Whitey Bulger, Jai Alai, the Winter Hill Gang, & the Tycoon Murder that Stunned America
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May 27th, 1981, and it's a lazy Wednesday afternoon at the Southern Hills Golf Club, an exclusive course just outside Tulsa, Oklahoma, and 55-year-old tycoon Roger Wheeler has just finished his weekly round. It's hot, a good time for a 19th hole beer, but Wheeler won't even make it out of the parking lot. Sat a few yards away is a Pontiac with four men inside, none of them is dressed for golf.

As Wheeler climbs into his vehicle's driving seat, one man steps out of the Pontiac and walks towards him. He's wearing a beard and sunglasses and looks, somebody remarked later, a bit like Kenny Rogers, only quote, dark complexion with hair over his ears and a full beard, his black hair streaked with grey. In the cowboy's hand is a .38 police special revolver and he's heading for Wheeler.

The gunman's stride quickens as he reaches the businessman's offside window, then bang, a single slug smashes through the glass and hits Wheeler right between his eyes, killing him instantly. The shooter then drops four unspent bullets as he sprints back to the Pontiac and his three accomplices, who speed away from the southern hills in seconds.

The four rounds aren't a slip-up, they're a warning. To anybody else who's thinking of following Roger Wheeler into the lucrative world of Highlight, a strange, ultra-fast, basque racquetball game that draws millions of dollars in gambling each year. At first, witnesses to the slaying are too scared to speak. They know damn well this is an underworld hit. Perhaps it's Italians who've been eyeing up Highlight long before Wheeler threw his fortune at it.

The beard, the sunglasses. The killer did kind of look Italian after all. Or maybe it's Boston's Irish mob, the Winterhill Gang, who'd be getting deep into the sport thanks to their connections with a former cop in cider and a gaggle of current and former FBI agents. Between them, they've created a kind of corrupt Swiss guard around their gang's leader, James Whitey Bulger, a balding Air Force vet whose thirst for blood has been growing of late.

Either way, Wheeler is dead, and America is shocked. Media swarm the southern hills, and authorities are talking about a new era in gang warfare. Eventually, the murder will bring cops, politicians, and some of New England's biggest gangsters crashing down. But not before many, many more people are dead, and higher life is consigned to graveyard locks on the SPN2. Welcome to the Underworld Podcast. ♪

Hey guys, welcome to another episode of the show where we teach you how all you need to swerve Boston's finest is a school friend and a Sancho Panza mustache. I'm Sean Williams. I'm finally in Berlin. My talented co-host Danny Gold is somewhere in the US. Are you on your magical mystery tour through the deep south yet? Or are you in Austin? Or where's your current location? I don't even know anymore, man. But I do know that gas is very expensive. So patreon.com slash the underworld podcast.

Also, we got mugs, t-shirts, hoodies, stickers, you know, everything like that at underworldpod.com slash merch. So check that out. Bang, straight with a hard sell. And we both chase monsters and bad guys around the world. And we do the same on this show, only with a far stronger weapon of journalism. That is, of course, podcasts. Any opinion you want to dish out about the Ukraine war from the US before we kick off?

Nah, just that I might head over there, I think, in mid-April. We'll see. All right. Okay, that's exciting. And yeah, a quick word from our sponsor. That's us. We've put up a bunch of stuff on the Patreon late. There was a Belizean blood gangbanger, Californian fraudster. We're going to have a new mini show out soon, Analysis. There's female narcos in Mexico and more stuff from my travels. And you're going to do a live blog of a night out in Asheville, right? So yeah, sign up to that. Price of a coffee a month. Yeah, you are. You are.

I mean, it kind of feels like ages since I did one of these. I think it's been like two or three weeks. So I'm going to start with a question, right? Who is your favorite Highlight player? And you can't say in the Aki Gojeka that quote Michael Jordan of Highlight because that is way too easy. Yeah, that was definitely going to be my answer. So I don't even have a second favorite. He just really takes the cake with all of it. But I actually thought Highlight was like Indonesian or something, like not Basque. So that's interesting.

Yeah. Your, your ignorance comes straight through there. I mean, I've just come straight off the back of reporting a stone throwing story. And this year I've done rugby in Sicily. That's available in your next issue of sports to the straight folks. And I'm going to do a dance piece later in the fall. I mean, I love niche sports and when you throw in a bunch of organized crimes, just like the best. So what is higher life before we get into all the organized crime that you guys are listening for the, to the show actually for, well,

Well, here's a description from journalist Howie Carr's book, The Brothers Bulger, which I've used a fair bit for this show. Quote, highlight is not a sport ever likely to be featured on ESPN.

It's a handball-like game played primarily by men from the Iberian Peninsula who have long curved wicker baskets strapped to their hands. I thought it was televised now. Like, I kind of feel like it was having a moment recently, but I could be wrong. I mean, I've watched, like, pro juggling on ESPN. So, yeah, I mean, I bet it is on TV. But Carl goes on, quote, like dog racing, it exists, despite what his fans may say, for one reason only, gambling.

played in arenas called frontons the sport has always been plagued by scandals yeah shout out to the revere revere beach uh revere in general the dog racing track there if we're gonna go full-on like trashy massachusetts or trashy boston right here yeah and shout out to my local one in crayford as well because that i like the dog race and i think it's great or is it abusive i don't know are we supposed to like it these days

I just know that it's like if you think horse racing is shady, like dog racing just is 10 times sleazier. And the dog racing track is probably 100 times sleazier than a horse racing track. I mean, it leaves the mask off. I prefer it to horse racing.

So the sport looks a little bit like racquetball, but it's played on the bigger, more open court. And instead of racquets, players carry these big curved baskets called cestas that they use to both catch the ball and hurl it back at the wall at speeds upwards of 180 miles per hour. So because of this, it's pretty dangerous, right? And the one, the fronton that is in Havana, Cuba, it's known as El Palacio de los Gritos or the House of Screams.

Jesus, that's an incredible name. But also, wasn't there like a jackass episode where they had a pro who was just like, I think he was wailing fruit at them from the little basket thing? Yeah. They were flinging oranges off their asses, I think. Oh.

It looked pretty, pretty great. Yeah. I love that. I don't think it was one of the movies. I think it was one of the episodes, but it was, it was terrific. That was my introduction to high lie. There you go. It's, it's, uh, it's not as good as this, but it's, it's a start. And yeah, I mean, I think this game is the fastest ball game in the world. I may be wrong either way. It's pretty nuts.

I don't think it's the most thrilling thing to watch. Apologies to our Hialeah-loving listeners. And more particularly than Iberian, it's Basque, which is this small region, northern Spain, southern France, come to Bilbao, San Sebastian, and other lovely places. It's popular in some former Spanish colonies like Mexico, Cuba, and the Philippines. But the fact you can bet on it, and people bet on Hialeah a lot, means it takes off in America at the turn of the 20th century. Wait, does it really? I mean, that doesn't...

Okay. Yeah, sure. I'll go with it. I have no idea. Let's just, for the sake of this episode, say that it's the biggest sport. And the first U.S. Fronton is built for the St. Louis World's Fair in 1904. But thanks to the large Hispanic population, the 1926 Miami Fronton becomes its biggest by far, the so-called Yankee Stadium of Highlight. I mean, what isn't called the Yankee Stadium or something?

The gambling brings punters from all over America, but in Miami, highlight is king. And some matches bring 10,000 people to its front on, which is pretty massive considering it's like a squash court. And of course, casinos are then bolted onto the venues and highlights to betting then what boxing is, I guess, to betting today.

Says Benny Bueno, a former highlight player and owner of the best name ever to NBC, quote, we wouldn't get, you know, five or 6,000 people in a performance. And in the early eighties, there was a couple of exotic wages that really brought the big gamblers out. And one day it wasn't odd to see a million dollars bet in one day. I mean, this is big money stuff, right? But this show has whitey boulder in the title. So let's back up a little bit. And before that,

Yeah, I know. This is part of the plot for the 2015 movie Black Mass, which stars Johnny Depp as a badly dressed, crack-eyed wife beater. I guess the role he was born to play. And actually, Black Mass isn't too far off the truth, although it kind of buries the lead because the highlight stuff really should have been the story alone. Compared to American Gangster, it's essentially gospel. I'm going to rate it like 8 out of 10 on the Truth-O-Meter.

I don't even remember that part of the movie or the movie in general, but I guess I don't remember much these days anyway. Yeah. I may have got the idea from this show by watching it on a recent plane journey. Um, and I probably cried to black mass, like a cry on every single play, play movie, but, um, that's a thing. I feel like that's a, that's a thing that happens or something. And it makes you cry. I don't know. It's something, something scientific, but like I, you know, I'll, I'll get down with some tears on an airplane movie as well. Yeah. It could just be deep sea depression, but,

Anyway, we'll do a more in-depth episode about Whitey Bulger and the Boston Irish mob at some point. So I won't go too far into his backstory here, but here's a quick rundown of his life and crimes. Whitey's born in Boston in 1929, and he serves in the Air Force between 1948 and 1952.

Four years later, he's convicted of hijacking and he lands in Alcatraz, among other institutions. While he's there, he negotiates a smaller sentence in return for participation in a CIA scheme to dose up prisoners with acid. So that's fun. Bolger gets out and he commits his first murder in 1965 and he shoots dead the twin brother of a gangster his Irish mob are at war with.

They'd actually make for a great episode too, I think. Especially like the Rhode Island. I think it was two factions, but the Rhode Island faction, which would get into like Buddy Cianci and stuff. But I guess Crime Town already did that in their own way.

Yeah, there's a few interesting characters that pop up in this show. So I reckon we could go back and plumb that at some point. But at this same time, amazingly, Whitey's brother, Billy, who's played by Jamba Wach Bumba Stinker, whatever his name is, in Black Mass, he's rising the rank of politics and becomes the longest president in the history of the Massachusetts Senate.

So in 1978, the year Billy first wins that role, Whitey is actually top of the pile in Boston's underworld. And he makes his biggest earnings fixing horse races. But Highlight is just right there. And it's making tons of money, gambling money. And what do mobsters like more than some weird sport nobody watches that's part owned by casinos and raking in a bunch of cash?

And what's more, by 1976, authorities have demanded that the president of World Higher Lie, that's the biggest organizer, steps down over shock, gambling irregularities. Two years after that, so in 1978, Roger Wheeler steps in.

He's the former owner of TelexCorp, a leading maker of computer processing tech. And by most accounts, your typical 20th century corporate raider kind of guy. Here's a New York Times obituary in 1981. Quote, he was a classic entrepreneur, tenacious and aggressive. He drove himself and others to the limit in building an eclectic business empire composed of six companies at his death.

Roger liked the feeling of making a buck. He was a driven and demanding man, one friend said. That allowed him to do a tremendous amount. And fuck that guy. Yeah, fuck that guy. I agree. In 1978, Wheeler buys a holding firm for World Hireline Miami, but it's not all smooth sailing.

He's brought before the Connecticut Gaming Policy Ball for an alleged high-line hookup with Maya Lansky, the so-called mob accountant and one of the leading figures in the American underworld. Interestingly enough, I'm working on an episode on Murder, Inc., which he figures, you know, not prominently, but he's a decent part of it. And kind of, you know, the mob accountant thing is kind of like not really an accurate description.

from what he actually was and what he did. But we'll get into that, I think, in the episode. Oh, cool. Yeah, it's going to be a good episode. Myolansky is one of those figures that's kind of passed me by a little bit over the years. I want to know more. But according to associates... One of the few to die of old age, man. Man.

Man, okay, well that's pretty impressive. We're not going to get any of those in this episode. According to associates, Wheeler's interest in highlight is purely business. And surprisingly, he shares about as much passion for historic Basque village sport where guys in polo shirts ping a rubber ball off a giant squash court with banana-shaped baskets as you do, Danny. But according to Howard Carr's book,

One of the main reasons Wheeler gets involved with World Higher Light at all is the involvement of an ex-FBI officer named Harold Paul Rico. This guy is interesting. He joined the FBI in 1950 and he becomes one of the Bureau's most prominent recruiters of informants in the 1960s Boston underworld.

His most famous turn is to get mob hitman Joseph the Animal Barboza to testify against his bosses. That's one of the leading Italian mobsters at the time. And Rico's also known for having groomed Stephen Fleming,

Now, Flemmy is a young crook who is, by the 1970s, one of Whitey Bulge's closest capos, a real violent man who gets the nickname the Rifleman for his willingness to shoot first and ask questions. Well, I mean, he never asked questions.

Having Rico, who's this prominent ex-cop in the organization, that's World Highlight, with almost 20 years on the force, who's developed a fearsome reputation for turning and convicting underworld monsters, well, that puts Wheeler's mind at ease about throwing money at a sport that's wound up with gangsters. He throws 50 million bucks into World Highlight, which is turning a tiny annual profit of 6 million. It's a no-brainer.

Now, World Highly has been owned by Bostonians going back to the 1920s, and it owns Frontons, those are the highly arenas, in Tampa, Miami, and more recently, one in Hartford, Connecticut.

It's a world high lie. It's like the UFC. It's like the league or something of this sport. I was going to say, the UFC is a really good analogy because there's like three or four major ones, and this is the one that basically everyone bets on. So yeah, you know, there's WCW, but this is the big boy. Bulger is first brought into the sports fold by a fat accountant named John Callahan. Sorry, John. I've just like teed you up as a fat accountant. According to one Boston reporter,

private detective this guy has quote a bad case of gangsteritis he likes hanging out with rungans basically callahan briefly attended yale in order to learn chinese he graduated with a degree in accounting from bentley college and he began working in his father's wholesale produce company in charlestown massachusetts which at that time at least as many irish monsters as south boston

A Callaghan is even at one point the housemate of Johnny Martirano in Boston, who winds up being one of Whitey Bulge's most trusted trigger men. I mean, Callaghan is knee deep in the gang world. And once the original owners of World High Alive pick him up, he gets to work embedding his mobbed up powers in the sport.

First, he gets age-poor Rico in, who starts chatting up old bureau colleagues and taking them on trips to the Bahamas, which isn't suspect at all. And why you Bulger? He's soon making a packet off the game, skimming and providing protection around 50,000 bucks a week in today's cash. That makes Hirelight his biggest single earner before the Winter Hill gang picks up on the cocaine craze of the 80s.

Mostly it's parking revenues the Gans are skimming from, which is kind of genius, right? Because it keeps the distance from the sport and the betting itself. Whelan keeps Callaghan on at world highlight when he puts his money in. But he's no mug. He knows his deputies bedfellows. Yeah. Says the half-incurrent newspaper...

Wait, current. At the time, quote, The article goes on, quote,

Wheeler spoke continually with Connecticut State Police detectives. He recorded his telephone calls and trained his staff in stress analysis so they could review the recordings and speculate about who was lying to him. Well, that's kind of wild. I wonder, like, I really wonder if that actually works. Yeah, I mean, is that just, like, lying detectors, or is that kind of weird? I don't know. I think it's...

More like informal, you know, it sounds like like not a probably just like analyzing the words and the way they breathe. And I don't know something along those lines, but some kind of probably is right. Scientific. Yeah. Yeah. But no, he's recording phone calls. So I don't know. It's interesting. That's all. Thank you. He became so concerned for his safety that he once had his pilot take his private jet up for a spin around the airport in Tulsa before he boarded a flight to Connecticut.

I mean, your life's really going downhill when you have to get your private pilot to take a private jet like that. Here's an excerpt from the book One Murder Too Many. Quote, although Wheeler was reluctant to give interviews about his higher line interests, in 1979, he wisecracked to a Miami Herald reporter. He brushed off, I have enough golf buddies.

Hey.

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When briefly interviewed by a Miami reporter in 1980, he expressed fear that a lengthier interview might expose him to kidnapping and asked that the reporter note in his story that he employed several former FBI agents. And it goes on. While being vetted for a WJA, that's World Highline, front on in Connecticut, Wheeler asked a state investigator...

Are these people I'm involved in, are they reputable people? The investigator, D'Antuomi, was surprised by the question. You didn't buy into a church, you bought into a gambling facility. If bad guys can buy into a facility, they will. Despite this, shortly before his death, Wheeler told someone that the New York Stock Exchange was a greater gamble than higher life. So Wheeler then launches an in-depth audit of the group's finances, looking for where the skim is, right?

And first, he approaches a young cashier named Peggy Westcote, who lives in a small home in Dade County. Does she know what's going on in Hartford? He asked her. Well, that is a fatal move. Callaghan gets word of his boss's inquiry and he passes it on to Bolger. In December 1980, two men break into Westcote's home and hang her boyfriend near the front door. Then they grab Peggy,

I mean, that garbage disposal thing, that's inventive and just brutal. It's horrific. Kind of unnecessary. Yeah, it's horrible.

When Wheeler gets word of the double slaying in Dade County, he realizes that his newest possession is Riddle with Mafiosi, and he makes plans to sell off World Highlight and remove the Connecticut connection. Now he realizes it, right? Yeah, yeah. I think it's taken him a little while, but he's getting there. And for the Winterhill gang, right, this is just not going to do. So Bolger plots to have Wheeler himself killed.

But Bolger, he makes a really weird decision. Rather than go for one of his trusted gunmen for the wheeler hit, like Flemmy or Martirano, he reaches out to this Florida guy called Brian Halloran. That's the guy played by his PSRs guard in Black Mass. Halloran is a drunk, and he's a coke fiend. And he's even screwed up before. He messed up a loan connection, and that led to the incarceration of Johnny Martirano's brother Jimmy in 1974.

What's more, Hallorann's own brother is a state cop and he's connected to older Winterhill mobsters Bolger has long gone against.

According to Howie Carr's book, it's only Callaghan's say-so that persuades Bolger that Halloran is the guy for the wheeler jobs. That's Halloran, Callaghan, Bolger. Sorry, guys. But the plan falls through when Whitey Bolger finds out that Halloran has given a ride to Louis Littiff, and that's a bookmaker who'd been murdering without Whitey's consent and whom Whitey himself had shot dead earlier in 1980.

Halloran is a potential witness to a Winter Hill murder and a muck-up to boot.

The crew sends Halloran packing before placing 20 grand in his car a few weeks later. Quote, we shouldn't have got you involved to begin with, Callahan, tells Halloran, who rather than stash his earnings and disappear, buys a new whip and just goes on a bender in Fort Lauderdale. Great place to go on a bender right there, Fort Lauderdale. I've driven through it, it looked seedy as, yeah, maybe one day. That is, by the way...

So that bender in Fort Lauderdale, that is also a pretty bad idea. But for now, coked up Halloran is off on his own, enjoying his newfound windfall. For now, the Winter Hill sights are set firmly on Roger Wheeler.

It's Rico, the former FBI agent's intel that lets Whitey know that Wheeler, a creature of habit, is often to be found at the Southern Hills Country Club in Tulsa. That's this super exclusive place founded weirdly during the Great Depression and also weirdly is just about to host the PGA Championship this May. Is that like how exclusive can something be if it's in Oklahoma? I'm going to take that as a great offense on behalf of my former friends.

I mean, because it's the South, it's kind of even more exclusive, right? Because it's got all that fun past. But anyway, this time the Winterhill boys are taking absolutely no chances. They call in fugitive killer Stevie Flemmy, one of Whitey's closest confidants and he's linked to the Boston Mafia, the Patriarcha family, to do the dirty.

Flemmy is portrayed in Black Mass, the movie, as this conscience-wracked gangster who flinches at the worst episodes of violence. And if I recall, he even gets the emotional final word in the movie. But in real life, he's a convicted paedophile and prolific murderer. For what it's worth, Flemmy will later point away at your trial and say, quote, you want to talk about paedophilia? Right over at that table. So just, you've got paedophiles flinging axios at each other. It's just nice, guys.

Anyways. Yeah. Anyway, Flemmy and a couple of others fly to Tulsa and case out the Southern Hills. Whitey sends a bunch of untraceable 38 police special revolvers. Days later, Wheeler is dead at the wheel of his car.

Now, you might think that, you know, a killing in broad daylight, there'd be plenty of witnesses. Well, actually, there are. But fortunately for the Winterhill gang, they're all black workers at the golf club and none of them much fancy getting involved in a gangland hit to bring justice to a robber baron. Says the Tulsa FBI office, quote, they are black, uncooperative and do not want to become involved in rich, quote, white man's affairs.

That's just, that's an amazing FBI quote right there. It's pretty amazing. Yeah. And next after Wheeler, now it is Halloran's turn. In the fall of 1981, somebody fires a shot at his apartment in Quincy near Tallahassee.

By this point, Halloran's a full-blown junkie, and a few weeks later at a Chinatown restaurant, he shoots a dead drug dealer named George Pappas while they're with a guy called Jackie Salem, who's a key figure in Boston's Italian mafia. That's the Patriarcha family. But wait, he wanted a Halloran dead just to wrap up like loose ends? Yeah, exactly. And Halloran, by this time, has just gone off the rails. This murder kind of proves the point. And then he's definitely in with the Italian mafia, why he's kind of like...

got this simmering conflict with. So he's not, he's not really going to be around for too much longer. Um,

So this killing, right, this killing of the drug dealer George Pappas, this gives Whitey a great chance to off Halloran and blame it on the Italians. And Halloran knows it. He turns himself in to the Boston police, but they won't protect him, writes one officer, quote, source advised that the mafia want Brian Halloran hit in the head to shut him up as a potential witness. Halloran is not even the next person on the Winter Hill High Line chopping block.

In September 1981, Steve Flemmy brings his girlfriend Debbie Davis to the Flemmy home in Boston. She's been dating other guys, including a Mexican who's already been shot dead. She knows too much about the Winter Hills many scams. As she enters the home, Whitey strangles her in front of Stevie. This bit is pretty truly portrayed in the movie, aside from a fictional stint in jail for Davis.

Then Whitey's men strip her, cut off her fingers and toes and dump her in a nearby Neponset River. Says Kevin Weeks, a young Winter Hill gang enforcer portrayed in Black Mask by Jesse Plemons, quote, I go and use the bathroom upstairs. And as soon as I come down the stairs, I see Stevie and Deborah come in and I hear boom, boom. I walk in and see that Jimmy had strangled her.

I thought that she was dead, but then Stevie put his head on her chest, said she was still alive, and he put a clothesline rope around her neck, put a stick in it and twisted. And then after, Stevie dragged her body downstairs and pulled her teeth out. So Stevie wasn't at all sympathetic, mourning and sorrowful like he is in the movie. Stevie enjoyed murder.

And I mean, yeah, sure, Kevin, you went upstairs and you didn't see anything until it was all over. But, you know, it kind of paints a picture of what these guys were like. Pretty, pretty disgusting. Now, as shown in Black Mass, Whitey Bulger is a major FBI asset and he uses his informant to get rid of Hallorann.

Whitey tells agents that the Italians want Halloran dead across multiple meetings, and the Bureau incredibly cuts Halloran loose, believing Whitey's information, and second, that Halloran is a mooch and a fantasist. Now, that decision by the FBI is going to cause tons of problems for them further down the line, and that's going to bring in the story of John Connolly, who's one of the main protagonists of the movie Black Mass, and he's played by Joel Egerton-Morris.

That's going to come later on in Whitey's story. But for now, for Halloran, unsurprisingly, all of this is a death sentence. On May 11th, 1982, a young gangster comes around Whitey's knockoff appliance store in Boston, one of his many rackets, and tells him he's seen Brian Halloran drinking at a bar called The Pier.

immediately whitey springs into action he gathers men at one of their clubs and he jumps in quote the blue chevy that's a souped up sports car with some hit enabling james bond-esque add-ons one button for example sends smoke billowing everywhere while another dumps fuel onto the street sending pursuers skidding all over the place fucking mario kart over here man

Why he even dons a disguise. He throws on a brown wig and a moustache to make him look like Jimmy Flynn, who's another Winter Hill guy with whom Hallorann's been fighting, or I guess Mario. Soon after, Hallorann leaves the pier with a casual friend called Michael Donoghue, who's offered him a ride home. The blue Chevy pulls up alongside their car and fires an automatic carbine rifle into it, killing Donoghue, whose car drifts across the lot and smashes into a building across the street.

When cops arrive minutes later, Halloran is alive. Just. Who shot you? The cops ask him. Jimmy Flynn, Halloran replies. Then he dies. By this time, the press has gotten wind that Halloran and John Callaghan, who, by the way, is still leading world hire life, have been close friends all that time, and that Callaghan would soon be questioned by cops about who killed Roger Wheeler.

Incredibly, Whitey foods bullshit to his handlers again to send them off the trail, helped by a couple of bent cops who fabricate leads to keep their colleagues away from the big man himself. Whitey tells the FBI that Callaghan has been getting worried about a bunch of Cubans with Highlight and he's meeting with them in Fort Lauderdale.

Only Callaghan is actually fine to Fort Lauderdale for what he thinks is a routine visit with his pals, Johnny Martirano and Joe McDonald, another mafiosi. They force him into a van. Cops find Callaghan's body later in a silver Cadillac at Miami International Airport. Two gunshots to his head and a dime on his chest. He's missing a ring.

Moments later, the police get an anonymous tip about a ring found in a trash can in Miami's Little Havana, sending them on a wild goose chase after Cuban gangsters they really, really hope have done the deed. Of course, they get nowhere, and the true killers scram. They've got tons of moles in the mob, and the guys who aren't paid off are acting just like side characters in a GTA game, proper clown car stuff by the boys in blue. Anyway...

As an interesting aside, I think the movie Black Mask kind of lets the FBI off the hook. It pins everything on John Connolly and John Morris, two cops who form a close allegiance with Whitey. But in reality, there's this whole massive supporting cast of turned cops and officers, I mean, not least H. Paul Rico, who helped Whitey slip off the hook for decades.

Says Kevin Weeks that Winter Hill gang enforcer, played by Jesse Plemons again, quote, the FBI were the ones that enabled Stevie and Jimmy to survive. And survive? They do, but not forever. After the Highline murders, Whitey Bulger descends into ever deeper circles of crime, trafficking huge amounts of drugs and even supplying weapons to the IRA, which is locked in urban warfare against the occupying British army.

In 1994, convinced that the FBI are aiding Whitey and the Winter Hill guys, the DEA launches a full-scale operation. John Connolly helps his underworld contact out one last time and Whitey goes on the run for 16 years.

Connolly, of course, gets locked up for that and other assistance he's given Whitey over the years. Meanwhile, Steve Flemmy and Johnny Martirano, his lieutenants, are basically just backpacking around Europe. According to the younger enforcer, Weeks again, quote, Jimmy and Stevie were travelling on the French and Italian Riviera.

The two of them travelled all over Europe, sometimes separating for a while. Sometimes they took girls, sometimes just the two of them went. They would rent cars and travel all through Europe. Sounds quite nice. But Steve and Johnny's bromance doesn't last long. They're brought down in 1995 alongside two other mobsters in this huge bureau operation. Flemmy gets life sentences in Florida and Oklahoma courts for murder.

Martirano gets charged with racketeering. But in 99, he turns state's witness and he confesses to over 20 underworld slayings, including Roger Wheeler and John Callaghan. As part of this deal, he gets just 12 years in jail. That's like seven months per murder, which is pretty incredible lawyering there, Johnny. And he was actually let out in 2007. What? I mean, who did he give up in this deal? Jesus. Yeah, I mean, everyone, but still, that is unbelievable.

So next up for the Bureau is H. Paul Rico. Remember him? That's the 20-year mafia-busting FBI agent who crossed over to the dark side and helped Whitey Bulger eliminate anybody in his path to high-life riches. In 2003, Oklahoma and Florida authorities arrest Rico in connection with Roger Wheeler's death, part of a sprawling plan to root out the bent cops who'd let all this madness happen in the first place.

Now, there's already something that's sticking in the cops' craw, and that is that Rico has allowed a mafia member named Joseph Salvati to be framed and spend over 30 years in prison for a murder they know he never committed. And when questioned about that case, Rico says in court, quote, what do you want, tears?

But Rico died in 2003 while under indictment for the Wheeler murder, and he never faces justice. Says a lawyer involved in Rico's case to the Boston Globe, quote, Mr. Rico takes with him many unanswered questions to his grave. But more importantly, the information he had could have shed light on many others who were involved in his wrongdoing over many years with the FBI.

Cops also lose track of Whitey Bolger for years. The only credible sighting of him since heading out on the lam is in 2002 in London. But in 2011, he's captured in Santa Monica aged 81. And in 2013, a South Boston court finds him guilty on murder, racketeering and illegal firearms possession charges. Whitey gets two life terms for his crimes, but he doesn't even make it five years before he's murdered in prison, people beating him to death while he's in a wheelchair.

I imagine for being a snitch, right? Yeah, and just for being Whitey Balder. I mean, he's turned on everyone over the course of his life. Investigations into that particular murder are shockingly still going on. Two inmates spent almost three years in solitary for it, but nobody's been charged.

Here's a great piece by Michel McPhee at LAMAC, quote, James Whitey Bulger was 89, incontinent, and so frail he was confined to a wheelchair on that late October day in 2018. When the Federal Bureau of Prisons abruptly changed his classification, moved him to U.S. Penitentiary Hazleton in Preston County, West Virginia, and...

for the first time since his conviction on 11 counts of murder and other racketeering charges connected to his reign in Boston as both a crime boss and a secret FBI informant put him in general population, where a cabal of his enemies from Boston were waiting. Yeah, so sounds like a setup pretty clearly. It's pretty, pretty sus. McPhee goes on, quote, four hours after his arrival, Bolger was dead.

I bet, I mean, I'm guessing that's the informant side. Yeah.

His body is now buried in a Boston cemetery alongside his parents under a gravestone etched with a simple cross under the name Bulger. Sweet dreams, listeners. Whether the feds were unaware they were putting on a geriatric killer and cop informant into a prison with tons of guys he'd screwed over, well, I'll leave that thought to John Gotti Jr., son of the Gambino crime boss. Quote, you'd have to believe James Coney farts unicorns to believe that line of shit.

Yeah, I kind of feel like those younger second generation, third generation guys just aren't the same with the pros as the older ones were. Yeah, I mean, you can tell they went to liberal arts colleges right on their dad's money. But of course, there is, of course, a brutal medieval justice to all this, but...

We really don't know the full extent of Whitey Bulger's crimes, which reached amazing levels of cruelty. Talking to the Daily Beast after the Black Mass movie comes out in 2015, Kevin Weeks, that low-level enforcer, he also details a plot to kill Harry Carr, the author of the two Bulgers book, and now, sadly, has become some conservative shock jock. Says Weeks, quote, "...one FBI agent actually gave us 17 kilos of C4."

with which we were going to blow up a reporter, Howie Carr. Howie thought it was a made-up story until he found out it was the truth. Carr wrote an article about this kid in South Boston who got killed, and Jimmy decided to make him a hobby and shut him up once and for all. When I look back on him, I wish we did kill him. He's still the most hated reporter in Boston. Everybody hates him.

17 pounds of C4 sounds like the kind of thing you could take out multiple apartment complexes. But also this guy, Harry Carr, that's the book you based a lot of this off of, right? Yeah, he's like a super famous reporter in Boston and written over a dozen books, I think. Does everybody hate him? I mean, I hate him these days. He's a complete dickhead. But I don't think I'd get 17 kilos of C4 off the FBI to kill him. I'm not a violent gangster yet.

What is almost as stunning as all of this death and destruction is that for decades, while his brother Jimmy is becoming one of America's most violent, gruesome mobsters, Billy Bulger's star just keeps on rising. It's only in 2003, when he's hauled into a congressional hearing about how his brother invaded the law for so long, does his star begin to fall.

Billy refuses to sully his brother's name and it costs him his prestigious tenure as president of the university of Massachusetts, which is his cushy old man job. Yeah. It's pretty unreal. Yes. It's mad. Says the New York times piece in 2013, when feds finally send Whitey down, quote,

It was this silence that cost William, that's Billy, Bolger, his university position 10 years ago and deepened suspicions that he knew more about his brother's exploits than he let on. No shit. After all, William lived right next door to a house owned by one of Whitey's partners in crime where the gang hatched plots, stored of arsenal and weapons and even committed murder. I don't try to sort it out any longer, said Billy. I just try to be a brother.

John Connolly, the corrupt FBI agent who'd helped Whitey off the hook for years, now has terminal cancer aged 80. A Florida prison review agreed to release him on compassionate grounds last year. So, you know, I guess some people do dial. I can hear you all asking, what happened to Hireline? Well, I've got pretty bad news or good news. I don't know. The Wheeler case rocks its world.

And throughout the 1980s, Highline's popularity for players, viewers and gamblers, it plummets. That decade, its leading players conduct a three-year strike, the longest in pro sports history, which I assume will soon be broken by every football team in Russia. Last December, the last front-end at the casino at Dania Beach, Florida, closed, prompting fears that the game's days in the state are over.

There are some trying to revive it, although if I told you the most recent high-profile ones are at Miami's Magic City Casino in Tijuana, Mexico, would you believe that it's shaking its crime-ridden past? Magic City's Scott Savin told Miami 7 News this month that, quote, if this fails, there will be no professional highlight in the United States. So it's sort of an all-hands-on-deck.

Why the gambling thing? Is it just like a really easy sport to fix? I mean, I just don't. Why did gambling go? I assume that that was the case, right? Because it's just people playing squash with baskets on their hands. So I guess you can just fling it slightly above or below a line and get more points or less points. I mean, I don't know. Someone's going to have to email us and let us know why this thing is so bent. But yeah, it's screwed up.

So Mr. Savin at the casino, he is joined by former you, former university of Miami and NFL player to Nard Davis quote, we control the destiny of where highlight goes. If you ask anybody, would you want to be the last survivor of a sport where it has so much tradition? Yes. Or, or here's an idea to Nard, maybe no, you know, that's, that's highlight for you folks. And, uh,

Yeah, that kind of brings this episode to a close. Lots of pretty horrible stuff going on, but I hope you will watch ESPN 2 or 3 or 4 or 9 or whatever highlights on these days. Wait, so is that like recent right now? Like they're kind of figuring out what to do with it or is that from an article from a while ago? No, this article was from like two weeks ago. So people are really trying to get back on it. Staying current.

Yeah, right. Yeah, well, I mean, good luck. I mean, I'm definitely interested now. Maybe if it was on ESPN 12, maybe I'd watch it. So good luck to them. Then you won't again. But yeah, thanks for tuning in, everyone. Patreon.com slash underworldpodcast. Give us money so we keep doing this because otherwise I don't even know. Anyway, thank you all. And until next week. Shopify's already taken the cash register online, helping millions sell billions around the world.

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