Mobsters are no saints, and as one of the most influential Cosa Nostra members in New Jersey, Tony Soprano was a man of many sins. Among the things The Sopranos‘ central character enjoyed the most was breaking the sixth and seventh biblical commandments. Whenever he wasn’t killing someone, he was bedding a random woman or a long-term mistress. While all this was happening, Carmela was sitting at home, enjoying the splendor that came with being a mob wife.
The show constantly emphasized that having a goomah (mistress) is a common practice in the mob. But even though Carmela knew what was going on, she was still hurt by it. She tried to revenge-cheat by kissing the home decorator, Vic Musto, flirting with Tony’s lackey, Furio, and sleeping with A.J.’s guidance counselor, Robert Wegler, but she couldn’t keep up with Tony.
Regarding promiscuity matters, Tony was prolific enough to make Wilt Chamberlain jealous. After all, he had the money, the influence, and the natural spirit of a lothario. So, what do Tony’s infidelity statistics look like? Here is everyone the mobster cheated with, in order, as far as we know.
16 Charmaine Bucco
Pre-series
At the start of The Sopranos, Charmaine is revealed to have been married to Tony’s long-term friend, Artie, for years. Fans soon learn that she and the gangster have a history. Tired of Carmela treating her like the help, Charmaine deliberately spites her by revealing that she slept with Tony back in their high school days. According to her, the incident happened when Carmela was on a trip with her parents.
Tony Started Young
Charmaine’s confession confirms that Tony’s infidelity isn’t a new thing. His wandering eye didn’t emerge because he acquired influence and a fortune. He was always looking for a new partner to play with. Throughout the series, it feels like Tony has never really gotten over Charmaine. He calls her while he is at the Plaza Hotel and dreams about her. She, too, would never have brought it up if she wasn’t a little jealous of Carmela, though the pair never crosses that line as adults.
15 Lorraine “Lady Shylock” Calluzo
Pre-series
In the Season 5 episode, “Rat Pack,” it is revealed that Tony used to sleep with Lorraine “Lady Shylock” Calluzo before the start of the series. She is a loan shark and Lupertazzi crime family associate who has a reputation for collecting. She gets into trouble when she refuses to kick up her payments to Johnny Sack. Consequently, Phil Leotardo sends men to kill her.
Breaking Protocol?
For a long time, it is implied that Tony isn’t interested in women who are gangsters like him. After all, he rejects the Camorra mob boss, Annalisa Zucca when she throws herself at him in Season 2. He argues it would be bad for business. It’s thus interesting to find out that he never had the same reservations regarding Lorraine. When she and Tony reunite, he doesn’t seem to hold any feelings for her, proving she was only a one-time fling.
14 Irina Petsin
“Pilot” (Season 1, Episode 1)
For four seasons, the story of Tony and Irina unfolds leisurely under the attentive eyes of the viewers. The two alternate between being a marvel together, and being toxic. For a long time, Irina’s fascination with the mobster seeps through as she searches for direction, meaning, and a sense of self. Tony ultimately gets tired of her and when she learns he has been sleeping with his cousin and she shares those details with Carmela.
Tony’s Most Impactful Mistress
Irina appears on the show irregularly, but survives longer than any other mistress. Tony keeps her around for so long because he also cares about her, and Irina’s time with Assemblyman Zellman proves she always deserved better. He pays for her English classes and helps her adjust to American life better. Sadly, Tony refuses to let the two date in peace. He embarrasses Zellman by beating him with a belt. As expected, a breakup follows.
13 Connie DeSapio
“House Arrest” (Season 2, Episode 11)
Connie DeSapio is introduced as an office assistant at Barone Sanitation, a garbage company that serves as a front for illegal businesses conducted by Tony’s crew. When Tony heads there to meet the owner, he is introduced to Connie, who he immediately takes a liking to. When the doctor recommends that Tony work on ways to relieve his stress, the camera cuts to Tony and Connie having sex in the office.
No Seduction Hurdle Is Too Big for Tony
What’s funny about Connie is she’s supposed to be an impossible target. When Tony remarks about her perfect figure, he is informed that she is born again, hence a mobster like him should stand no chance. Moments later, we learn that she is actually “p*rn again.” No surprises there, considering that she works in a mob-tied company. Regrettably, she serves no narrative purpose beyond proving that Tony is a brilliant seducer.
12 Mandee
“University” (Season 3, Episode 6)
“University” is one of the show’s most violent episodes, with most of the chaos stemming from Ralph. He beats his girlfriend, Tracee, to death when she questions his manliness and almost takes out Georgie’s eye while attempting to reenact a scene from Gladiator. Well, it is stated that Tony would have prevented the latter, had he not been busy receiving oral from Mandee in the VIP room.
Not One of Tony’s Proudest Moments
Tony’s newest pleasure provider never utters a word, making it hard to see where she stands or what she represents. All that can be said is that Tony really needs to be more mindful about the affairs of workers associated with any of the DiMeo crime family’s business. Earlier, Georgie lets out a disgusting detail, telling a new dancer that in order for anyone to work in the VIP room, they have to give him $50 plus oral later on.
11 Gloria Trillo
“He Is Risen” (Season 3, Episode 8)
David Chase might not mention it, but perhaps Gloria Trillo was inspired by Miss Forrest from Fatal Attraction. Tony first meets the lovelorn car saleswoman in Dr. Melfi’s waiting room. He then shoots his shot and an affair begins. Unfortunately for him, she is a cheating man’s worst nightmare. Chaos soon bubbles up around the lovebirds when Gloria becomes increasingly clingy, forcing Tony to resort to aggressive tactics to scare her off.
The One Tony Regrets the Most
The entire Gloria Trillo plot is a scathing satire on infidelity and greed. The character herself is a perfect reminder that love can mollify only when it is radiated by both parties. The Trillo affair also symbolizes a trap for Carmela and a comeuppance for Tony. Just an episode earlier, Carmela had been advised by Dr. Krakower to leave him. Now there is another mistress.
For Tony, Trillo’s antics serve as mild payback for all the cheating he has done. But it doesn’t stick, as shortly after the Gloria Trillo scare, Tony continues with his skirt-chasing ways.
10 Miss Reykjavik
“Everybody Hurt” (Season 4, Episode 6)
Early in Season 4, the New Jersey mobsters are spotted enjoying a Caligula-like party with a few Icelandic flight attendants. One of them, Miss Reykjavik, becomes Tony’s temporary goomah. When Artie gets whopped while trying to collect a debt from Jean-Philippe, he calls Tony. When Tony picks up the call, Miss Reykjavik is seen next to him, confirming that their affair is cruising without any turbulence.
Vanished Too Soon
Miss Reykjavik is a fun YOLO character. It’s a shame she never stuck around for long. Blame Artie for interrupting the beautiful moment between a woman who serves bodies in the skies and a man who puts bodies on the ground. It’s also interesting how Miss Reykjavik gets introduced shortly after Hugh tells his story of how he contracted diverticulitis while stationed in Iceland. That’s but a testament to the awesomeness of The Sopranos.
9 Valentina La Paz
“Mergers and Acquisitions” (Season 4, Episode 8)
Tony might not have had the makings of a varsity athlete, but he always had the makings of a goomah-stealer. Valentina is introduced as the girlfriend of Capo Ralph Cifaretto, and when Tony sees her at the stables, he decides to take her for himself. The decision turns out to be one Tony later regrets. At one point, her nail falls into Tony’s pocket and Carmela finds it. Angered, she heads to a spot where Tony hides cash and plucks some dollars for herself. She later initiates divorce proceedings.
Could Have Evolved Into Something Bigger
Valentina appears emotionally stable, compared to many of Tony’s other mistresses. More so, there emerges a major window for her to graduate to wife. When Carmela leaves Tony, he continues seeing Valentina, and she appears to have genuine love for him. She even suggests that they travel to Antigua for a romantic retreat. Clearly, she sees a future, but Tony isn’t so sure. When her hair gets burned during a fire accident, the DiMeo crime family’s Don takes this as an opportunity to leave her for good.
8 Svetlana Kirilenko
(Season 4, Episode 10)
Svetlana, the cousin of his ex-Comare, gets a job as Livia’s live-in nurse and, later, as Junior’s caregiver. Having developed osteosarcoma when she was a child, she had her leg amputated. Though she first appears in Season 2, Tony takes some time before sleeping with her. It’s the discovery of this particular affair that angers Irina, prompting her to call Carmela and share all the tea regarding Tony’s bed-hopping spree.
Arguably the Toughest of Tony’s Mistresses
It’s impossible not to like Svetlana. She loves her vodka, works hard, and never lets anyone take her for granted. When Tony’s sister, Janice, takes her prosthetic leg during her feud, she sends the Russian mob after her. On top of that, Svetlana has a realistic outlook on sex and love. She is quick to nip the affair in the bud instead of letting Tony use her for long and calls him out on several issues.
“That’s the trouble with you Americans. You expect nothing bad ever to happen when the rest of the world expects
only
bad to happen—and they are not disappointed.”
Unlike other mistresses, she and Tony engage intellectually on several topics, and she comes out on top.
7 A Weightlifter and a Preschool Assistant
“Whitecaps” (Season 4, Episode 13)
“Whitecaps” cemented Carmela and Tony as one of the most troubled TV couples ever. Earlier, Tony shows Carmela a beach house and promises to buy it for her. They kiss, and they reminisce.
“When we were piss-poor, this was the biggest caviar wish we could come up with. Kind of reminds you of the Kennedy compound, don’t it?”
Later, Tony’s mistress, Irina, calls the home phone and confesses to Carmela. Hell breaks loose, and at this point, she brings up other people Tony has been seeing: a weightlifter and a preschool assistant.”
The Straw that Broke Carmela’s Back
A preschool assistant is right up within Tony’s taxonomy of preferred goomahs. A weightlifter might seem odd, but it makes sense considering that a photo of heavyweight champ Rocky Marciano can be spotted behind him at one point.
Circling back to Carmela, her mob wife mentality shines brightly here. Like other women who are married to Cosa Nostra figures, she has largely come to accept her husband’s philandering, but to have such heavy information dumped into her ears is more than she can take. She never wanted her husband’s extracurricular activities to trickle into their home. Understandably, she becomes angry and confused.
6 Unnamed Dermatologist
“Cold Cuts” (Season 5, Episode 10)
The dermatologist first appears in the Season 5 episode “Irregular Around the Margins.” She fits the profile of Tony’s conquests and as he is getting treated, he tries to hit on her. Interestingly, she rebuffs his advances. Fast forward to “Cold Cuts’ and there she is, coming down his stairs. The dermatologist does a little walk of shame when Paulie comes to see Tony at Livia’s house.
The Don Knows How to Turn Things Around
The pickup attempt initially appeared to have hit a cul-de-sac, so it would have been nice to see how Tony turned the tide in his favor. But as Lefty from Donnie Brasco would tell you, there is nothing more to say here. Want more details about the seduction process? Fuhgeddaboudit. The Don gets what the Don wants. Just know that whenever the Don shoots, he doesn’t miss.
5 Unnamed Escort at the Plaza Hotel
“The Test Dream” (Season 5, Episode 11)
As Tony is staying in a luxury suite at the Plaza Hotel, he tries to call Charmaine Bucco, only for her to shut him down. He then sees a TV commercial for the Ladies of Jade escort service. This awakens his libido, causing him to make an order. When she arrives, the two have sex. Unfortunately, Tony doesn’t get to wallow in post-coital bliss for too long, since news of Tony Blundetto’s blunders arrives shortly after.
A Quick Tryst Born Out of Boredom and Frustration
“The Test Dream,” is undoubtedly one of the finest episodes of The Sopranos. It adequately digs into Tony’s psychological framework. Apart from packing in a few weird dreams, the episode paints Tony as a failing conquistador. Because he has always gotten what he wants, he becomes frustrated when Charmaine refuses to spare any time for him. While checking into the hotel, he also bumps into his psychiatrist, Dr. Melfi, another person who rejected him. Sleeping with an escort is, therefore, more of a consolation.
4 Julianna Skiff
“Johnny Cakes” (Season 6, Episode 8)
Tony is initially hesitant when the realtor Julianna Skiff approaches him with an offer to purchase the building that houses Caputo’s Live Poultry. He believes that mom-and-pop stores give the neighborhood its identity, but he softens up when Skiff makes him an ‘offer he can’t refuse.’ It gets even better when she implies she might throw her nether regions into the deal. The two later go to her home to sign papers and once they are done, they start kissing.
A Rare Moment of Regret
For once, Tonny demonstrates uncharacteristic restraint. After kissing, Julianna unbuttons Tony’s shirt, only for the mobster to change his mind and leave. The decision is influenced by Carmela’s recent actions. He not only remembers how she took good care of him after he had been shot but also how he buttoned his shirt.
But who was Tony fooling? Days later, he puts a reverse gear on his ‘regretful moment’ and tries to seduce Julianna again. This time, she rejects him. And in a move that hurts him even more, she settles for Christopher.
3 Unnamed Bada Bing Dancer
“Cold Stones” (Season 6, Episode 11)
When the cat is away, the mice will play. But Tony has never really waited for Carmela to be absent to cheat. Still, he is seen enjoying her absence this time. As Carmela has the time of her life in Paris, Tony gets busy with a Bada Bing dancer. A shot of her staring at Duccio di Buoninsegna’s iconic painting, Madonna and Child, cuts to Tony getting oral sex from the dancer as he is driving.
Disproportionate Love
Like the unnamed escort in “Remember When,” the Bada Bing dancer only exists as a marker to highlight Tony’s flaws. Just before she left for Paris, Carmella had reminded him that she loved him. She even asked him if he remembered her saying those exact words while he was admitted to hospital, and he bluntly responded with a “No!” There is clearly an imbalance in affection, but that’s part of what makes the dynamic between these two characters so great.
2 Unnamed Escort
“Remember When” (Season 6, Episode 15)
“Remember When” is quite a tense episode. Tony and Paulie head to Miami to lie low when the FBI recovers the body of bookie Willie Overall (the person Tony made his bones with) after the capo Larry Boy Barese turns into a ‘rat’ and sings. Tony also contemplates killing Paulie on a boat for telling Johnny Sack about Ralph’s insensitive joke about Ginny Sack.
The best moment comes when Tony and Paulie are having dinner. They are both shown to have acquired fresh dates and when Paulie begins reminiscing, Tony shuts him down with the iconic quote,
“Remember when’ is the lowest form of conversation.”
Fun Is a Priority for Tony
The unnamed escort doesn’t affect the plot in any major way. Her presence only serves as a reminder that Tony is the ultimate hedonist. Even when the future doesn’t look too good for him, he still finds time to tend to his carnal desires. In addition to that, the escort’s presence emphasizes a major rule about “this thing of ours.”
Mobsters are not supposed to talk freely, especially when around non-mobsters, so Tony is understandably annoyed when Paulie starts reminiscing in front of their dates.
1 Sonya Aragon
“Kennedy and Heidi” (Season 6, Episode, 18)
Very ‘noble’ of Tony to canoodle with the ex-flame of a mobster that he killed. Shortly after murdering Christopher, Tony heads to Las Vegas, where he meets the capo’s former girlfriend, Sonya. He informs her of Christopher’s death (omitting the part where he pinched Christopher’s nose after a car accident and caused him to die of asphyxiation), before offering himself as a shoulder to cry on.
Sonya Represents Tony’s Lack of Remorse and Loyalty
Christopher was one of Tony’s favorite lieutenants and, at one point, he even saw him as the future boss of the family. Sadly, drug problems prevented the capo from reaching his true potential. Because he was more of a father figure to the man, Tony would have been expected to feel a little remorseful, but he wasn’t. To him, Chris was gone and life had to move on. In the episode, he links up with Sonya, sleeps with her, and unapologetically flaunts her during his gambling escapades inside Vegas casinos.
