. (via SmartCommunications.us)

“One of the greatest predictors of whether or not someone is going to successfully
reenter society after their release is whether they have strong family and

friendship connections that they can rely on as they work to reestablish their lives,”
said Mike Wessler, communications director at the Prison Policy Initiative, a
research group that closely tracks prison technology and its impacts. Mail scanning
was just one example of the ways that privatized prison services can erode those
ties, Wessler explained. So, too, does paying exorbitant phone and messaging costs,
‘which send prisoners and their families into debt.

“These millionaires have found a way to squeeze more money and sever these
‘connections that are so important;” he said. That, he said, was “what those yachts
represent”

Despite the fervor that won Smart Communications its Pennsylvania contract, it
not clear that mail digitization solves the problem of drugs entering the prison
system. In 2023, five years after the state started mail scanning, a Pennve report
found that people inside Pennsylvania prisons are testing positive for drugs atan
even higher rate than in 2018.

That leaves one clear beneficiary of the technology: Smart Communications.

“They've just inserted themselves as a middleman and are taking money off the
top,” Wessler said.

Logan argues that his innovations — prison email in particular — have helped to
‘connect people who are incarcerated with their loved ones on the outside.

“Ilet inmates use my kiosk system that I paid for, built, I designed, and all 1do is
ask them to pay the same amount that they would pay the US. Postal Service —
only they get to instantly communicate with their family;" he told The Lever.

‘These systems have made Logan rich. His company’s growth since the 2018
contract has been rapid. Smart Communications now operates in 29 states, in over
100 jails and prisons. Between 2021 and 2023, its revenue jumped from §32.3
‘million to $56.2 million. Last year, he recorded a salary of $1.2 million (which he
says he has since forfeited, given his legal troubles).

‘Around that time, Logan bought his superyacht.
“Borderline Criminal”

There came a moment, in the early days of Smart Communications, when Engelke
began to feel nervous about the Logans’ handling of finances, a story he told
several times in court depositions. Back in 2010, he says, he lent some money to
‘Alexis Logan. Some time later, he tried to recoup it,only to discover that her
‘mother, Janice, had allegedly used the cash on a face-lift. Jon Logan’s attorneys
also allege in court pleadings that family members used company money for
“cosmetic and medical procedures”)

From that point forward, Engelke says, he was distrustful of the family.

“I was very uncomfortable with the way they were taking money out of the
company and abuse of credit cards, things like that,” Engelke said ina deposition.
still, he too had his eye on future riches: “l want to make millions with you, then
party like a rock star on our yacht!” the investor wrote to Jon Logan in a 2010 email.
But he never saw the millions or the yacht. By the time Smart Communications
began to take off in 2018, Engelke had been cut out of the company. He maintains
that he is a 10 percent shareholder and has spent the better part of the last decade
suing Smart Communications and the Logans to get his slice of the pie.

“Iwas the sole investor at the beginning,” Engelke told The Lever. “I kept the
company alive by loaning substantial amounts of money for expansion.”

So far, he has been outmaneuvered, and Smart Communications has remained a
family business.

‘The Logans contest who among them rightfully controls the company, but all of
them have been spending its money. This is made clear in court records, in which
Jon Logan and his mother trade dueling accusations about the other's “corporate
waste?”

Thereare the cars Jon Logan bought: the Rolls-Royce, the Ferrari, the Lamborghini.
But his father, too, was allegedly buying cars with company cash before he died,
includinga $100,000 BMW as well as two Stingray Corvettes.

Janice accuses her son of wasting company money on food and travel — a $1,600
sushi dinner, a $10,000 ski trip to Colorado, a $3,000 fishing charter — and on
yacht trips. Jon accuses his parents of spending $150,000 on diamond jewelry. His
‘mother points to his luxury $1.5 million condo in downtown Miami and a $4
‘million waterfront home in Tierra Verde. Jon claims his mother and sister secretly
bought a $1.2 million vacation home in Michigan with company funds, and that his
sister was charging personal expenses to company credit cards for years after she
left her position there.

Then there is the Convict. The $10 million yacht, which the company owns, costs
510,000 a month to harbor at a marina in Miami. According to court pleadings,
Logan employs a full-time captain, who is paid a six-figure salary, and a full-time
deckhand. One person who worked on the Convict described to The Lever the parties
Logan was “always hosting” on the boat: classic *party-scene Miami,” they said.

“Jon has treated the company’s resources as a personal piggy bank and grossly
‘wasted corporate assets,” his mother’s attorneys wrote in an August 2023 court
filing

Such extravagance, though, is in some sense a pillar of Smart Communications”
business. The company sells its technology in part by promising a taste of the
“resortlife” that prison phone calls can buy. To its clients — sheriffs and prison
officials — Smart Communications offers cruises and all-inclusive retreats at
Florida resorts, in addition to generous cuts of the revenue from its prison services.

In 2022, Smart Communications came under scrutiny after The Appeal reported
that the company had offered several sheriffs a complimentary cruise that “sails
out of Tampa Bay to the Caribbean” In some cases, the cruise was stipulated in

contracts that jails signed with Smart Communications. At the time, Logan said
that there had been no cruise to the Caribbean. “This event never came to fruition
and has never happened,” he told The Lever.

‘What have taken place are Smart Communications’“summits retreats for clients
in Clearwater Beach, Florida (“famous for its white sands and clear blue waters,” the
company advertises). According to an itinerary of one of these events from 2022,

the “Elite Sheriff’s and Leaders Summit attendees were treated to a three-day,
all-inclusive stay at the Hyatt Regency Beach Resort & Spa, where rates start at
about $600 a night. Activities included dinner ata local steakhouse, spa
treatments, golfing, and a “sunset boat cruise””

Tnvitation Awaits

DIFFERENT CULTURE - DIFFERENT APPROACH - DIFFERENT OUTCOME

Smart Communications advertises all-inclusive “leadership summits” at a resort in
Florida. (via Smartsummits2022)

According to emails shiained by The Lever, the company extended a similar offer in
September 2020 to Major Shaun Klucznik, the jail administrator at the Hernando
County Sheriff’s Office in West Florida.

“We will take you out to eat, put you up in the Hilton Clearwater Beach Resort,a
Smart Communications sales representative wrote, offering “a choice of fishing or
golf and women having a beach excursion” as el as “a Booze Cruise in the gulf”

“Iappreciate the offer but we cannot participate in events like this;” Klucznik
replied.

“Well darn!” the company’s sales representative wrote back. “Just wanted to show
appreciation to our clients!”

In May 2024, the sales representative again reached out to Klucznik, who by that
point was alfo serving as vice president of the board of the American il
‘Association, ajail industry group. That spring, the association was holding its
annual conference in Fort Lauderdale. Smart Communications, the representative
‘wrote, already had “something special planned for the board” — but the company
'had an additional offer for Klucznik, a “once in lifetime experience”: a “hospitality
event” on “our 100 ft private yacht” (Klucznik says he also declined this
proposition.)

In response to questions about the summits, Logan said that the events “bringin
outside educators for corrections professionals that teach classes that contribute to
agency-required accreditation training hours each year, as well as showcase Smart
Communications’ newest technologies of the future”” Attendance, he said, is “open
toall correctional professionals and has no relation to current, past, or future
business involvement with Smart Communications

Other competitors and prospective clients have raised ethical concerns about the
overtures. “We felt the proposal was borderline criminal and definitely was
‘unethical,” one county jail administrator in Arkansas said of their dealings with
Smart Communications. The 2019 contract bid included a promised “three-day
cruise to Mexico” and an “immediate” $100,000 payout for the county, no strings
attached. (Logan called the comments an “intentional mischaracterization” made
amid an ongoing legal dispute between Smart Communications and another
vendor)

One rival of Smart Communications complained that the company was offering
‘gratuities, which can be illegal, to win contracts, according to reporting from The
Appeal.

The legality of such steak dinners, cruises, and hotel stays “at the local level is
dependent on state ethics laws, which vary;” said Aaron Littman, a professor at the
University of California, Los Angeles School of Law, whose research has focused on
sheriffs and jails. But he called the offers “really troubling”

Smart Communications’ brazen method of courting sheriffs, Littman said,
highlighted just how little external accountability exists for sheriffs and local jail
systems, despite the potential for conflicts of interest with vendors. “Their
insulation from public oversight is really on display here;” he said.

The Lever reached out to 18 sheriff's offices and jail administrators that contract
‘with Smart Communications asking if they had participated in retreats or cruises.
‘Al 12 that responded said they had not, although some acknowledged receiving the
offers. The rest did not reply.

“Storm Clouds”

“1am not one to fuck with on what I created with sheer willpower and brains” Jon
Logan wrote to his father in September 2022, weeks before his death. “If you,
Janice, or Alexis try to take anymore [sic] from me, 1am prepared to o things the
‘normal human could never fathom”

‘As his health declined in the fall of 2022, Jim Logan had started making
preparations for his death and the succession battle he expected was to come.
Although he had taken a back seat in company operations in recent years — partly
due to his reported struggles with alcoholism, which a Florida judge concluded had
been “getting the better of him" by the end — father and son still owned 50 percent
each of the company shares.

Jon Logan wanted to buy his father out. “I want a simple contract and a simple
buyout and clean separation,” he wrote in the September email. His father refused.

Instead, days before a risky surgery, the elder Logan transferred his shares in the
company toa trust that he left in the hands of his wife, Janice. He wrote his son
back days later, quoting the earlier email: “Most humans could never fathom a son
‘who says that to his family for any reason, let alone a son sitting atop his
510,000,000 yacht, next to his $2M condo, with a Rolls, a Lamborghini, and Ferrari
parked at his $5,000,000 beach house. Exactly what did your family take from
yow”

Two different attomeys representing Janice Logan did not reply to multiple
inquiries from The Lever for this story.

In his parents’ telling, Jon Logan had gone to extraordinary lengths to convince his
father to hand over his shares of the company. That included allegedly threatening
them with a firearm. Jim Logan, in an enail, claimed that his son had “broken into
our home and held us at gunpoint demanding that I sign my shares over,”in
addition to vandalizing his parents’ cars and sending death threats.

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Logan says this s “a false, baseless, zero evidence claim” that his mother is using to
‘win the court’s sympathy. Despite the conflict, his father had been his “best friend,”
Logan told The Lever. “I don't think anyone could blame me for not being pleased
that some of the worst communications I've had with my dead father now are
being publicly displayed and rummaged through,” he said.

Jim Logan died in October 2022, leaving Janice Logan, through the trust, as a 50
percent shareholder of Smart Communications. (Jon Logan claims that his mother
xemoved him from the trust, leaving only herself and his sister as s beneficiaries.)
Ever since, Janice and her son have been battling over the company’s millions, a
fight that has turned increasingly ugly.

Initial negotiations between the two stalled after Jon Logan offered his mother a
520 million buyout, which she refused, instead demanding $100 million, according
to text messages between the two, “I said... 'Why would I accept $20 million?”
Janice testified at a February trial. “And he got real ugly with me and used language
Tdon't use. So 1 just hung up on him. Instead, she sent him a letter demanding,
among other things, that he sell the Convict and give her control over the
company’s spending.
Janice Loganlives in a $4 million mansion owned by the company, a gated villa
with a home movie theater, stables, and an indoor pool with a waterfall. I lies on a
20-acre property on the outskirts of Sarasota, alongside an expanse of wild Florida
‘marshlands and longleaf pine forest. This spring, Logan filed for eviction against
his mother, demanding that she pay $35,000 a month in order to stay in the home.

Jon explained to The Lever that he wants to sell the property: “When the company
‘owns the asset, the company ought to have its right to do what it wants with the
asset; he said.

S0 far, the courts have mostly rejected Jon Logan's attempts to wrest back contral of
the company. A Sarasota judge intervened and stopped the eviction case in July
2023, allowing Janice o stay in the mansion. Jon then attempted to move some of
Smart Communications’ subsidiaries to Delaware, seemingly to escape the Florida
courts. A Delaware judge — noting the “alarming nature of the allegations” in the
Florida case — froze the proceedings.

Then in November 2024, days after a Sarasota probate judge had set a date for trial,
Smart Communications filed for bankruptcy, claiming that it was in tens of
‘millions of debt to a Delaware company owned by Jon Logan. On Feb. 26, judge
also blocked that case, sending it once again back to Florida court, where the
Sarasota judge has isstied several rulings in favor of Janice.

“Jon Logan here has spite and animus towards his mother and his sister, and that’s
what's driving decisions, not business judgment, not what's good for the company,”
the judge said at a recent hearing.

“We haven't been getting a fair shake with these judgesatall, and it's evident,”
Logan said of the litigation. In a subsequent email to The Lever, he said he was “a
victim of terrorism through the legal system,” and that his mother and sister were
trying to “extort” money from the company.

Thereare, too, other “storm clouds on the
horizon,” as one judge put it. In 2023,
former President Joe Biden signed the
‘Martha Wright-Reed Act into law, which
directed telecom regulators to cap rates
that prison phone providers, including

®5mnrt Smart Communications, could charge.

Tommuricatons Although prison telecom companies and

THE FUTURE OF CORRECTONS 18 HERE states have flooded the courts with
litigation to stop them, the rate cuts went
into effect in November 202

The Corections
ndusrys
it Mulifanction,

sl megred It is completely gutting the business
Qfeder Wearbie model of providers in our space” Logan
testified in court in February. The rules
required the company to cut fees, which,
hesaid, represented a profit loss of “half a

‘SmartWatch™

‘million dollars a month”
Yet Smart Communications has found success through the years by identifying
‘new, unregulated corners of the prison market.

“Ithink that's where Smart Communications was ahead of the game with some of
their technology,” Wessler said. “They were moving into these unregulated market
spaces before many of the other major players in the prison phone industry”

They have been, in other words, a bellwether of sorts in the prison technology
‘market.

Smart Communications has pivoted to smartwatches. (via Linkedin)

Where is Smart Communications pivoting now? Despite the legal drama, the
‘company has been on the road advertising its flashy new products, marketing
them at correctional industry conferences around the country: a supposedly
first-of-its-kind smartwatch for inmates, prison exercise bike. A recent
‘PowerPoint presentation included in court documents advertising the company’s
latest innovations looks, a first glance, like the lyer for a yoga class, featuring a
‘man standing in a grassy meadow, staring at an amorphous orb of ight.

“What is the next Revolution of Corrections?” it asks. “Mind. Body. Spirit. Smart
Communications welcomes you to the future of incarceration.”

welcomes you to the future of incarceration

Smart Communications calls smartwatches and exercise bikes the *future of
incarceration.” (via court documents)