Inside Track: An Oral History of Boston Gossip

For more than 25 years, the Boston Herald’s Inside Track struck fear into the hearts of the city’s boldface names and delighted eager readers. Now it’s dead and gone. An oral history of the rise and fall of Boston’s most loathed (and loved) gossip column.

Illustration by Ben Purvis; photos via Getty Images

There was a time, not so long ago, when Bostonians could sit down with their Dunks, flip open the Herald, and feast on the Inside Track’s salacious, behind-the-scenes scuttlebutt about the city’s glitziest and most notorious figures. Bloopers and blunders, scandal and intrigue—shenanigans served up with delicious headlines and mouth-watering pics.

It was a moment in time. Twenty-eight years, really. Nearly 15 more when you add Norma Nathan, whose pioneering gossip column The Eye—which ran from 1977 to 1991—set the table for the Inside Track’s run from 1992 until 2020.

At the height of gossip’s glory days in Boston, Gayle Fee and Laura Raposa—the so-called “Track Gals”—dished on everything from Patriots quarterback Drew Bledsoe’s swan dive at the Paradise to Michael Kennedy schtupping the babysitter. Pols, business titans, the glitterati, home-grown celebs—no one was safe. Names were named. Secrets spilled. Their column made blue blood boil, struck fear into those who were caught red-handed, and riveted readers with every black-and-white published word.

Fast-forward to today and, well, the party is officially over. And we are in mourning. This is the story of the rise and fall of Boston’s local gossip scene—as recounted by the Inside Track’s hilariously sharp-tongued scribes, their hard-working editors, their shadowy sources, and their bold-name targets.

In the beginning…

Long before the Inside Track became the most titillating read in town, Boston got its first scandal sheet in 1977 thanks to Norma Nathan, who showed little mercy for her prey in a Boston Herald column called The Eye.

Jonathan Soroff, Improper Bostonian social columnist, 1992 to 2019, and current Boston contributing editor. The definition of gossip in Boston has always been very different. The powers that be were like, We don’t talk. Omertà, the code of silence for organized crime, has always existed here for society. Norma Nathan was the first one, the ultimate gossip columnist in this city. She was a boomslang, like a spitting fucking cobra. Mean-spirited as hell. She never let the facts get in the way. And the damage she caused and the ill will that she spread—it was evil.

Charles Laquidara, radio DJ, WBCN, 1968 to 1996; WZLX, 1996 to 2000: She was the most popular feature in the paper. Everybody wanted to read what she had to say.

Ken Chandler, Boston Herald Editor in Chief, 1986 to 1993; Herald Media Editorial Director, 2004 to 2006: I would say that she definitely bore grudges. I think a lot of people were quite grateful they were not in Norma’s column. She was an absolute terror; she terrorized everybody.

Peggy Rose, Publicist: I had a great relationship with Norma. I was in my twenties and doing PR at the Hard Rock Café. She invited me to her home up in Middleton for lunch. I ran over her puppy and killed it. I thought my career was over before it started. People called me up and said, Why didn’t you run her over?

Mark Jurkowitz, former media critic, The Boston Phoenix and The Boston Globe: It was a very high-profile column. Many people couldn’t handle her. If your ox wasn’t being gored she could be funny. But she was pretty close to a New York–style gossip columnist, and she struck fear into the hearts of a lot of people. One day she said something, and that was it. We came up with the Error of Her Ways, a fact-checking column that we ran every week in the Phoenix to sort of torment her. Misspellings, how many basic facts she got right or wrong. It was pretty funny.

For a quarter of a century, Laura Raposa (left) and Gayle Fee (right) , a.k.a. the Track Gals, ruled the city’s gossip scene. Photo by Lynn McCann Youngen Photography

Soroff: I was there the night that she and [Boston Phoenix owner and publisher] Stephen Mindich got into it. They hated each other. It was literally this close to fists. She threw a drink in his face at the opening of some Lansdowne Street club.

Jurkowitz: She went up to Richard Gaines, then the editor of the Phoenix, at a Boston magazine party and threw a hot cup of coffee in his crotch.

Paul Barclay, former owner of the Comedy Connection and the Rack: I felt like Norma was a godmother to me. I had breakfast with her a few days a week. Everybody read The Eye. If you lived in Boston back then, it was like saying who is going to step in after Brady.

The Inside Track is Born

When Nathan passed away in 1991, Herald editor in chief Ken Chandler tapped Nathan’s former editor, Gayle Fee, and business reporter Laura Raposa to start the Inside Track the following year.

Laura Raposa, Inside Track Gal: Norma was the hardest-working woman in show business. She died of cancer. She had jaw cancer.

Gayle Fee, Inside Track Gal: We thought it was from gossiping. Can you imagine?

Raposa: God rest her soul.

Chandler: I started the Inside Track. Yes, I am the guilty person. I came to Boston from the New York Post, Page 6, so I knew what the power of gossip was, that it could be important for a paper like the Herald. Boston was a very media-savvy town, where people were well-informed and knew who the players were. If you were preparing a meal, all the ingredients for a great gossip column were there.

Raposa: God bless Ken! He was crazy, and I loved him. He knew the value of good gossip. He wanted us to write about everybody—sports figures, business people, politicians.

Fee: Cam Neely was on the Bruins and he was dating Glenn Close and best friends with Michael J. Fox. So our first column was Cam had Glenn Close in one box during a Bruins game, and another girl in another box.

Kevin Convey, Herald Reporter and editor, 1981 to 1987 and 1990 to 2007; editor in chief, 2007 to 2010: When the Inside Track started, Boston was a very buttoned-up town, and it was also a hard town to crack in terms of what was really going on behind the scenes. There was scandal and everyone was talking about it to each other, but nobody was reporting it. Because The Eye was run by a woman of a certain age, it didn’t take in the sweep of rock stars and young entrepreneurs and the younger set. Gayle and Laura had access to those circles in a way that Norma Nathan did not. Plus, the amount of stuff that you could report on expanded. Once the tech thing got revved up, people not only didn’t mind other people knowing they were wealthy and how they spent their money, they liked it. They welcomed Gayle and Laura into their circles, and they got stuff that nobody else in town was getting.

Fee: Princess Di was on the Vineyard at the same time that Bill Clinton was there. We happened to be friends with Clinton’s landlord, who happened to talk to the Secret Service, who happened to tell him where Princess Di was staying, and he happened to tell us. So we were the only ones who knew where she was staying and no one else could find her. We drove back and forth and back and forth in front of the house until finally there was a car pulling out. We followed the car to Vineyard Haven and Princess Di started shopping. She went in and returned two sweatshirts that she’d bought for her sons, which I promptly went in and bought. We were the only ones who found her the whole time, the only ones who got great pics of her, and the Brits were all hiding in the bushes and they all got poison ivy.

Raposa: You know who kept us going for years, until he didn’t? John Kennedy Jr.

Fee: We were the first ones to report that John was dating Carolyn [Bessette].

Raposa: Some people ran from us at parties. At the Democratic convention in New York in 1992, the Herald people kept sending me up to the buffet and the raw bar to get food because when I went up, it was like the parting of the sea: Hey, Laura, get me more shrimp!

Chandler: Laura and Gayle could be equally as terrorizing, but they had something that Norma didn’t have, and that was charm. They could get you to tell stuff that you really didn’t want to tell, but by the time the call was over you had told. Being a good gossip columnist, you have to have an edge, but you also can’t screw people. Gossip is a two-way street. So I think the Inside Track was great at getting information, but also had credibility and a large degree of trust.

Fee: We were the queens of taking people out to lunch. If you take somebody out to the Four Seasons, they feel obliged to tell you something.

Bruce Mittman, general manager of WAAF, 1990 to 2000; president of WFNX Radio Network, 2001 to 2003: Back in the ’90s, you didn’t have the Internet, you had activities—events or places where everyone met and connected. Laura and Gayle were at every event. That’s how you built contacts, relationships, credibility. The music scene, the clubs, who was there, who wasn’t, athletes that were there. It was a great time. It was fun. They could be controversial, but they were good people, good friends. They made life exciting. To be around them was to be around what was going on in Boston.

Fee: We got a phone message that Bill Belichick was sleeping with some guy’s wife in New Jersey and that he was named as the other man in the divorce papers, which we went to Jersey to get. We ran a pic of Belichick in his sweatshirt and he looks all grumpy and slobby and the headline was “Bill Stole My Wife.” I had that hanging up in my house; that was a good one. Or what about when Belichick brought his two girlfriends to the Super Bowl. He had the Jersey housewife whose husband sued him, and then he had his new girlfriend—his current one, Linda—and they were both at the Super Bowl.

Raposa: We knew all about the sports guys’ affairs. Never-ending. God bless ’em.

Barclay: In the early 2000s, a Red Sox pitcher had been to the Rack. He pitched Saturday, so chances are the next day he wouldn’t be pitching. He went out that night and went crazy, drank his brains out. He was there well after closing. Sure enough, he got called in to pitch Sunday and gave up like three runs in two innings. Blew the game. The next day I get a call from Laura and Gayle. If I admit it, then I’ve got the Red Sox furious with me, and if I deny it, then I’m going to get on their bad side. So there was that fine line to walk with those two. They wrote the story anyway on Tuesday: “Lowe Down Dirty Shame.”

Fee: We ran a story about Derek Lowe at Lucky’s after he got blown out by the Yankees. He was onstage singing “New York, New York” with Al Vega. We got a call the next day. Hi, this is Derek. Laura’s like, Derek Lowe? No, Derek’s friend Derek. [Laughs.] He’s like, We had an agreement with the bar that there would be no reporting. And Laura’s like, Well, Derek’s friend Derek, did you have an agreement with everyone in the bar?

Raposa: The stupidity of people. Derek’s friend Derek called back subsequently, too, to, like, dish on Derek. Men were the best sources. They’re like little old ladies gossiping. Practically all of our sources were men.

The Heyday

The Inside Track’s enormous popularity with readers gave its dynamic columnists two distinct things: the power to elevate or destroy anyone in their path, and the longest enemies list in town.

Mittman: The paper was still a very important part of everybody’s day in the late ’90s. That column was the one place in town where you could hear what was happening. They broke stories, events, inside stuff.

Raposa: My John Kerry story about that yacht was a good story. He bought a yacht, with his wife Teresa’s money, of course, for $7 million, and he parked it in Rhode Island to avoid paying tax in Massachusetts. To the tune of $500,000.

Fee: Kerry had Newport painted on the stern, and after we wrote about it they painted over it. He was tortured for a week straight, every news organization in town was chasing him. And finally he just wrote a check to the commonwealth. My other favorite Kerry story was the hydrant. They bought the place in Louisburg Square and we got a tip that Teresa was parking in front of the fire hydrant right in front of their house. So we go up there and get a picture, with her HZ 57 license plate right smack in front of the fire hydrant. About a week or two later we get a call from the same guy, you’re not going to believe this: The city is moving the fire hydrant! They moved it across the street.

Mittman: You didn’t want to get the Track Gals angry. Because if they got angry they could make it hurt. And there’s not a lot of places that have that kind of impact anymore. They could play hardball.

Rose: I think the Track Gals definitely went for the jugular, and they were ruthless if they had to be, but they had a good heart. The whole city loved them once you got over being afraid of them.

Convey: Nine point nine times out of 10, the Track Gals were right. Their error rate was very small, but people just got pissed off because they were publishing truths that people didn’t want to see publicized. That’s just the nature of gossip. They certainly made their share of enemies.

Fee: We used to put our hate mail on the wall. One time Paul Fireman wrote Pat [Purcell, owner of the Herald] and called us “those two idiots” because we wrote about how he built a “spite” house. The powers that be wouldn’t let him in The Country Club, so he built a house right on the 11th green.

Raposa: I lost count how many times we had to make up with Mark Wahlberg. He would say, Tell the girls to cut the shit.

Fee: I had to hug it out with him at some MTV party at some convention.

Raposa: God bless the Kennedys, though. No matter what we wrote about them, they took it and always said hello, wrote us little notes when we said something nice. God bless ’em. They knew how to work the media.

Fee: I went to St. John on vacation, and I was at the Skinny Legs, just chatting with the people. Where are you from? Boston. Well, your senator, Ted, was just here. He apparently chartered a boat and the motor conked out. The harbor was jam-packed with boats, so he was going to sail out. He ends up catching the mooring line and all the boats start smashing into each other. And he ran around and handed out money. So I call the PR guy. What now? I was on vacation last week in St. John. Oh no. I’ll call you right back. Then he says, I’ll confirm it all as long as you don’t write about the money.

Convey: I think that on the whole, at their height, much of the town loved the Track Gals, and the rest of the town had a grudging regard because frankly nobody else was doing what they were doing, and the column was almost always fun to read.

Patrick Lyons, owner of the Lyons Group: I paid publicists to keep my name out of the paper. In the beginning, when we were trying to build our business and scratch out an existence, it was mother’s milk to us. But then, probably in the early 2000s, I literally worked overtime to stay out. If you think about the greatest creature on Earth, the great whale, it only gets harpooned when it comes up. People know it’s under there, but the only time you stick a harpoon in a whale is when it sounds. A lot of people get a buzz out of seeing their name in the paper, but I definitely did not.

Rose: I literally would sit outside the Herald for the early edition to come out on my way home. You could not rest or go to sleep until you knew which way your client was spun by them. I can’t tell you how many nights I sat outside the Herald waiting for those first editions.

Barclay: Everybody was modest when they got in there, but they tried. We had weekly meetings: this was Trackable, that’s not Trackable, send this to the Track. At the same time, the Track Gals were scary because they would call me occasionally and ask me questions about people who had been in the Rack. I’d be afraid to tell the truth sometimes.

Soosie Lazenby, former Massachusetts Sports Commissioner; founder of SportsMatters: I worked with Nomar Garciaparra and Paul Pierce and Antoine Walker on all their foundations and fundraisers. I remember when Ben Affleck was with that Enza chick at Nomar’s event. That was one of my quintessential Inside Track moments when they blew up my phone all night.

Fee: Then Ben got sick and he was in Enza’s house for a week with the flu and all of her friends would come over to her house and then they would send emails to each other, He has a hairy back, all this stuff. Eventually all of those emails ended up in our inbox. So we wrote all about that. The next time we saw him, he lifts up his shirt and goes, I don’t have a hairy back!

Rose: The Track Gals had the ability to ruin someone’s life. And that’s when you had to beg them not to go there. I was quoted saying it was like a favor bank, and they kept score. I can still hear Gayle: So what are you going to give me if I keep this out? And I’d come up with something that would top it or at least even it out. And she’d say, But you’re going to owe me. That was your penalty. The Track Gals in their glory days, they were like Vegas, the house always wins. The Track Gals always won in the dialogue about how you were going to shape an article. They always got the last word.

Fee: I have to tell the story about how we fixed up Tom and Gisele. The Pats did this promotion every year at Gillette where they’d bring in a Victoria’s Secret angel and she would deliver frilly underwear to a random seat number. It was always some big fat guy with face paint. So they called and asked if we wanted to interview Gisele. And we were like, eh, sure. So I ask her, what do you think of Tom Brady? Well, he’s very handsome, but he has a girlfriend, so he is gay to me. Of course I put it in the paper. And they have Tom on WEEI Monday and Gerry Callahan asked if he saw the Track. Brady reads it and says, Oh, wow, that’s really harsh. A year later, our friend is in the locker room in San Diego, Pats playing the Chargers, he calls us and says you’re not going to believe who is standing outside the locker room door. Gisele! So, who fixed them up? Us, obviously!

Ernie Boch Jr., CEO of Boch Enterprises: People forget how powerful the Inside Track was, how incredibly powerful they were. It seems almost inconceivable the power the column had. It was a moment in time. It’s hard to describe. Whether the Track Gals were good for you or bad for you, they raised your profile. They got it right from the beginning, they were in the driver’s seat, and everyone else was watching them drive by. They were in control.

Bumps Along the Track

As the media business moved online, the Inside Track stood at a crossroads: How does a newspaper keep pace against the Internet, social media, and an increasingly litigious culture? The answer: invest and evolve, or die.

Convey: The Globe tried to respond in several different ways to the Inside Track through the years. The first one was some dumb beans and cod column where they tried to do gossip, but they did it like they were holding an objectionable object out in two fingers with their pinkies raised.

Jurkowitz: They didn’t have the freedom, the personality, nor the atmosphere. You couldn’t do a real gossip column like that in the Globe.

Fee: I can’t remember one story they beat us on. They thought it was beneath them. They wouldn’t put the effort in.

Raposa: Back then it was easier to engage people by phone—you knew if it was real or not. Nobody talks to each other anymore; everyone emails.

Fee: On the phone, you could put them at ease instead of emails going back and forth.

Raposa: Joe Kennedy and his annulment, that actually came from snail mail.

Fee: The Internet was hard for us. Once it was up and firing on all cylinders, you didn’t have a lot of time to work stories. It’s all Facebook and Twitter and Instagram now—you would have to break a story in, like, 10 seconds.

Raposa: Before that if someone got a pic of a celebrity they would give it to us, and we would print it and put their name on it. Now they just throw it up there.

Fee: Remember when Drew Bledsoe did that swan dive into the mosh pit at the Paradise? That was pre-Internet and people sent us all of their pics of him looking so hammered. Now that would be on Instagram in 10 seconds. And then picked up by TMZ. And they would pay. The other thing is all these Inside Track offshoots, like Barstool Sports.

Raposa: David Portnoy was working out of his parents’ basement when we knew him.

Fee: Nobody did sports gossip besides us, and then Barstool Sports came and they kind of cornered the market because they could get away with so much. They could put stuff in there without being verified or vetted. We were journalists and followed responsible journalistic rules, and none of those people did.

Barclay: Everything that’s embarrassing is plastered on social media in 30 seconds. A lot of what made the Track special isn’t special anymore. You don’t have to wait until tomorrow to look at the newspaper to find out. If someone has a gaffe or blooper, it’s there within an hour. You can’t have an opinion on it, opposition to it, it’s BOOM. Something happens and you’re dead. Fact checking, it doesn’t exist. It’s photograph, post, let the cards fall where they may.

Fee: The Herald lost a couple of libel suits. We never did.

Raposa: We’ve only been sued once. And we won.

Megan Johnson, Inside Track assistant: Tom Scholz, from the band Boston, sued the Track claiming that they said he was responsible for the suicide of the lead singer, Brad Delp.

Convey: The story happened under my watch. I read that story before it went into the paper, and I completely stood behind it then and stand behind it now. It went all the way to the Supreme Court and we won. But it probably cost the paper 5 or 6 million bucks—a paper that did not have those kinds of resources to spend. It became clear that if you got sued, it was as good as losing. Even if you won it would cost you so much that it would be a mortal wound. You could see the mentality of, why are we going to risk getting sued over a gossip column? I can understand that point of view, but I will say that as the Inside Track faded from view, the Boston journalism scene got a whole lot less interesting. And a whole lot less fun. I think in some ways you might be able to chart the rise and fall of gossip with the rise and fall of newspapers.

Johnson: The relationships between management and the Inside Track really started to fall apart. The lawsuit affected what we were allowed to write and say tremendously—constantly afraid of lawsuits, everything gone over with a fine-toothed comb in a ridiculous way. By the end, we couldn’t say “gossip column,” it had to be “entertainment journalism.”

Fee: We got a call from the doorman at the Copley Plaza, who said Taylor Swift got thrown out of the Kennedy wedding. She was dating Conor Kennedy, who was a junior in high school at the time. We finally nailed it down that she got thrown out. I called Vicki [Kennedy] and she confirmed it. The editor had the gall to say to me that he didn’t believe I really talked to Vicki, but we had a little history with her from the Michael Kennedy situation. Our editors did not put it on the front page.

Raposa: Chickenshit.

Johnson: Taylor Swift crashing the Kennedy wedding was a tremendous story for us; it went national, bigger than I had ever seen. We were absolutely killing it. But we were always in trouble. Everything was a battle. The Inside Track and sports sold the damn paper—they were so clueless about that, they chopped down the column from two pages to one. It was clear that they didn’t want us to succeed anymore. It was so dumb. They were killing really good stories, repeatedly, because they were afraid of lawsuits.

Fee: You know what was a good story, my last good story for the Track? Our buddy on the Vineyard tells me Sasha Obama is working at Nancy’s. She’s working the fried-clam window, has a little name tag that says “Natasha.” So photographer Chris Evans and I go over there. We got pics. No question that it’s her, Secret Service limo and everything. And we called the White House: Please don’t write this. Nah, we’re writing this. That story went global.

The Last Days of Gossip

Raposa left the Herald in 2013 and later opened a bakery and lunch spot in Duxbury. Fee continued the column on her own until she retired several years later. Reporter Olivia Vanni took over the revamped column until it was permanently shelved in 2020 during the pandemic. Nothing has replaced it.

Fee: Can I just say that when the Inside Track ended, a year later the Herald was bankrupt. I’m not saying that there’s any cause and effect, that’s just the facts. When Laura left in 2013, I did it all by myself until 2016. For no more money. Whoever was in charge at the time believed we were replaceable. They hired, what was her name, Olivia something or other. Who had about 27 seconds of experience.

Olivia Vanni, Inside Track columnist, 2017 to 2020: I picked it right up from Gayle. There was definitely a little bit of imposter syndrome. We wanted to switch it over from a gossip column to something that was more anchored in news and journalism. I was 26 when I started the Track; it was extremely intimidating. People kept saying, Oh, you have such big shoes to fill. It was hard, especially for a young journalist, being compared constantly to these people. It was really intimidating for me because I had to play by the rules a little bit more, not get us into lawsuits. That was a big part of it. I would have loved to do some of the stuff that they did, but the Herald was very much gun-shy. One of the first meetings that I had was with the Herald’s lawyer.

Rose: I don’t think she was as invested the way the Track Gals were. It was a lighter column, more geared to press releases. She wasn’t uncovering incredible news like they were.

Vanni: It was hard. People got used to what the Inside Track was. They were serving this juicy, delicious piece of steak and I had to turn around and suddenly say sorry, kitchen’s under new management and all I’ve got is Salisbury steak that is ethically sourced.

Convey: Boston certainly is poorer without it. But it takes resources, space, salaries, and expenses to do the kind of thing that Gayle and Laura did, and newspapers just aren’t the power that they used to be. First the Herald was limping and then it was struggling and then it was on its knees and then finally it fell flat on its face, and in a certain way the column was collateral damage. Newspapers everywhere were cutting away what was perceived as nonessential. But truthfully, gossip was one of the five major food groups. I think that you develop a deficiency, certainly as a tabloid newspaper, if you don’t provide that to your readers. It was a symptom of an underlying disease when they whacked the Inside Track.

Boch Jr.: The Internet is the Inside Track every day, naming names and people making shit up and everything. It’s there. But they had this crazy power, matched with legitimacy, matched with a daily dose. It was nuts. The Inside Track had its moment and had its day.

Lyons: People want to know about celebrities, and not just celebrities: It’s really the intersection of society, entertainment, business, and politics. And nobody really reports on it now. And if you don’t believe that this type of information is relevant or vital—Kourtney Kardashian, 150 million Instagram followers? Wake up and smell the java. It speaks to the voracious appetite that the public has, and when you don’t pay attention, you just contribute to your own irrelevance. If you’re a responsible interpreter of the times, and a publisher, you’re doing your readers a disservice by not doing this. There are new, young, smart people that are jockeying for a position right now, and they deserve notice. The Storybook Ball will be back and somebody will secure a walk-on to a Mark Wahlberg movie for his wife, and guess what, people want to know about that.

Fee: I live on the Cape and then I go to Florida in the winter. So basically I do nothing but go to the beach and play golf and play with my grandson. I was sitting on the beach in Florida when Bob Kraft got arrested and my phone was ringing off the hook with people saying, You have to come back!

Raposa: That was one of maybe three times I thought to myself, Ahh, this is so good I wish I could go back! Gayle and I were going back and forth, texting, texting, texting. Some guy came in the restaurant and was like, What’s the story?

Fee: People still think we are their personal gossip column. Sitting here laughing about it now, yeah, I miss it. But it would not be the same now as it was then. Who would we write for?

Rose: I think Boston now is the Wild West—anybody can do anything and get away with it without any repercussions. The Track Gals held the city accountable for our actions. There’s social media and Barstool, but the Track Gals were relentless, they were like pit bulls and they always got their story. The Track Gals were just magnificent at what they did. The city isn’t the same without them.