Most of these guys are lucky to get 8 or 10 years on the streets without getting pinched and doing a long stretch in prison. Who are some notable guys who managed to stay on the streets for decades without a long sentence? Carlo Gambino is the one that sticks out. Who else had a long undisturbed run?

Massino had a decent run, especially for his time period.

A lot of the bosses now are enjoying pretty good runs. It's surprising, but no bodies = less attention.

in italy bernardo provenzano 43 years on the run

Angelo Bruno from the late '50's to his assasination in 1980.

joe batters obv.

Do guys out in Chicago and Detroit have longer free stretches than NY guys on average or do I just hear about it less since I'm in NY?

Heck Raymond Patriarca, Sr had a good run from 1952 to 1984 with just a couple year in jail in the early 70's and his modern day counterpart Luigi Manocchio was on the streets from the early 80's to 2012 and was in the bosses chair from 1996 to 2009. He's 88 and back on the streets after a 30 month sentence for his 2012 conviction for the strip club shakedowns...

Santo Trafficante

Baby Shacks isn't quite back on the street I don't think, I think he is still on federal restrictions but I could be wrong. He's back on the Hill for sure but I imagine once they lift his restrictions he'll be back in Florida for good.

Manocchio is out of the halfway house next month

Joe Bonanno had a decent run.

When we say decent run, what do we mean? I'm wondering who managed to stay free for 20-30 years. Boss or not, just anyone who made money without the jail time that goes with it. Tommy Gambino maybe? I'm sure there are quite a few.

One of the top westside guys or gambinos from back in the day...I would say Richie the boot or patsy conte. If we're talking bosses than ricca and accardo take it

I would say tommy lucchese i believe he was boss from 51 or 52-69 when he died dont recall him even bein locked up cept maybe for contempt altho im sure a more knowledgeable poster can set the record straight..also before he was boss and just a capo/UB dont think he did any time?

As far as longest streak for a capo id have to go withxthe various Genovese skippers that PB has mentioned in the past that i never heard of that im sure had decent runs like larry black, severio santoro, muscarella (know he did a stretch in early 2000's) , jimmy messera and john barbato (again i know both did time but i believe they had decent stretches where they were on the streets)... Pure speculation on my part i defer to more knowledgeable guys and better researchers like ivy to correct me if im wrong

Side note, id love to hear more about genovese skippers like messera, barbato, centorre , santoro etc.. To me as a mob novice theyre obscure names but im sure to guys in the know like pb, bronx, njcapo and so on theyre well known powerful guys and big earners... Love to know more about any of them foR my own curiosity perhaps on a separate thread , thanks fellas

toto marino, pete defeo, toto mirabeli, tommy lombardi,

nick rizzo..colombo guy

joe laforte

carlos marcello.tom gambino..what is he 88 , 5 years in the can .surrounded by millions

Charles Nicoletti, who was involved in numerous murders and schemes, stayed on the streets from 1944 untill his death in 1977. And as mickey2 said Accardo was the one with THE longest run on the street

With all these names popping up here, it's amazing how gotti got most of the country thinking he's a legend. What did he really have as boss? 4 or 5 years free on the streets, if that...

You do have to take into account the time period. Being a boss in the 40s or 50s was quite different than being one in the 80s or 90s. It's why Gigante's 16 year run on the streets as boss (1981-1997) was so extraordinary. Of course he had to go to extraordinary lengths to pull it off.

Yeah I didn't mention it in the post but I wanted to hear about people active in the 80s or even 90s. When things were still crazy with the violence but after the bulk of their connections started to fade.

Bulger was on the streets from 1965 until he went on the run in 1995, of course the FBI enabled this run to an extent.

Like others have mentioned Carlo Gambino and Trafficante sr never went to prison for anything. Tony Accardo is another who never did time.

jack tocco ran the detroit mafia for 35 years and spent 18months in prison from the late 70s to 2013. He was supposed to get 20 years when he was convicted in the gametax bust but he only got 18 months there is suspicious of foul play in the sentencing of jack tocco.

Had a very profitable run only real beef he had was later on in life with tony zerlli. I think tony always felt annoyed that he did not get the boss postition back in 1979 tonys father had been one of the most powerful bosses ever and tony himself served as acting boss in the mid 70s before going to prison while tony was away jack took over. Tony died broke in florida after he was shelved in the 2000s and his top associate jermome the blade was killed in 2002. Tony was allegedly very bitter and because of that tried to help the feds in finding hoffas body he was also threatening to make a website naming and shaming mobsters for money. There is even rumerous that jack wanted tony z whacked funny how two best friends can start to hate each other as time went on i think the gametax bust was the breaking point

Black Jack Tocco is quite possibly the most underrated mob boss of all time imo.

He ran this thing like it was supposed to be done. Just doesn't get the same praise as others because it's not one of the "Big 5" families

The few authors that have covered Tocco have given him credit. Scott, obviously. Also William Kleinknecht in his book The New Ethnic Mobs, which came out shortly before the GamTax case.

But running a small family in the Midwest that's into little else beyond bookmaking is a different story than running on the NY families.

Jack tocco is defo one of the most sucsessful bosses in the last 40 years maybe one of the most sucessful ever. The detroit mob true is mainly a gambling and loansharking operation. But it is still very big in legit business and those wiretaps in the game tax indictment showed extortion but you are right detroit cant be compared to new york but he does deserved credit.

jack being the boss kept it alive if tony z or the gicanclone brothers had been made boss the detroit mob would have died years ago gicanancole brothers were too flashy and tony z could not stay out of prison and was not the smarest guy.

Still i always wonder tony z came up in the 50s and 60s served as acting boss when detroit had real union power in the 70s as underboss in the 80s and 90s never thought at his death in 2014 he would be broke in florida hated by his crime family that bears his name and friendless i know he spoke to scott at the end of his life. jack died a multi millionaire but jack invested in legit tony did not enough and he had no income coming in. He went broke after those rico trials in the 90s and after jerome the blade got whacked all income he had disappeared.

i always wonder why jack did not whack tony z i guess shelving him was easier than killing him less heat and shelving tony was worse than death and there was no one loyal to tony after he got out esp after jerome was whacked and that old guy died of cancer(forgot his name) jerome was running his shy

What they may or may not be into now is not the same as back in Tocco's heyday

I doubt they were barely involved in anything besides bookmaking back then. Hoffa ring a bell? Hmmm unions maybe? But I digress...dont want to get thrown off track here

Hoffa was long dead by the time Tocco became boss. I'm not sure about the 1980's but by the 1990's the family's operations were mainly gambling (bookmaking, high-stakes card games), loansharking, and extorting unaffiliated gambling operations.

All time no doubt it's Tony Accardo. He started with the Capone Gang in the 1920's and ran the Outfit after Ricca went to prison in 1943 and still had an administration role in the Outfit until the 1980's. He was a top Outfit guy for over 40 years and never spent a night behind bars while guys like Ricca, Giancana, and Aiuppa were locked up.

The Genovese also had plenty of top guys who had long runs. Jimmy Alo, Jerry Catena, and Benny Squint all flew under the radar as top guys in the family.