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This Past Weekend w/ Theo Von

#616 - Retired Boston Detective

with Kara Connolly

Published October 9, 2025
Visit Podcast Website

About This Episode

Retired Boston police detective Kara Connolly discusses her 31-year career, from working busy 1990s patrol beats in Dorchester and South Boston to becoming a detective and later joining the human trafficking unit. She shares detailed stories about major cases, including armed robberies, a man who cut off his own penis, a baby abandoned in a trash can, long-term human trafficking investigations, and undercover stings targeting sex buyers. The conversation also explores how TV crime shows affect juries, the impact of politics and prosecutors on street-level policing, the emotional toll of the job, and how she is transitioning into retirement in South Carolina.

Topics Covered

First responders Criminal psychology Human trafficking Prostitution and sex work Homelessness and drug addiction Immigration policy and border security Mental health Violence and self-defense Online pornography and OnlyFans Police work and detective work

Disclaimer: We provide independent summaries of podcasts and are not affiliated with or endorsed in any way by any podcast or creator. All podcast names and content are the property of their respective owners. The views and opinions expressed within the podcasts belong solely to the original hosts and guests and do not reflect the views or positions of Summapod.

Quick Takeaways

  • Kara Connolly spent 31 years with the Boston Police Department, transitioning from high-crime 1990s patrol work to detective work and eventually the human trafficking unit.
  • Television crime dramas have created unrealistic expectations among juries, making prosecutions harder when cases lack fingerprints, DNA, or dramatic forensic evidence.
  • Most sex trafficking cases she saw involved local, vulnerable girls groomed by manipulative pimps rather than sensational kidnappings or strangers in shipping containers.
  • Kara describes extremely graphic and disturbing cases, such as a mentally ill man cutting off his own penis and a woman secretly giving birth and leaving her baby in a trash can, highlighting the psychological toll of police work.
  • Changes in prosecutorial priorities and local politics, including decisions not to prosecute certain property crimes, have contributed to rampant shoplifting and open-air drug scenes in cities.
  • Undercover 'John stings' showed that buyers came from all walks of life-doctors, professors, tradesmen-and many sought unprotected sex, often while married.
  • A three-year human trafficking investigation with federal agents led to a violent pimp receiving a roughly 33-year federal sentence for exploiting dozens of women across multiple states.
  • Kara emphasizes the importance of dark humor and strong camaraderie among officers as coping mechanisms for the trauma and chaos they regularly face.
  • She believes fewer people want to become police officers now due to political hostility and lack of institutional support, which affects staffing and morale.
  • In retirement, she has relocated near Charleston, South Carolina, focusing on painting, the beach, and family life after decades of high-stress service.

Podcast Notes

Introduction and guest background

Content warning and guest intro

Host gives a graphic content warning about intense police and detective work stories[0:35]
• He notes some conversation will be graphic and encourages listeners who are sensitive to make their own choice about listening
Kara's career overview[1:06]
• She is introduced as a retired Boston police officer and detective with over 20 years on the force before joining the human trafficking unit
• Later she clarifies she served 31 years total on the Boston Police Department

Light opening chat about stress and hair loss

Conversation about stress-related hair loss and coping[1:09]
• They compare experiences of losing hair from stress and finding hair on pillows and in sinks
• Kara mentions using Minoxidil via an online service when she could not get a timely doctor's appointment, saying it led to regrowth in about three months
• They talk briefly about trying to reduce stress and focusing on doing enjoyable activities
Formal on-air introduction[2:22]
• Host thanks 'Kara Connolly' for joining and reiterates she is a retired Boston police officer and detective
• Kara confirms she was on the force for 31 years

Early years in patrol and community context

Probationary period and first assignments

Explanation of police probation after academy[2:54]
• After graduating the police academy, new officers go through a probationary period (six months when she started; now one year)
• During probation, they are rotated through different districts, including a busy and a quiet one, to evaluate performance and behavior
Dorchester and South Boston experience[3:41]
• Kara was born in South Boston but initially worked in Dorchester and South Boston after the academy
• Dorchester was very busy in the 1990s with many shootings and gang-related incidents, while South Boston was relatively quiet

Demographics and local culture ('Southie')

Demographics of Dorchester vs. South Boston[4:02]
• Kara describes Dorchester at the time as having a lot of Black residents, some white and some Asian
• South Boston was mostly white with some Black and Latino residents
Meaning of 'Southie' and local attitudes[4:35]
• She explains 'Southie' is a nickname for South Boston and is not properly pluralized as 'Southies'
• She says she grew up saying 'South Boston' rather than 'Southie', though many people use the nickname
• Kara notes that 'Southie' became widely known through movies like 'Good Will Hunting', leading outsiders to adopt the term incorrectly
Community relationship with police in South Boston[5:02]
• Kara states that people in South Boston generally liked the cops compared to some other parts of the city
• She adds that most of her 'crazy' or intense calls came later as a detective; patrol work in South Boston had been relatively quiet for her

Early high-adrenaline calls as a patrol officer

First 'person with a gun' call[5:53]
• Kara recalls her first 'person with a gun' call and feeling terrified and flooded with adrenaline while driving to the scene
• The call turned out to be unfounded, which she says is common; many alarming calls prove to be 'nothing burgers' once officers arrive

Policing in the 1990s vs. now and community policing

Violent crime rates in Boston over time

Homicide and gang violence in early 1990s[6:40]
• Kara recalls that in the early 1990s Boston's annual homicides peaked around 150-160, with many shootings and gang activity
• They reference a figure from 1990 showing 152 homicides, much of it youth gun violence driven by gangs, crack cocaine, and easy access to handguns
• She notes that now Boston has about 35 homicides per year, reflecting a major decline and safer conditions

Community policing and walking beats

Concept of community policing[7:39]
• Kara says 'community policing' began when she was new on the job and involved walking beats instead of working solely from cruisers
• Officers were assigned to walk specific stretches of main streets to get to know residents and encourage them to feel comfortable talking to police
• She notes that when she started in Dorchester there were about seven or eight walking beats; now there are only a few and they have been reintroduced after being reduced
Limitations of walking beats in high-crime neighborhoods[8:20]
• Kara points out that walking beats were placed in the worst neighborhoods where residents often did not want to talk to police, limiting the effectiveness of the model

Modern image management and 'dancing cops'

Use of social media to soften police image[8:33]
• Kara criticizes departments' social media campaigns featuring 'dancing cops' or officers playing basketball with kids, calling them 'cringy'
• She says departments are trying to look friendly and non-paramilitary, especially during periods like COVID or on events such as 'women in law enforcement day', but she and her colleagues found the videos embarrassing

Becoming a detective and notable early detective work

Promotion process and role differences

Exam and interview process for detective[9:38]
• Back then, becoming a detective required a written exam based on multiple textbooks, followed by an oral interview
• Scores from the test, interview, and years of experience were combined to decide who would be promoted
Differences between patrol officer and detective work[10:15]
• Detectives do not wear uniforms, which Kara says was her favorite part of the new role
• Patrol officers respond to calls, write reports, and are done unless they later go to court; detectives are assigned those reports and 'own' the case from follow-up to court

Desire for promotion and career timing

Long wait between detective exams[11:19]
• Kara was a patrol officer for 13 years, in part because there was a seven-year gap between detective exams when she had planned to sit for the 'next one' after having a child
• She notes that most patrol officers eventually want promotion to detective or supervisory ranks, though some are content to remain patrol officers their entire careers

Memorable early armed robbery case

Halloween T-Mobile robbery[11:42]
• On a Halloween morning, two armed men robbed a cell phone store in a rough part of town, tying up a young woman employee with telephone cord and stealing about $785
• The robbery was fully captured on video, including a gun held to the victim's head and her later hopping while bound to call for help by knocking the phone off the hook with her head
Quick police response and evidence trail[12:57]
• Officers from Dorchester flooded the area; one of Kara's academy classmates noticed two men walking in a nicer pocket of a bad neighborhood who matched the clothing description and seemed out of place
• A trail of discarded jackets and hats led back toward the crime scene; one suspect wore gloves and the other had bandaids and tape around his fingers to avoid leaving fingerprints
• Another officer found the guns in a trash can and someone found the cash box; the case came together quickly through coordinated work
Federal prosecution and sentencing[12:33]
• Because the victim business was T-Mobile, federal authorities took the case under a commerce rationale that the robbery affected interstate commerce
• The suspects had serious criminal records, including multiple other armed robberies, and received sentences of over 20 years each in federal court
• Their truck-driver brother had bought guns in Arizona and brought them back to Massachusetts; he ultimately testified against them and was not prosecuted

Forensics, TV influence, and case workload

Fingerprinting in real investigations

Importance and limitations of fingerprints[13:44]
• Fingerprints are important because each person's are unique and, if found at a crime scene, leave little innocent explanation for being present
• However, prints are not always obtainable or useful, such as on dirty or heavily trafficked surfaces like bank counters with thousands of overlapping prints
How fingerprints are lifted[15:42]
• Detectives, rather than separate technicians, often dust for prints in Boston except in major incidents like homicides where forensic units are called
• She explains that powder is applied to smooth, clean surfaces (like granite countertops) to reveal latent prints, which are then lifted with clear adhesive tape

Impact of TV crime shows on juries

Unrealistic expectations from 'CSI' style shows[16:21]
• Kara says TV shows like 'CSI' have 'ruined' prosecutions because juries now expect bags of physical evidence, DNA, fingerprints, and forensics in every case
• She notes jurors sometimes send notes asking why there are no fingerprints or DNA, not understanding that many real-world cases generate little or no recoverable forensic evidence
Clarifying the 'First 48' misconception[17:17]
• Kara confirms detectives are not literally limited to 48 hours to solve a case, but early hours are critical before new serious cases divert attention
• She notes that a single day can bring multiple major incidents (shootings, stabbings, armed robberies, missing persons), stretching detectives thin

Prioritizing cases and impact on personal life

How detectives triage cases[18:14]
• Violent crimes like shootings, stabbings, and armed robberies take priority because of the dangerous offenders involved, whereas fraud or identity theft, though serious to victims, can wait
Long hours and missed family events[17:47]
• Kara describes frequently staying late when major incidents came in near shift end, sometimes working until midnight instead of going home
• She recalls having to call home to say she could not make dinner or help with her children's projects because 'someone got stabbed' and emphasizes the strain on family life

Holidays, schedules, and moving into human trafficking work

Holiday scheduling in Boston PD

Holiday rotation system[19:25]
• Officers worked holidays on a rotation where each officer got all major holidays off only once every six years
• On the 'good' holiday year, an officer would have Easter, Thanksgiving, Christmas, New Year's, etc., off; then it would be another six years before that happened again

Reason for transferring to human trafficking unit

Seeking a more stable schedule[20:00]
• Kara transferred from a busy district detective assignment to the human trafficking unit partly because it offered a more regular Monday-Friday schedule, making family life easier

Graphic and extreme cases as a detective

Self-amputation case: 'dick on the sidewalk'

Initial bizarre call and discovery[21:15]
• Near the end of her career, Kara handled a series of shocking cases; one started with a radio call about 'a piece of male anatomy on the sidewalk'
• Dispatchers and officers initially thought the call was a joke until they saw the text indicating it came from a nearby health center reporting a penis on the ground with blood everywhere
Following the blood trail and finding the victim[21:59]
• Patrol officers located the severed penis and followed a trail of blood several hundred yards to a three-family house where the blood intensified up the stairs
• Inside, they found a young man sitting in a chair, covering his crotch and silently staring; the apartment was a 'blood bath' with blood on the bedroom floor and a sink full of blood
• It turned out to be a group home for mentally ill people, but no staff were present; two newer officers had to handle the gruesome scene
Frozen tissue and forensic logistics[22:55]
• Initially, responders assumed someone had bled out and died; upon learning the man was alive and claiming 'I did it', EMTs decided to collect the severed organ to attempt reattachment
• The penis had frozen to the sidewalk due to the cold; when an EMT tugged it loose, a streamer-like internal tissue protruded, which Kara likened to sausage casing or a 'balloon streamer' and almost vomited from seeing
Video review reveals disturbing sequence[23:43]
• Later video footage showed the man walking completely naked down a busy street in the early morning without anyone calling police
• He had partially severed the penis earlier in the house; on camera he bent over, tugged it off entirely, and threw it onto the sidewalk
• He then walked about a mile, returned, knelt down, kissed the severed organ, and walked back home, behavior Kara found 'fucking crazy'
Mental illness and aftermath[24:53]
• The man was in his early 20s and severely mentally ill; he had previously cut off his own nipples 'to let the devil out' and carved something into his forehead
• Doctors attempted to reattach the penis but it failed and had to be removed after about a month; she imagines that cold temperatures and coagulation likely prevented him from bleeding to death
• Kara recalls calling the group home supervisor, who admitted they had been trying to place him in a psychiatric facility because he was 'exposing his penis in group classes'; she informed him bluntly that he had now cut it off and thrown it on the sidewalk

Baby abandoned in trash can

Initial call from elderly resident[26:37]
• An elderly man in senior housing called 911 saying someone (his cleaning woman) had given birth in his apartment and left with the crying baby in a bag
• Responding officers found his apartment pristine with no signs of childbirth; thinking he might be delusional, they called an ambulance for a psychiatric evaluation
Discovery of the baby in a street trash can[29:00]
• Simultaneously, a woman walking on Dorchester Ave heard crying from a wrought-iron trash can and flagged down arriving EMTs, saying she thought there was a baby or animals inside
• Initially skeptical, the EMT casually checked the can, then reacted dramatically when he pulled out a baby, triggering a flurry of activity and radio traffic
• The woman who found the baby likely saved its life, as it was cold out and city trash collection could have removed the infant unnoticed
Identifying the mother through legwork and phone pings[29:05]
• The elderly man said 'the cleaning woman' had been in the bathroom for hours, borrowed scissors and a bag, then left with what sounded like a crying baby in a tote
• She had only signed a first name and a phone number on the building log; officers blocking traffic used that number to search reports and link it to a different full name and car registration
• With the true identity, they pinged her phone as it moved from the scene onto public transit and then to her home in Milton, while detectives and an ambulance went to intercept her there
Mother's condition, motives, and legal outcome[30:14]
• At her residence, officers found no baby-related items despite the child being full-term, indicating she had no intention of keeping the baby
• She was medically fine and stayed in the hospital for a few days; Kara says the woman had deliberately tied the bag in a knot in an apparent attempt to kill the baby
• The homicide unit took the case; it took about four years to go through court and resulted in probation with no jail time, which Kara and colleagues strongly disagreed with, calling it attempted murder
• She reports that the defense claimed a 'cultural' explanation (the woman was Haitian), which Kara rejects, saying there is no culture where throwing babies in trash cans is normal

Psychological toll, coping, and examples of traumatic scenes

Coping with horror and gallows humor

Why officers laugh at crime scenes[32:05]
• Kara explains that laughing at murder or gruesome scenes is a tension-release mechanism and a way to protect one's mind from trauma, not a sign of disrespect to victims
• She says over time she handled such events better than when she was new, viewing this adaptation as a mental safety mechanism

Example from another officer: suicide in front of mother

Host recounts LA officer's story[33:09]
• The host shares a prior guest's story of responding to a suicidal subject, only to witness the man shoot himself with a shotgun in front of his mother while they were talking outside
• That officer had to console the mother and secure the scene, later describing pushing the heavy body aside to enter and having brain matter fall down his back from the ceiling
• Kara notes that few professions besides police, EMTs, and firefighters encounter such horror in the course of regular work

Politics, prosecutors, and urban disorder

Effect of DAs and mayors on policing

Varying levels of support from leadership[34:32]
• Kara says policing is now highly politicized and the degree of support from mayors and district attorneys (DAs) significantly affects street-level work
• She describes some elected DAs who announced they would no longer prosecute offenses like vandalism, larceny, and shoplifting, despite those still being crimes under state law
Consequences of non-prosecution policies[35:06]
• Businesses still call police when people steal large amounts of goods, but if DAs decline to prosecute, it leads to widespread theft and stores locking up products
• She cites a case where one man and his brother stole about $30,000 of merchandise in a month through repeated thefts at CVS, Walmart, and Walgreens
• Kara argues that when DAs refuse to prosecute property crimes, victims-from big stores to individual homeowners-are effectively ignored
Current DA vs previous controversial DA[36:16]
• She praises current Suffolk County DA Kevin Hayden as more supportive and collaborative with police
• She criticizes former DA Rachael Rollins for policies decriminalizing certain offenses and mentions Rollins later resigned as a U.S. Attorney amid ethics investigations

Homelessness, open-air drug scenes, and city decline

Mass and Cass in Boston[37:10]
• Kara describes 'Mass and Cass' (Massachusetts Ave and Melnea Cass Blvd) as an area overtaken by drug users, tents, and disorder, with safe injection sites and public defecation
• She notes that needles and human waste now appear across the South End, affecting residents who pay high prices for housing and find people breaking into properties simply to sleep and defecate
Comparison with other cities[37:56]
• Kara says similar patterns of decline and encampments are evident in cities like Austin, Seattle, and Portland, which she recalls previously enjoying
• She recounts returning to Austin and seeing homeless people sleeping in hammocks attached to street signs along 6th Street, scaring her daughter

Border policy analogy and quality-of-life concerns

Concern for residents in border towns and neighborhoods[38:35]
• The host emphasizes caring about the perspective of residents near the U.S. border who fear people running through their neighborhoods at night, regardless of migrants' intentions
• Kara frames these issues-both border and local crime-as 'quality of life' problems that leaders insulated in affluent areas do not experience directly

Human trafficking unit and realities of sex trafficking

Understanding human trafficking beyond media myths

Definition in her work and mismatch with public imagery[41:44]
• Kara says she initially thought human trafficking meant movie-style kidnappings and forced prostitution by strangers, but her real cases rarely looked like that
• In her experience, trafficking typically involved people exploited for sex through coercion, threats, or manipulation, rather than dramatic abductions

Grooming tactics and 'boyfriend' pimps

Common backgrounds of victims[41:55]
• Most victims she saw were local girls from the city or nearby suburbs who had adverse backgrounds: sexual abuse, single-parent homes, foster care, or emotionally absent parents
• She notes pimps exploited emotional needs, such as a lack of attention or love at home, to draw girls in
Example: music video promise and rapid exploitation[42:25]
• In one case, a teenage girl was approached while walking down the street by a man offering to put her in a music video; after shooting some footage, he lured her to another state and began selling her for sex online
• She was told she would be photographed and then had to have sex with multiple men for money she never controlled
Example: long grooming via texts[42:18]
• Kara recounts a text thread where a pimp slowly groomed a girl who worked in a store, bringing her food and money and referring to her sweetly over about a month
• The girl then called him her boyfriend, and soon after he demanded she service seven men at a party, keeping all the proceeds and denying her even a small portion for herself

Asian massage parlors and transnational elements

Challenges investigating spa-based trafficking[43:43]
• She says Asian-run spas were different: women were moved frequently between states like New York and New Jersey, making it difficult to build cases
• Language barriers were severe, as many women spoke dialects that even Chinese-speaking officers could not understand, and they often did not know or share their real names
• Kara mentions finding baby turtles in a sink at one spa and notes that women sometimes slept on the massage beds at night, underscoring the exploitative conditions

Targeting sex buyers through 'John stings'

Shift from arresting prostituted women to buyers

European model of focusing on demand[45:01]
• Kara explains their unit adopted a European-inspired strategy to target sex buyers ('Johns'), reasoning that without demand there would be less exploitation
• Previously, enforcement focused more on arresting prostituted women, but the unit shifted emphasis to those paying for sex

Setting up online ads and code language

Using Craigslist and Backpage[45:27]
• They placed undercover ads on Craigslist and later Backpage, which allowed paid 'bumps' to keep listings at the top; she believes newer platforms like Instagram or TikTok may now fill that role
Understanding and using acronyms[45:51]
• Kara learned the code acronyms used in ads: 'GFE' (girlfriend experience, including kissing), 'full service' (sex and oral), 'Russian' (breast-focused sexual activity), 'Greek' (anal), and 'BBBJ' or 'bareback' (sex without a condom)
• Buyers would use these terms, thinking they were avoiding explicit language and thus legal trouble, but detectives testified based on training that the acronyms referred to sexual acts

Kara's role as undercover 'prostitute'

Establishing probable cause on the phone[46:33]
• Kara herself posed as the woman in the ads, talking to callers on the phone and agreeing to sexual services for specified prices to establish probable cause before they arrived
• She notes that some callers were nervous and chatty while seasoned buyers went 'right to business', and she grew more comfortable over time making explicit arrangements while fellow officers listened and laughed
Hotel operations and arrest process[47:10]
• They used hotel rooms (sometimes donated by high-end hotels) where Kara opened the door and officers hid nearby; by the time a man showed up, he had already agreed to pay for sex, and his arrival completed the offense
• They scheduled 'dates' every 30-60 minutes; at times multiple men arrived simultaneously, complicating logistics and requiring extra officers and transport overtime
Types of buyers encountered[47:50]
• Kara reports catching a doctor virtually every time they ran large stings at nicer hotels, including one man who arrived in hospital scrubs and another from a prestigious hospital
• At cheaper locations they often arrested tradesmen like cable installers and plasterers; she felt a bit more sympathy for them but stressed the crime was the same
• Almost all buyers were married and begged officers not to tell their wives; many also specifically requested sex without condoms ('bareback'), raising concerns about disease risk to their families

Notable buyer anecdotes

Nervous younger man trying to get his wife pregnant[49:00]
• One man in his 30s refused to go to a hotel room and insisted on meeting at the hotel bar; when officers arrested him he fainted and later cried, telling Kara he was anxious and trying to get his wife pregnant
• She pointed out the recklessness of attempting to conceive while simultaneously seeking unprotected sex with a stranger, potentially bringing infections home
Northeastern professor and bargaining[49:47]
• A Northeastern University professor tried to haggle down Kara's stated prices, saying he did not make much money, and requested 'yoga positions' and 'aggressive kissing'
Wealthy philanthropist who laughed[50:10]
• Another buyer was a diminutive, bespectacled multimillionaire philanthropist from Beacon Hill who sat on children's hospital boards; upon arrest he laughed and seemed unfazed
• He paid his fine, focused primarily on regaining his phone, and later met Kara at a Fenway Park detail to retrieve it, joking that relationships were 'not worth the trouble'

Economic and safety realities for prostituted women

Pimps taking nearly all proceeds[50:35]
• Kara emphasizes that about 99% of the women she encountered did not keep any of the money; pimps demanded every dollar and often used violence to enforce control
• Only one woman she met-a specialist in 'sissy play'-appeared to work independently and keep her considerable earnings (e.g., $500 an hour), which Kara and a colleague jokingly viewed as a possible post-retirement job
Violence and coercion behind the transaction[51:40]
• She told arrested buyers that their payments did not create a victimless exchange; many women were beaten, controlled, and deprived of money and identification by pimps

Pornography, fetishes, and skewed sexual expectations

Pornography's effect on intimacy and buying sex

Skewed expectations from porn consumption[52:15]
• The host argues that starting sexual experience with pornography can skew expectations, as it allows people to 'type in exactly what they want', making real intimacy more difficult
• He suggests some men may seek prostitution as an attempt to recreate porn-like control in real life, specifying 'search terms' via code words and money
• Kara notes that prostitution is ancient but modern access to porn and on-demand services may change how people relate to it
Nonconsensual porn and moral concerns[53:05]
• The host references an earlier guest who asserted that much online pornography is nonconsensual, meaning viewers may unknowingly be watching actual crimes
• They both highlight the depravity of a system in which exploitation may be consumed as entertainment without viewers' awareness

Fetishes and odd requests encountered

Code questions and specialty requests[53:35]
• One buyer coyly asked if she spoke any languages, expecting her to reply she spoke 'Greek and Russian', coded for specific sexual acts
• She tried to attract foot fetishists by including her feet in photos because many callers had strong foot preferences
Unusual fetish example from her life[53:24]
• The host mentions a friend who hired a woman to tickle him until he defecated, illustrating how specific and extreme some fetishes can be
• Kara wonders aloud how such fetishes develop, speculating about experiences in childhood that might link bodily functions and arousal

Major multi-year human trafficking investigation

Case origins and early leads

Hospital call about a raped minor[55:15]
• A three-year investigation began when Children's Hospital in Boston notified them that a girl (around 15-16) reported being raped in Rhode Island
• The girl only knew her trafficker by a nickname and had a Facebook page; she also mentioned a female driver who took her to Rhode Island
Identifying associates through car and reports[55:43]
• A Homeland Security agent drove the girl around to locate the driver's neighborhood and spotted a red car matching her description, then ran the plate
• The registration led to a male name; Kara then searched police reports for that last name and linked it to a woman whose first name matched what the girl had given
• They assembled a photo array, the girl identified the driver, and investigators interviewed her, gradually mapping connections

Network of pimps and wide geographic spread

Hierarchy of two pimps and a violent boss[56:25]
• Two men initially identified as pimps in Rhode Island actually worked under a more dominant pimp who controlled many women across states
• The main pimp, in his late 20s, had around 11 'baby mamas' and 14-17 children, plus about 27-28 women he had trafficked over time
Mobility of victims and interstate elements[56:55]
• Victims were moved around extensively-to Maine, New York, New Jersey, California, and Las Vegas-often being driven cross-country to work and then driven back
• He was extremely violent, beating the women, urinating on them, and confiscating their shoes, licenses, and phones to prevent escape or contact with family

Pimp-on-pimp violence and prosecution

Shooting of subordinate pimp[57:33]
• When the main pimp suspected one of the subordinate pimps of cooperating with federal agents, he had someone shoot him in the head in New Jersey
• The victim survived with a 'piece-of-pie' shaped portion of his skull missing; he lost the ability to speak but could still sing songs like 'Happy Birthday' and the alphabet
Federal charges and lengthy sentence[58:10]
• Eventually the case went federal because of the interstate activity; the main pimp received around a 33-year sentence
• Kara says she was relieved when this long and complex case concluded and notes it was handled jointly with a Homeland Security Investigations agent who did substantial work

Awards and recognition for the case

Detective of the Year honor[58:22]
• Kara received a Detective of the Year award from the Boston Police detectives' union and an award from the Boston Police Foundation for this human trafficking case
Encounter with Mark Wahlberg and Peter Berg[58:55]
• At the Boston Police Foundation ceremony, Mark Wahlberg and director Peter Berg attended while promoting the film 'Patriots Day', and she took a photo with them

Police culture, relationships, and declining recruitment

Social circles and dark humor among cops

Preference for socializing with other officers[59:36]
• Kara says most of her social life was with other officers because they understand each other's experiences and share a dark sense of humor that might horrify civilians
• She maintained a small group of non-police friends from high school but often felt like a 'party trick' at gatherings when people asked for grisly stories
Closed-off holiday parties[1:00:20]
• For district Christmas parties she arranged, they insisted on private spaces rather than sectioned-off bar areas, joking that they were 'not fit for public society'

Relationships, divorce, and family structure

High rates of cop-cop relationships and strain[1:00:36]
• Spending 12-16 hours a day together leads many officers to date or marry colleagues; she notes this is common and can be easier because they understand the job
• Kara is divorced and says the job's long hours and exposure to trauma make it challenging for civilians to fully grasp an officer's mental state
Current family arrangement in South Carolina[1:01:15]
• Her ex-husband and his new wife moved to the Charleston area as well to be near her daughter; they get along and share family time, including with their younger child

Decline in police recruitment and public hostility

Drop in police exam participation[1:01:40]
• When she took the police exam, about 10,000 people sat for it; more recently, the department struggled to get even 800 applicants
Impact of George Floyd era and constant filming[1:01:55]
• She recounts how, after the George Floyd incident, officers were constantly filmed, cursed at, and sometimes spat on, while being unable to react
• Despite vocal hostility, she says many ordinary residents quietly appreciate and thank officers, even if they do so less frequently or loudly than critics
Views on National Guard deployment[1:02:35]
• Asked about using the National Guard in cities, Kara says it was 'great' when mayors failed to control chaos, and questions why some leaders opposed efforts to restore order

Retirement, relocation, and new pursuits

Move to South Carolina and climate preference

Choice of Charleston area[1:03:30]
• Kara moved from Boston to just north of Charleston, South Carolina, wanting to avoid cold weather but not wanting to live in Florida
• She appreciates nearby beaches such as Folly Beach, Isle of Palms, and Sullivan's Island and notes the area's beauty

Retirement benefits and decision

Pension structure and timing[1:04:15]
• Boston officers can receive up to 80% of salary after 32 years; Kara retired after 31 years with about 77% and felt ready to leave

New hobbies and creative life

Oil painting as a beginner[1:04:40]
• Kara has taken up oil painting, copying works by artists she admires to learn mixing colors and technique; she modestly calls herself 'terrible' and a beginner
• She also spends time at the beach and focuses on a more relaxed life after decades of high-stress police work

Closing reflections and gratitude

Appreciation for spotlighting 'normal' guests[1:05:10]
• Kara thanks the host for having 'normal people' like her on the podcast and expresses appreciation that someone cares about what police do
Host's closing compliments and gestures[1:05:25]
• The host compliments her appearance, thanks her and her daughter for coming, and arranges a dinner reservation for them, also thanking her for her service

Lessons Learned

Actionable insights and wisdom you can apply to your business, career, and personal life.

1

Real-world systems rarely match their media portrayals; relying on TV or online narratives to understand complex work like policing or investigations leads to unrealistic expectations and poor decisions.

Reflection Questions:

  • • Where am I subconsciously assuming that a movie, TV show, or social media portrayal reflects how something actually works in real life?
  • • How could I seek out firsthand accounts or primary sources before forming strong opinions about a profession, process, or controversy?
  • • What is one area this month where I will deliberately replace secondhand narratives with direct conversations or reading from people who actually do the work?
2

Exploitation often hides behind familiarity and emotional manipulation rather than dramatic, movie-style threats, so vulnerabilities in relationships and communities are crucial points to guard and support.

Reflection Questions:

  • • What kinds of emotional needs or insecurities make me or people I care about more susceptible to manipulation or grooming?
  • • How can I better recognize the difference between genuine care and someone slowly increasing their control or demands over time?
  • • Who in my network might be vulnerable right now, and what practical support or information could I offer them to reduce their risk of being exploited?
3

Systems that stop enforcing basic rules-like property laws or public order-rapidly erode trust and quality of life, showing that compassion and accountability must coexist in any healthy community.

Reflection Questions:

  • • In my own environment (workplace, neighborhood, family), where have I tolerated small rule-breaking that is now undermining trust or morale?
  • • How could I advocate for both empathy and firm boundaries instead of defaulting to one extreme (all punishment or all permissiveness)?
  • • What is one specific norm or rule I can help clarify and consistently uphold in my immediate circle over the next month?
4

Exposure to ongoing trauma requires intentional coping strategies-such as dark humor, strong peer support, or boundaries-to prevent cumulative stress from quietly destroying mental health.

Reflection Questions:

  • • What difficult experiences or stories do I carry from my work or life that I haven't fully processed or given myself permission to feel?
  • • Which coping strategies I use today are genuinely protective, and which might be numbing or avoiding in disguise?
  • • What is one healthy ritual (conversation, journaling, exercise, therapy, or creative outlet) I can add or strengthen to help me metabolize stress rather than just endure it?
5

Long, complex problems often require patient, unglamorous work-following small leads, collaborating across teams, and persisting for years-to achieve meaningful outcomes.

Reflection Questions:

  • • Where in my life or work have I been expecting quick, dramatic wins instead of committing to the slow, methodical progress that real change demands?
  • • How could I better break a big, messy problem I'm facing into smaller leads and checkpoints, like an investigator would?
  • • What is one multi-step project I'm working on where I can proactively strengthen collaboration with others instead of trying to carry it alone?

Episode Summary - Notes by Sawyer

#616 - Retired Boston Detective
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