Author: Grumpy
A promising American chased a cause, crossed an ocean, put on a Russian uniform, and died in Ukraine. This is the stark, uncomfortable arc of Michael Gloss.
Hook: From Idealism To A Battlefield No One Expected
Ah, kids…
Proverbs 22:6 says, “Train up a child in the way he should go,
And when he is old he will not depart from it.”
That’s in the Book, and I understand the gist. In general, irresponsible parents spawn irresponsible kids. Almost every serious smoker I ever met had at least one smoking parent. Kids model the behavior of their parents, even when they are rebellious, distant, or cruel. Oftentimes, it is because of those things. By contrast, put in the work as a parent and you will afford your offspring the best opportunity to succeed.
Regardless of how they are raised, kids are like little homemade boats. You carefully craft that vessel as best you can, but at some point, you have to push that thing out into the pond. Once that’s done, your kid is making his or her own decisions. There’s no turning back.
I’ve had to do that three times myself. Each iteration was comparably excruciating. Watching my kids make some of the same mistakes I did was particularly poignant. Thanks to the grace of God, my three turned out OK. Tragically, however, despite a parent’s best efforts, sometimes that is not the case.
Case Study: How Michael Gloss Slid From Idealism To War
We are about to discuss one family’s absolute nightmare. I’m not making light of it or in any way diminishing the gravitas of the events surrounding this young man’s life and untimely death. In the brief life of Michael Gloss, we see a man who was exploited by the most corrupt regime of the modern age. His death touches on politics, rebellion, and the scourge of mental illness.
As near as we can tell, Michael Gloss started out well. His father, Larry Gloss, was a US Navy Desert Storm veteran who currently works in cybersecurity. His mom, Juliane Gallina, is a US Naval Academy grad who was the first female to lead the brigade of midshipmen. After leaving the Navy, Juliane took a job at the CIA. She is currently the CIA’s deputy director for digital innovation.
I don’t know Larry or Juliane myself. Any deductions I have made come from reading news reports. However, it is a safe bet that Michael was likely raised fairly well. Both of his parents were Navy vets, and his mother is a spy. They are clearly smart, conscientious, patriotic Americans. However, sometimes even with the best of foundations, kids can go off the rails. That’s what happened with Michael Gloss.
Details: From Vienna, Virginia To A Russian Uniform
At some point, Michael became radicalized. No offense, but I can see that in this very space. I’ve been writing these weekly GunsAmerica columns for literally years now. I read every word of the comments. Most readers are insightful, respectful, and thought-provoking. Reading your opinions often makes me rethink my own, which is always a healthy thing. However, a small but statistically significant percentage of you dudes are flat-out nuts.
It is fascinating to ponder why that is. We live in the very earliest throes of the Information Age. Never before in history has the human animal been bombarded with so much raw data starting at such a young age. Personally, I think that’s where a lot of our ADHD comes from. We take newborns and subject them to flashing lights and frenetic sounds every waking minute because that’s the easy way to keep them occupied and quiet. Then they grow up unable to pay attention or manage a steady train of thought. We really should have seen that coming. One side effect of this constant barrage of information is that folks can get emotionally invested in some remarkably spurious causes. There are countless examples.
Case Studies: When Narratives Replace Reality
Charlie Kirk wasn’t a racist in any traditional sense. Any unbiased thinking person who bothers to invest an hour or two listening to the guy talk will draw that conclusion. However, a warped young man driven by sound bites and carefully sculpted narratives got sufficiently agitated as to climb up onto a rooftop with an antique bolt-action rifle and murder him in front of his little girl.
Leftists around the globe have been rioting in support of Palestine. This is despite the fact that Hamas murdered 1,200 men, women, and children in a single day and will flat-out execute you if they even think you might be gay. It’s pretty nonsensical if you think about it.
In the case of Michael Gloss, this poor kid got so agitated over contrived environmental issues and curated online propaganda that he abandoned his life in the United States and made his way to Russia. Once there, he was convinced that he was going to save the planet by enlisting in the Russian Army. In short order, he was sent to Ukraine and killed alongside countless thousands of actual Russians also duped into becoming the Bad Guys in Putin’s bloody war.
The Guy: School, Sports, And A Hard Turn
Michael Gloss graduated from Oakton High School in Vienna, Virginia. While there, he played both football and lacrosse. He subsequently attended the College of the Atlantic in Bar Harbor, Maine, where he majored in human ecology. I wasn’t there, and I never met the kid myself. However, I’d be willing to bet that some of his human ecology professors were pretty politically out there.
Left-wing apologists often suffer from a most peculiar form of cognitive dissonance. Tyler Robinson, the young man who apparently shot Charlie Kirk, grew up in a conservative Mormon family. However, once he got to college, he began dating a man who identifies as a woman. His personal writings expressed outrage over LGBT causes. I’ve lost track of the times I have seen left-wing commentators allege that Robinson must have been some kind of closet MAGA operative. Really? Gee whiz, guys, if it walks like a duck and it quacks like a duck, that’s most likely a duck.
Michael’s obituary read, in part, “Michael grew to be physically strong and tall, thoughtful and principled, and from an early age he used these strengths to protect and guard against injustice of all forms — whether it was on the playground, on the field or in politics.”
Reading between the lines, I’m thinking he likely got radicalized in college before launching on his ill-advised voyage of discovery.
Darker Factors: Mental Health And Manipulation
As I researched this sordid tale, I found references to Michael’s unspecified mental illness. It is estimated that 23.4% of Americans suffer from some kind of diagnosable mental disorder. 5.6% of US adults experience some sort of serious mental illness event each year. At some point in their lives, nearly half of Americans would meet the criteria for mental illness of some sort. I deal with that constantly in my day job. Trust me, those numbers are real.
Anxiety disorders are the most common. Major depression affects around 8% of Americans. Part of that is certainly the result of increased surveillance. In eras past, ADHD was just little boys being little lunatics, while depression was often treated unsuccessfully with alcohol. Regardless of the particulars, in the case of Michael Gloss, this toxic combination of nature and nurture ultimately killed him.
Cannon Fodder: Front Lines, Donetsk, 2024
Gloss signed a contract to join the Russian armed forces in 2023 and was assigned to an airborne regiment. His status as an American citizen who was the son of a CIA officer inevitably earned him a certain degree of notoriety. Regardless, he was deployed to the front lines in Ukraine’s Donetsk region in short order.
The Russian war of aggression in Ukraine has ground on for either four or twelve years, depending upon where you establish the starting point. Both the government of Ukraine and the non-partisan UK Center for Strategic and International Studies (CSIS) placed total Russian casualties in excess of one million troops as of mid-2025. Russian independent media has verified at least 135,000 Russian KIA.
That number is the result of scrubbing social media, scant official records, and documenting physical tombstones. CSIS estimates of Russian KIAs float around 325k, which is tough to get your head around. Regardless of how you gauge it, the war in Ukraine has been a bloodbath for both sides. That doesn’t seem to be getting any better.
On 4 April 2024, Michael Gloss was caught in an artillery barrage during military operations near Donetsk. His father later reported that he was hit while trying to rescue an injured comrade. What scant information that made it back to the States indicates that he bled to death as a result of his wounds.
Key Timeline And Facts: Michael Gloss
| Name | Michael Gloss |
|---|---|
| Background | Oakton High School; College of the Atlantic, human ecology |
| Enlisted | Russian Armed Forces |
| Deployment | Front lines in the Donetsk region, Ukraine |
| Date of Death | 4 April 2024, artillery barrage near Donetsk |
| Aftermath | Public praise in Russia; award and naming reported later |
Hard Truths & Lessons
- Propaganda preys on purpose-seeking youth. It sells certainty, then cashes the check in blood.
- Information overload distorts judgment. Endless feeds can turn causes into obsessions.
- Mental health matters. Untreated issues make manipulation easier and outcomes worse.
- War devours the idealistic first. Once you step onto that field, reality rules.
Ruminations: What Michael Gloss’s Death Should Teach Us
Michael Gloss was known to have suffered from a diagnosable mental disorder, though particulars are vague. Vladimir Putin publicly lauded Gloss by name. Russia named a school in the occupied Donetsk region after him. In August of 2025, Gloss was awarded the Russian Order of Courage. His award was delivered to his grieving parents by US envoy Steve Witcoff. I’m not convinced that brought Michael’s folks a great deal of comfort.
Everything about the sordid story of Michael Gloss is simply tragic. Whipped into an ideological furor, a misguided, mentally ill young man fled to a dictatorship and apparently willingly volunteered to go to war on behalf of a monster. Modern war is horrible, bloody, and shockingly efficient. Michael was subsequently blown to pieces alongside literally hundreds of thousands of similarly misguided young soldiers, all because one dark, twisted man cannot bring himself to say, “Stop.” It still amazes me that, this deep into the 21st century, nations still go to war over the whims of a single deranged lunatic.
Jack “Legs” Diamond was an old-school thug.
He came from the factory broken. Photo: Public Domain
Just what is “stopping power” anyway? One dude strolled nonchalantly into the ER when I was on duty, having taken a 9mm ball round to the pelvis. He was only minimally inconvenienced. Another guy sped away from a drug deal gone bad with the unlicensed pharmacist throwing 9mm rounds his way with vigorous dispatch.
Then he got home and noticed blood. A 115-grain FMJ round had punched through the trunk, back seat and then front seat before embedding in his back fat. This gentleman legitimately did not know he was shot. And then there was the sweet little old lady who caught a .25 ACP round to the neck during a robbery and will spend the rest of her days in a motorized wheelchair. How well bullets perform in the real world is bizarrely unpredictable. And then there was this guy.
The 1921 Colt Thompson got all the press. However, then,
as now, it was the humble handgun that spilled the most blood.
Origin Story
Nobody is really sure what Jack “Legs” Diamond’s real name was. He went by John Thomas Diamond, as well as John Nolan, John Moran and Gentleman Jack. He was born in the summer of 1897 to Sara and John Moran. It was obvious from the outset this little kid just wasn’t right.
Part of that was likely his sordid environment. Jack’s mom, Sara, was frail by nature and died of an illness when Jack was 16. Jack joined a Manhattan criminal gang called the Hudson Dusters soon thereafter. He was first arrested for burglary a year after his mom’s death.
Diamond enlisted in the Army intending to fight in Europe during World War I but lost his enthusiasm in short order. He deserted, was caught and served several years in Leavenworth.
Prison is grad school for criminals. When Diamond was finally released, he was free to pursue his true calling. In 1921, he entered the employ of a professional criminal named Arnold Rothstein. Diamond’s job description included bodyguard and general thuggery.
Jack Diamond’s nickname “Legs” spawned from one of two possible sources. He was purported to be a fairly competent dancer. He also established a well-earned reputation for being able to expeditiously get out of trouble. Somewhere along the way, his associates began calling him “Legs,” and the moniker stuck.
Being a mob enforcer doesn’t have the greatest retirement plan. Additionally, Jack Diamond was a hyperactive lad and a serial womanizer. Despite being married, he carried on a protracted illicit relationship with a prominent New York showgirl named Marion “Kiki” Roberts.
These suboptimal personal habits and the curiously violent nature of his profession synergistically combined to keep Jack Diamond’s physicians gainfully employed. By 1931, Diamond was known as the “Clay Pigeon of the Underworld.”
Normal people don’t have a nemesis. Jack Diamond, however, was not a normal person. His criminal counterpart was the infamous mobster Dutch Schultz. When describing Diamond, Schultz once remarked to his merry mob of misfits, “Ain’t there nobody that can shoot this guy so he don’t bounce back?”
Gangsters used a variety of handguns during the liquor wars of the 1920s. From left to right, we have the Colt Model 1903 .38 revolver, the .45 ACP Colt M1911 pistol, the 9mm P08 Parabellum
and the .32 ACP Colt Model 1903.
A Curiously Hazardous Profession
Prohibition ran from 1920 until 1933. The stock market crash that accompanied the Great Depression kicked off in 1929. The toxic combination of these two events meant there was a great deal of money to be made for those willing to ignore the law.
Diamond saw this as an opportunity and traveled to Europe in search of alcohol and drugs. He returned with barrels of liquor that he had dumped into New York Harbor. Partially filled, these barrels floated low in the water. By studying the tides, Diamond could predict where they might make landfall. He paid local children a nickel apiece to retrieve these containers.
Diamond was the partial owner of the Hotsy Totsy Club on Broadway. With a name like Hotsy Totsy Club, they weren’t hosting Sunday School brunches or teaching underprivileged blind kids to read.
Diamond used his club as a home base for all manner of illicit activities. In July of 1929, Diamond and an associate named Charles Entratta broke up a fight in the club by shooting three of the participants.
Two of the inebriated thugs, Simon Walker and William Cassidy, died as a result. William’s brother, Peter, was badly wounded. In response, the three men’s criminal associates kidnapped the Hotsy Totsy’s bartender, three members of the waitstaff and the cute hatcheck girl. One of the five was later found murdered in neighboring New Jersey. The other four were never heard from again.
There followed arrests for kidnapping, assault and sundry other crimes. Diamond attempted to flee to Europe but was unwelcome in the UK, Belgium and France. Eventually, German police deported him back to Philadelphia.
The first time Jack Diamond was shot, it was with a 12-bore shotgun. This vintage Remington Model 11 is typical of the genre.
A Notoriously Hard Man to Kill
Jack Diamond was the target of at least five assassination attempts. The first occurred in 1924 while he was attempting to hijack a truck full of liquor belonging to a rival criminal gang. Diamond caught a charge of 12-gauge shot to the face and head but recovered.
Three years later, Diamond was pulling bodyguard duty for a proper villain named Jacob “Little Augie” Orgen. While the two men were walking in Manhattan’s Lower East Side, they were confronted by a trio of assailants.
These three shooters opened fire at close range, killing Orgen outright and hitting Diamond twice in the chest. Both rounds passed beneath the gangster’s heart, and he recovered after a protracted hospital stay. Though he undoubtedly knew the men who shot him and killed his boss, Diamond refused to reveal their identities to police. Jack Diamond was a lot of things, but he wasn’t a snitch.
In October of 1930, Diamond was a guest at the Hotel Monticello on Manhattan’s West Side. Three assassins forced their way into his room and shot him five times. The shooters then fled. Diamond, for his part, stopped long enough to drink two shots of whiskey before staggering into the hallway in his pajamas where he collapsed. After two and a half months in the hospital, Legs Diamond was released to sow yet more chaos.
In 1930, Diamond and a pair of thugs kidnapped and beat a truck driver named Grover Parks, who was carrying a load of hard cider for a rival gang. Even if the victim is a thug himself, it was still against the law to beat people within an inch of their lives. In April of 1931, Diamond was arrested for Parks’ assault. Two days after his arrest, Diamond was released on a $25,000 bond.
Five days after that, Diamond was a guest at the Aratoga Inn, a roadhouse near Cairo, NY. After taking a meal with three associates in the roadhouse restaurant, Diamond stepped outside to get some air. Gunmen masquerading as duck hunters opened fire from a parked car and shot him three times at close range. Bystanders drove the bleeding Diamond to the hospital, where he recovered yet again after a protracted stay. By now, he was likely growing weary of hospital food.
Jack Diamond’s weapon of choice was a 4″ P08 Parabellum pistol equipped with the 32-round snail-drum magazine from an Artillery Luger.
Nobody is Immortal
If you’re counting, by then, Legs Diamond had been shot with 10 handgun rounds and an unknown number of shotgun pellets. The rock-hard mobster seemed unkillable. However, on December 18, 1931, Jack Diamond’s luck ran out.
By now, Diamond was staying at a rooming house in Albany, NY. He took dinner out with friends at a local restaurant before partying the night away with his mistress, Kiki Roberts. Come the dawn, Diamond staggered back to his boarding house and passed out on his bed.
Two attackers entered his room soon thereafter with a key. One man held him in place while the other pumped three rounds into the back of his head. The two gunmen fled, but one had second thoughts, ran back to the room and shot him several more times.
Mrs. Laura Woods, Diamond’s landlady, later testified that she heard one of the shooters say, “Oh, hell, that’s enough. Come on.” His killers were never caught.
There was ample conjecture. Some suspected local mafia hit men. Others postulated that the shooters had been crooked members of the Albany police force. Regardless, Legs Diamond was finally well and truly dead.
Legs Diamond was buried at Mount Olivet Cemetery in Maspeth, Queens, NY. Though there was no formal service, there were around 200 people who attended just to gawk.
Two years later, the body of Legs Diamond’s widow, Alice Kenny Diamond, was discovered shot to death in her apartment. Mob watchers suspected she was murdered to keep her from telling what she knew about her husband’s nefarious dealings.
This is the SS Belgenland. In 1930, Jack Diamond took this ship to Europe in search of illicit booze and drugs during Prohibition. Photo: Public Domain
The 9mm P08 Parabellum and the Colt M1911 .45 were both powerful and concealable gangster weapons used during the Roaring ’20s.
Ruminations
Legs Diamond was a killer. His weapon of choice was a German P-08 Parabellum pistol with a 4″ barrel and a 32-round snail-drum magazine. In the years following the First World War, such martial firearms would have been relatively commonplace, having been brought back from Doughboys serving overseas.
The 9mm round was appealing then for the same reasons it is appealing now. A drum-equipped Luger pistol was sort of concealable and offered unparalleled firepower.
So, what are the tactical lessons to be learned from the sordid life and gory death of Jack Diamond? For starters, handguns can be pretty substandard manstoppers, particularly firing ball ammo.
They will certainly do the job, but shot placement and ammunition selection are critical. In a social exchange of gunfire, most any rifle is more effective than most any pistol. At appropriate ranges, most any shotgun is more effective than most any rifle. It finally took 16 pistol rounds and Lord only knows how many shotgun pellets to put Jack Diamond down.
Jack Diamond shuffled off this mortal coil in 1931 at age 34. By the time he finally expired in a pool of his own blood, Legs had seen and done an awful lot of bad things. However, even nearly a century later, he can still teach us a great deal about the art of armed combat.