New York City’s Five Families, hereafter referring to the five major Italian-American Mafia families, Bonanno, Colombo, Gambino, Genovese, and Lucchese, have seen better days, with better days defined as being better from the perspective of a member of one of the Five Families , which in turn means profiting from their various organizational activities. For its part, the Colombo Family began its not-so-graceful decline with the life imprisonment of its late head, Mr. Carmine Persico, in 1987, and the ensuing internecine war between Mr. Persico’s loyalists and a faction led by Mr. Victor Orena. Mr. Orena continues to serve a life term in prison pursuant to his 1992 criminal convictions. Mr. Persico died in 2019 after leading the family from Federal Prison for more than three decades. The details of the decline are less important than the decline itself. No story better captured the decline of the family than a 2021 report on the arrest of Mr. Ralph DiMatteo, who is alleged to be the consigliere of the Colombo Family. He was caught not because of a snitch, but because of his son’s Twitter post. Ms. Rebecca Rosenberg of the New York Post detailed the circumstances leading to Mr. DiMatteo’s surrender to authorities:

A high-ranking member of the Colombo crime family wanted in a federal racketeering case surrendered Friday — one day after his son posted a photo to Twitter of him standing in a glistening swimming pool in Florida.

Rebecca Rosenberg for the New York Post

That is right my friends. Even the mafia cannot log off. To be sure, it sounds like some of the Five Family honchos and their immediate family members have problems that would be relatable to large swaths of the population. (I hope they have not also developed the “like” verbal tic.) Over-sharing. Life as a reality TV show. Et cetera. For his part, Mr. DiMatteo had previously made an escape befitting of a Colombo member of his rank and station:

The 66-year-old mobster took off to Florida one day before the feds busted his 13-co-defendants on racketeering, extortion and other raps related to the infiltration of a Queens labor union.

Rebecca Rosenberg for the New York Post

That is good stuff. One would have to venture that Mr. DiMatteo had someone inside law enforcement who tipped him off, prompting his very timely escape to Florida.

Alas, Mr. DiMatteo’s son just had to post a picture of dad “shirtless, half-submerged in a turquoise-colored pool, sporting a gold crucifix around his neck as he stare[d] directly into the camera.” You will note in the photo that comes with the article that Mr. DiMatteo really was staring directly into the camera. Not only is his face clearly visible, so too is a large tattoo on his right arm (I will venture his tattoo was an identifying feature also known to law enforcement). There is no surprise that the Twitter posting ruined what was likely a well-executed escape (albeit Florida is not the most creative escape destination in this particular context, being where New York/New Jersey mafiosos are known to “retire”).

We are told that Mr. DiMatteo’s son deleted the photo. However, as Mr. David Amoruso of Gangsters Inc. noted, “what happens on the internet, stays on the internet for everyone to see.”

I had originally planned to share a link to the cautionary tale of Mr. DiMatteo in our newsletter’s Around the Web section. However, I upgraded it to New Leaf Journal article status when I an update to the saga appeared in my feed reader, courtesy of the New York Post’s metro RSS feed. I quote from the article titled High-ranking gangster Ralph DiMatteo, who lounged shirtless in a pool while on the lam, pleads guilty to racketeering:

Ralph DiMatteo, who prosecutors say was the clan’s consigliere, admitted to extortion, conspiracy and money laundering from 2020 to 2021 in Brooklyn federal court — including a scheme to threaten a union official identified only as ‘John Doe No. 1.’

Kyle Schnitzer for the New York Post

(Note: A “consigliere” in the world of Sicilian mafia families denotes the highest ranking trusted advisor to to the boss.)

Mr. DiMatteo faces several years in prison:

Judge Hector Gonzalez said the guidelines for sentencing DiMatteo range between 41 and 51 months in prison.

Kyle Schnitzer for the New York Post

What lesson can we draw from the story of Mr. DiMatteo? The easy lesson would be to not engage in criminal racketeering. I would personally recommend compliance with that rule. However, simply leaving readers with a lesson like “don’t do crime” would hardly be exciting. I prefer to approach seemingly obvious issues from unusual angles. We can draw some more important lessons from the story.

Firstly, if you are trying to go incognito, I would recommend not posing for photographs. If you must pose for a photograph, I would recommend not posing for a photograph taken by a phone with internet connectivity, even if it is running a secure OS. In fact, you should probably be careful about having any of those phones on you at all. Perhaps consider using a disposable camera (do they still sell those?) and holding off on developing the photos until things calm down.

(Again, you can limit your concerns to the ordinary sorts of privacy issues I discuss on The New Leaf Journal if you refrain from criminal racketeering.)

Secondly, just because you took the photo does not mean that you need to post it to Twitter. Believe it or not, you do not need to document your entire life on social media. Your life need not be a reality show. I detailed my thoughts on the matter with respect to parents chronicling the lives of their children online. This Colombo story made me realize that we may need to cover children documenting the lives of their parents online.

(If you do not engage in criminal racketeering, your problems will be limited more to over-sharing than having to surrender to Federal law enforcement to avoid having your home or hotel suite raided by heavily-armed officers of the United States Marshals Service.)

Thirdly, it may help to take a step back and ask yourself what people did before they could instantly share their lives with random internet people. I know not how old Mr. DiMatteo’s son is, but Mr. DiMatteo, who is age 68, surely has some frame of reference of what the world was like before the majority of people were walking around with internet-connected cell phones. I have this frame of reference and I am significantly younger than Mr. DiMatteo. Mr. DiMatteo would have done well to draw on his own life experience (he would have also done well to not engage in criminal racketeering) and the wisdom of his forefathers (if he absolutely insists on engaging in criminal racketeering). To be sure, many prominent Colombo figures have been sentenced to lengthy terms of imprisonment. But would any have been thwarted by their son tweeting their whereabouts? Would this have been the downfall of Carmine Persico or former Colombo executioner, Gregory the “Grim Reaper” Scarpa, Sr., in a different age? I think not.

(I have been told that even five-year olds can be taught to avoid this fate.)

It may seem strange to say that normal people engaged in ordinary daily activities could learn something from the story of Mr. DiMatteo, who has undoubtedly been living a very different life than your average New York City resident. But I see so many people glued to their phones, sharing their every staged moment (and the moments of their kids). Are Mr. DiMatteo and his son that different from the questionable course of actions which led to a certain teenage TikTok (TikTok should be banned) starlet being confronted with a dangerous stalker? Yes, in terms of racketeering, but no in terms of the path to danger.

I can state with some confidence that Mr. DiMatteo and his son would have enjoyed their Florida sojourn much more without phones and Twitter than with (especially those relaxation times since I will venture that this was intended to be a sort of business trip for Mr. DiMatteo). With Father’s Day recently behind us, perhaps this story is a lesson to spend time looking at your loved one with your eyes instead of through the lens of your phone. That Mr. Matteo’s arrest and incarceration was likely inevitable should have made it more important, not less, to live in the moment. They could have engaged in productive leisure instead of social media posturing. (Did I do a good job adding sentimentality to this story?)

Know when to log off.