“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 in the 1970s. 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 in prison was roughly the same as in the world beyond. By the 1990s, 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 $1 a 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 1970s 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 more phone calls would be made.

By the mid-aughts, prison telecom had become highly consolidated, with just two firms controlling most of the market. There was also regulation on the horizon: the nation’s telecom regulator, the Federal Communications Commission, was poised 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.

It was 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, who at 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.”

In 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 inquiries.) 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.”

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 owned a marina and a few different auto businesses. But court records indicate that, by 2009, he was in hot 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.)

As 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, so as not to sink the empire.”

Engelke also began to have concerns about how corporate dollars were being spent. At lunch with Jon Logan early on, he recalls confronting the young executive about a company-expensed trip to the Florida Keys.

“This is my fucking company,” Logan shot back, according to Engelke. “And if I want to take a girl to the Keys for the weekend and charge it to the company, I’ll do so.”

(“Did you ever investigate whether Jon Logan took this trip to the Keys using [company] money?” a lawyer asked Jim Logan years later. “I didn’t,” he replied.)

There was another matter: Jon Logan was on probation for a 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 “life 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.

But he was closer with his father, and as an adult — following a stint doing professional motocross — he began working with him on a car-dealership venture. By 2007, when Logan was twenty-five, 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 out a restraining order against him. Then, in November 2007, a 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 cell-phone 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.”

In 2008, Jon Logan pleaded guilty to a 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 eleven months in county jail.

It was 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. I know 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.”

Logan claims that he did not write the Craigslist ads — “I was intentionally framed,” he told us — 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: “I want to do a tongue-in-cheek name on my boat, that’s my right. I earned it.”

“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 room for potential drug exposure forty-eight times. Prison guards were falling ill as they processed mail and searched jail cells. In fact, they were falling ill all around the country. The incidents fed into a 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 mail rooms were locked down. Officials believed that there were drugs being sent via the Postal Service, that the prison mail was, in the words of Sen. Bob Casey (D-PA), “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.

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 other 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 is 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 illegible.

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 that is scanned in a 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 of a loved one!”

“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’s 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 PennLive report found that people inside Pennsylvania prisons are testing positive for drugs at an 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.

“I let inmates use my kiosk system that I paid for, I built, I designed, and all I do 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 twenty-nine states, in over one hundred 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 facelift. (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 in a deposition. Still, he too had his eye on future riches: “I 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.

“I was 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.”

There are 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, including a $100,000 BMW as well as two Corvette Stingrays.

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 $10,000 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 “resort life” 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 theAppeal 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 us.

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 at a local steak house, spa treatments, golfing, and a “sunset boat cruise.”

According to emails obtained 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 well as “a Booze Cruise in the gulf.”

“I appreciate 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 also serving as vice president of the board of the American Jail Association, a jail 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 a 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 “bring in 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 to all 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 eighteen sheriff’s offices and jail administrators that contract with Smart Communications asking if they had participated in retreats or cruises. All twelve that responded said they had not, although some acknowledged receiving the offers. The rest did not reply.

“Storm Clouds”

“I am 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, I am prepared to do 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 to a 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 $10,000,000 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 you?”

Two different attorneys 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 email, 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.

Logan says this is “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 removed him from the trust, leaving only herself and his sister as its 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 $20 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 I don’t use. So I 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 Logan lives 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. It lies on a twenty-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.

So far, the courts have mostly rejected Jon Logan’s attempts to wrest back control of the company. A Sarasota judge intervened and stopped the eviction case in July 2023, allowing Janice to 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 February 26, a judge also blocked that case, sending it once again back to Florida court, where the Sarasota judge has issued 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 judges at all, 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.

There are, 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 Smart Communications, could charge. Although prison telecom companies and states have flooded the courts with litigation to stop them, the rate cuts went into effect in November 2024.

“It is completely gutting the business model of providers in our space,” Logan testified in court in February. The rules required the company to cut fees, which, he said, represented a profit loss of “half a million dollars a month.”

Yet Smart Communications has found success through the years by identifying new, unregulated corners of the prison market.

“I think 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.

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, a prison exercise bike. A recent PowerPoint presentation included in court documents advertising the company’s latest innovations looks, at first glance, like the flyer for a yoga class, featuring a man standing in a grassy meadow, staring at an amorphous orb of light.

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