Underworld Winners and Losers

Regardless of the business entity or activity that people engage in, in every facet of life, there are always winners and losers. Some guys have a solid knack for business and a ‘"Midas-touch," so to speak, who are very good at both creating successful new businesses and keeping existing businesses afloat with a bottom line solidly in the black. Other guys are so business savvy and astute in legitimate business that nearly everything they touch turns to gold.

Life in the mob is no different.

If anything, the winners and losers of mob life become even more pronounced and evident when we speak about the underworld. The winners and losers also become more easily identified and stand out as time goes on by certain key benchmarks on how these knock-around guys end up in life, both good and bad.

Successful mob careers are really no different than those of legitimate businessmen because at the end of the day, when all the smoke clears, you can usually tell who ran first coming "into the money" and ending up in the mob winner's circle, and who ran last and was left in the dust as brokesters and financial failures, for lack of better terms.

Usually, when a guy is a savvy big moneymaker, regardless of whether that particular guy deals in the upper world or the underworld, that success will be evident by the house he lives in, the automobile he drives, the clothes and jewelry he wears, and the restaurants and other places he frequents.

Likewise, when a businessman or mob guy is struggling and not earning well, that, too, will show by the house he doesn’t live in, the automobile he doesn’t drive, the clothes and jewelry he doesn’t wear, and the places he cannot afford to frequent. The "proof is in the pudding," as the old saying goes.

When a legit business guy makes it big, it’ll usually show. You can usually tell by the way he runs his business if it is a success, and if he’s making big bucks.

Over his entire lifetime and business career, if he has consistently earned big money through his enterprises, such as a popular restaurant that makes money, a very successful garbage company with numerous trucks, or another type of solid enterprise, you can bet that he is earning a good dollar.

Frank Costello

Guys like that usually live in a very nice home in one of the upper-scale neighborhoods and drive an expensive automobile. He’ll also usually dress well in expensive threads, and when he goes out socially, he’ll dine in the better restaurants and clubs. It’s only common sense.

Wiseguys are generally no different, especially today, where, if they’re gonna risk their balls, most of them wanna enjoy the finer things that this life has to offer along the way.

The days and images of the old greaseball mafia boss stuffing millions under his mattress while living in a hovel or nondescript little apartment to hide his true wealth are long gone. You can bet that 99.9% of the fellas who have big money wanna flaunt it, regardless of whether they operate as legit businessmen or operate illegitimately in the streets.

Very few people, regardless of their vocation, will play that humble routine and cry poor mouth if they can earn big bucks and can afford a better lifestyle for themselves and their wives and children.

The success of a legitimate businessman is usually measured by the success of his business, the money he earns annually, and the lifestyle he lives. Likewise, the success of a wiseguy and hoodlum is largely measured the same way, with one or two caveats thrown in.

The success of a "street guy" can usually be assessed the same way except that because of the very nature of their "business" and the perils they face daily, the number of arrests they’ve taken over the years, and the jail time they may or may not have served, also plays a big part in determining the so-called "success" of the racketeer. It’s simply not enough to have earned a lot of money during his years on the streets.

To be considered a successful mobster, that same guy would have had to either not have gone to prison or, in the alternative, have served a minimal amount of prison time. To have been able to make a lot of money, and yet to have served either no jail time or a minimal amount of jail time, constitutes a "winner" in that life.

If the fellow in question was repeatedly arrested and jailed on numerous occasions during his career like a revolving door, then whatever financial success he may or may not have achieved means little in the true scheme of things. The ability of the mafioso to have earned well but to have spent only a few years behind bars for his criminal activities is the true benchmark of a winner in “The Life.”

Regardless of what official “position” that man may have achieved during his time spent in the rackets, whether he was an associate, a soldier, captain, underboss, consigliere, or rose to became the Family boss, his ability to have made money (and lots of it,) coupled with his ability to have avoided arrest and incarceration, is typically the real goal of any true street guy or wiseguy. For if he wants to call himself a “wise” guy, then he’s gotta be wise about how he operates as well.

Mafia aficionados who follow the careers of mob guys will note just how many of them may or may not have made big money in their lifetimes. But you must also take note of the prison time these same men have spent behind bars in their lives.

There are very few who rise to the leadership of a Family who haven't spent literally decades behind prison walls. And we’re not talking just a few years here or a five-year bid. I’m speaking about them having spent over 20, 25, 30, 35 years or more in a jail cell. Bosses like Carmine Persico have spent over 45 years of their life in jail, and he ended up dying behind bars. His beloved son, Alphonse, is currently serving a life sentence with no chance of parole whatsoever. And these two men are not alone.

The list is long and getting longer of top mafiosi and noted racketeers who have served many decades behind steel bars and cement walls. Many of those same men ended up dying behind prison walls, never hitting the streets again.

And many others end up serving 8, 10, 15, 17, or more years in the jug as well. These are big numbers. It may not aggregate to "many" decades behind bars, but, nonetheless, it’s still a helluva lot of time out of their natural lives to be taken off the streets.

And guess what? Most of those very same guys ended up broke. Even the ones who may have originally gone to prison with significant bankrolls. Why you ask? Because most of them had wives, children, and girlfriends who still needed to be supported while they were away at prison.

The home mortgage and utilities still need to be paid. School tuition, automobiles, and car insurance, food put on the table daily, clothes, medical expenses, etc. Life on the outside doesn’t simply stop and freeze up because you went to prison. Everything continues. And as the "breadwinner" for your personal family, you are still responsible for their continued well-being.

So, even if a guy is lucky enough to have a big bankroll before he gets sent away, if he’s doing a significant bid like 10-15 years (or more) the money just has a way of quickly evaporating into thin air….and that's taking for granted that the fellow in question had a big bankroll, to begin with. Believe me when I tell ya that most of them don’t have that desired bankroll.

So here is my personal assessment of what I’d call a “winner” in the so-called “Life.” If the fellow in question earned millions of dollars for himself, or at least many hundreds of thousands that he saved and put to good use while never doing a jail bid, or in the alternative, he was lucky enough to have never served more than five or six years total behind bars in his lifetime, then, in my opinion, a guy like that could put in the “Winners Circle” of gangland.

But regardless of how much money that man may or may not have earned (despite the common mistaken belief that all mobsters are wealthy), if he spent many years in jail, then any so-called “win” he may have achieved became a “loss” because the years stolen from his life are worth much more than any amount of money, or perceived ‘so-called’ power, he may have had on the streets.

What good does it do him? I’ll answer my own question for that last one. It does him no good! He has essentially wasted his life. And although most would never admit it in public, behind closed doors most fellas will tell you in hindsight that they wasted their lives.

Side Note: I will not even bother to address the tremendous collateral damage and fallout suffered by the immediate blood families of these wiseguys who spend decades behind bars. More often than not the families are destroyed in many ways; wives have nervous breakdowns, many children became very wayward without their dad’s presence in their lives, and have emotional issues, the family home is lost to the bank because of mortgage arrears, etc. It is never a cakewalk for the families I assure you.

Then of course there were the winners. The fellows who were the true winners. Guys who have indeed been able to achieve exactly what I have described above. But those are the fellas who mob aficionados will never ever read about, guys whose names they are not even familiar with more times than not.

It's because these same mafiosi and racket guys are the ones who successfully slipped through the cracks of law enforcement. The ones who made the big money never got their names in the newspapers and spent little to no time in jail.

They are not the Carmine Galantes or the John Gottis of the mob. They are the mob guys “you never heard of.” And that's exactly the way they liked it!

Until the next time...”The Other Guy!”

Underworld Winners and Losers

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