This story was written several years ago.

Forty four years ago the world wept for John F. Kennedy whose life was snuffed out long before we had an opportunity to witness all the great things that he might have accomplished as President. Incredible as it may seem over four decades have passed in the blink of an eye and just about anyone who was old enough to speak at the time of Kennedy’s death can remember exactly what they were doing on November 22.

That day I wasn’t feeling well when I woke up and was somehow able to persuade my mother to allow me to stay home from school sick and was watching “Wagon Train” on television as the news of JFK’s assassination broke.

When the news bulletin flashed across the television screen I was angry that the show was interrupted until my mother explained the ramifications of Kennedy’s shooting. Hey, what did I know I was just a nine year old kid and after all being self absorbed and simply interested in my own pleasure made me exactly like every other kid on the block.

I still vividly remember the endless television coverage displaying JFK’s funeral procession, thousands of mourners lining Washington’s streets and paying their last respects at the Capitol Rotunda, and the heartbreaking vision of John-John offering a final salute to his father. A vision offered in grainy black and white images since a colored television was light years away from the Flanagan family home.

Like everyone else all of those images were available only on three or four channels and we were damn lucky to have them. A far cry indeed from the world of tv we know today.

Kennedy’s assassination was certainly one of the more momentous historical events to occur in 1963 but many other notable things also happened that year. For instance, the United States was growing increasingly more involved in Vietnam which of course ended up being one of our most unpopular, divisive wars tearing us apart at the seams and dragging on for years with a staggering loss of life.

1963 was a defining moment in the Civil Rights Movement and the events of that year brought the inequities suffered by African Americans to the forefront of America’s consciousness. President Kennedy had proposed the Civil Rights Bill to Congress, civil rights leader Medgar Evans was murdered and four young black girls died in a church bombing in Birmingham, Alabama.

On August 28, Martin Luther King led a March on Washington in support of Kennedy’s bill and delivered his memorable “I have a Dream” speech before hundreds of thousands. Following these events people began to mobilize against segregation leading to the 1964 passage of Kennedy’s Civil Rights Bill.

Yes, unforgettable historic events dominated the world stage in 1963 but that same year my classmates and I made history in our own right by becoming the first third graders admitted into the brand new Warren Prescott School. By June the school year ended and following a wonderful summer respite Ms. Martin’s former third graders returned to school that September, a bit older, wiser and ready to buckle down as fourth graders assigned to Ms. Harrington’s class.

At the start of the school year I was just a nine year old kid celebrating the recent birth of my baby sister Patsy but by year’s end had also experienced true love for the first time. The kind of love that touches you to your very soul and stays with you forever. I can’t quite recall where she came from but before I knew it an angel had descended into Ms. Harrington’s classroom to watch over us.

She certainly had an odd name but our student teacher, Ms. Gissandanner was beautiful, or as my sons might say, she was “hot”. I loved Ms. Gissendanner and after meeting her the hours seemed to fly by and none of the boys had to be told twice to listen and pay attention. How could we not listen and pay attention?

We were mesmerized by each and every one of her magnificent words. After all, young minds consumed by baby sisters and thoughts of love and lust for their teacher simply had no place for thinking about things like dead presidents, the Cold War, soldiers dying in faraway jungles or bombed out churches. As the school year progressed the days melted into weeks and before long we learned that Ms. Gissendanner would be leaving us.

I remember standing in the hallway with several of my friends, watching one of our classmates weeping openly after hearing the devastating news. I have often wondered what happened to Ms. Gissendanner and thought about trying to find her but was concerned that someone would accuse me of stalking the woman.

Forty four years is a long time but I figure perhaps one day Ms. G and I will meet again. I would love to hear her beautiful voice once more and tell her how much she meant to the students in Ms. Harrington’s fourth grade class and how she saved them from the crazy world around us.


I wrote the article below several years ago when the debt ceiling debate was all the rage in Washington. D. C. Then I got to thinking about technology-the net, smart phones, social media etc so recently added a bit of information at the end beyond the issue of the debt ceiling. At a later date I may revisit this issue and focus less on the debt ceiling and expand but view this as a starting point. I truly believe we are suffering from information overload and it is troubling to me on many levels.


Pundits recently offered varying opinions about whom they thought benefited from the debt ceiling debate and debacle and came up with diverse responses including the Democrats, Republicans-Tea Partiers, Lobbyists, Wall Street fat cats, and even gasp, the people.

I’m not quite certain yet exactly who won the debate but I think social media, transparency and public participation definitely emerged as winners. That’s great news for the democratic process. But, are we better off because of it?

Transparency, social media and public participation won and while certainly welcome and refreshing will likely vex the lawmaking, deal making process forever by compromising it-intruding if you will, in a process long conducted somewhat behind closed doors and off the radar screen of many.

The lobbying process has been around for a long time but most of the work has been conducted behind the scenes as elected officials responded to various opinions, interests and political pressures to work the kinks out of an issue or legislation for better or worse depending on your perspective.

We all know there are countless “lobbyists” and recognize that the process that takes place will eventually end up benefiting some at the expense of the rest.  Lobbying isn’t a bad word and just about anyone can “lobby” on a given issue that they are passionate about and believe in it’s simply a very competitive, often frustrating, lengthy process.

Regardless, most of the time the process of lobbying is a long, complex one that involves passion, research, compromise, horse-trading, face-saving, reputation enhancing or whatever it takes to get the job done. A process that like it or not is by its very nature prone to being influenced by money, power, perceptions among other things.

Typically, public involvement has been in the form of meetings, phone calls to talk shows, letter writing, emailing, group visits to Congress, state level legislators, municipal officials. This was/is an often very slow vetting process prone to abuse, delays, unpredictable issues, ideological differences, complications, “politics” or even the whims of an elected officials’ staff as to whom to schedule and when.

Now, thanks to the growing influence and use of social media and the mandates for greater  transparency everyone- The Prez, Congressmen, the media, inmates, illegal immigrants, kids, housewives, students, foreigners,  terrorists, whack jobs, indeed everyone and anyone may be potentially be openly involved in the day to day process.

We’re constantly face booking, tweeting things about the process, legislation, who said what to whom every second. This hands on citizen process and involvement truncates the lawmaking, vetting, deal making, compromising process. While this is a great step towards a truly democratic, open process the potential for slowing it down and clogging up the system is great.

At the same time our form of government was created to allow us to elect others, to represent us in DC, at the State House in City Hall so we can go about the business of living our lives.

Today, the process of governing is becoming so transparent and immediate and in our faces that some of our leaders are afraid to take action, make decisions without being quoted, tweeted, castigated, and praised and it is making the lawmaking process even slower than the norm.

The increased transparency, social media and citizen involvement are positive of course because it puts our leaders on notice and in theory the “people” may/should benefit by knowing what is going on and who benefits from legislation. I fear the process may grind to a halt as individuals get more involved in the day to day details of legislating and politics and horse trading we know little about.

For instance, before the emergence of the debt ceiling crisis how many of us knew or even cared what it is, what is involved, and so on.  After all many of us are too busy looking for jobs, housing, affordable health care, food stamps to focus. Otto von Bismarck supposedly said we should never see sausages or laws being made and perhaps he was right on the money with that sentiment.

Can you imagine what the 55 members of the Constitutional Convention who gathered to sign off on our Constitution might have said, written, agreed upon if the public-the world had been involved? Back then 55 men signed off on the Constitution but the debt ceiling issue may have involved as many as 55 million trying to influence it, who knows? Do we really need to be involved in every decision that happens in Washington D.C, state and local government or do we have other things that we should be more concerned about?

In the 1770s’ news, political changes, presumably everything took forever to travel from the East to the West Coast and who knows how long to reach say Asia so there were far less implications, reactions good, bad or indifferent. Even back in my early days news reports about early space travel, election results, casualties in Viet Nam, and natural disasters a world away were transmitted to us if at all through grainy B & W TVs or transistor radios.

Communications tools and technology including computers, smart phones, the internet and social media among others have brought us closer together and helped us to stay in touch and make positive contributions to society. For instance we can now stay in touch with long lost family and friends even though we may never see them in person preferring instead to communicate from our homes, offices or even bathrooms.

Last year’s ALS Ice Bucket Challenge which found people from around the world dousing themselves with ice and challenging one another to do the same raked in millions to help battle the devastating ALS disease. In another instance a woman in desperate need of a bone marrow match for a family member used social media to find one presumably saving her spouse from death.

However, along with the good that technology has brought I believe we are inadvertently (and I daresay at times intentionally) stressing one another out, angrily taunting and insulting one another from afar because the net and social media have enabled us to do so seemingly without retribution. If someone posts a story or picture about anything good or bad, there is going to be a guaranteed response regardless and sometimes it is nasty, biased or include language and imagery that should never be shared.

This does not even take into consideration the fact that terrorists, serial killers, animal and child abusers, ISIS whack jobs, crazed world leaders and others can establish facebook and twitter accounts. These individuals can then gain privileged information about trade secrets, security measures, develop bombs and easily assimilate with others thanks to information available and earn their 15 minutes of fame or infamy- AND WE ARE ALL HELPING THEM TO DO SO AND PERPETUATE THEIR MADNESS.

We have become a world of individuals who are too dependent and obsessed with information that may or may not have any bearing on our day to day lives and while it may be useful, informative and life enhancing it is making us crazy. There is much more that can be said about this issue and I am hopeful that I have sparked debate and caused you to think a bit more about it.

What Christmas is all about. Helping one another

David Flanagan

As the holiday season approaches I thought of sharing the following piece. I wrote the story about twenty years ago when my kids (and I) were much younger. I decided to leave it unchanged from the original despite editorial changes I would make now if rewriting the story.

The story appeared in various local newspapers on the editorial page and I think my angst over being able to provide for my children as a parent then is perhaps even more true for many now given the current economic climate.


Over the past few months, we’ve been continuously bombarded by an endless flow of advertisements from merchants heralding the arrival of the holiday season and announcing the availability of their products.

Of all the merchants hawking their wares and urging us to spend our hard earned dollars, perhaps none are as persistent or potentially influential as those who represent the toy and games industry. Television commercials, full-page newspaper ads and glitzy flyers all implore us to do one thing-run out to the nearest mall ASAP and pick up as many items as possible in time for Christmas.

Have I been affected by their pleas? Of course, toys and games are loads of fun, and after all don’t I have two kids at home who are anxiously awaiting the arrival of Santa? Let’s face it, the advertisements have worked or shall I say the arm twisting has been extremely effective. I mean, what type of father would I be if I didn’t do everything in my power to make sure that the kids are amply rewarded with as many toys and games as possible? Talk about guilt feelings!

So recently I found myself at the Independence Mall among hundreds of other parents, grandparents, aunts, uncles and other would-be Santas joined in the quest for the ideal gifts. As I wandered down aisle after aisle of bikes, games, dolls, Playstations and stuffed animals I found myself simultaneously awed and disheartened over the exorbitant cost of toys today.

Forty dollars for a not-so-cute doll, fifty bucks for a Legends of Wrestling videogame, $130 for My Size Barbie as Rapunzel and $250 for the Star Wars 25th anniversary LEGO Imperial Star Destroyer.

As my journey continued I experienced tremendous feelings of ambivalence toward the holiday season. On the one hand I was thrilled at the thought of being able to purchase gifts for the kids and witnessing the pleasure that such items would surely bring. Conversely, I felt great concern and guilt over whether I would truly be able to afford enough gifts to ensure such pleasure.

At the same time, I began thinking about other parents who, as a result of the current economic climate, may not have the wherewithal to feed, clothe or house their children, never mind smother them with gifts. What does a single mother tell her child on Christmas morning when the boy rushes over to their tree and finds that there’s nothing beneath it?

How does an unemployed father answer a child who asks, as tears well up in her beautiful blue eyes, what has she done that was so wrong, so terrible that it could cause Santa to abandon her this Christmas? What crosses a little boy’s mind when he visits his friend’s house and notices a mountain of toys and games heaped beneath the tree?

While thinking about these questions I found myself drifting back to my own childhood and recalling Christmases past: the annual Christmas Eve ritual of leaving out hot cocoa and cookies for Santa and carrots for his reindeer, my sister and I opening our gifts and the family gatherings at Nana’s home in Dorchester.

How wonderful those Christmases were and how fortunate I am to have such pleasant, enduring memories of them. Yet, while my Christmas memories are indeed positive ones, there were several that may not have been quite so enjoyable had it not been for the generosity and compassion of various charitable organizations and their contributors. Charities and Good Samaritans that come to mind include the men and women who threw the annual Christmas party in the Charlestown Navy Yard, Globe Santa in Boston, Scituate Community Christmas, the Kennedy Center and Townie Santa, and the Salvation Army among others.

Unless you have been fortunate to have received assistance from one of the many charitable organizations that exist I’m not sure that you can ever really appreciate how wonderful a service they provide to their recipients. Such organizations and the volunteers who support them truly embody the spirit of Christmas and can make a profound difference in the lives of those dependent upon them.

Think about it-total strangers coming together, giving of their time, money and energy to help make life a bit more bearable for people whom they may never meet. That to me is truly what Christmas is all about.

Has Christmas become too commercialized and focused on material pleasures and the temporary satisfaction that showering one another with gifts during the holidays brings? Yes, of course it has and in reality there is so much more to Christmas and the holiday season such as getting together with family and friends and celebrating how much we mean to one another. It also means reaching out to help someone in need and trying to bring a smile of joy to those we encounter in all that we do.

Like most parents I have always tried to instill within my children the same strong values of honesty, compassion, hard work that my mother provided to me by way of example.

However, my point here is that when your kids are young you simply have to try to find the right balance of making their wishes for material things come true until such time as they’re mature enough to realize there is so much more to Christmas morning than finding a pile of gifts beneath the tree. Sure, many never mature to the point where they acknowledge that there is more to life than just self satisfaction but that is a story for another day.

A neighbor informed me that she doesn’t support Christmas only-oriented charitable organizations since she believes it is inappropriate to focus on helping kids one day a year while ignoring their plight for the other 364 days. I can understand the point that my friend is trying to make; however I totally disagree with her. Yes, of course we should try to help one another each and every day of the year. Unfortunately, however, there’s really no way that we’ll ever be able to fully eradicate the poverty, hunger and hatred confronting mankind, nor ease the pain and suffering that people, particularly our children, are experiencing with an ever-growing frequency.

The least that we can do is to try to brighten up their day and bring a smile to their face around the holidays when they might otherwise be forgotten.

To those who can afford to put a little bit of money or time aside I would ask that you consider making a contribution to one of the many Christmas charitable organizations that work tirelessly to ensure that no one is forgotten during the holiday season. I can assure you that your compassion and consideration will be appreciated and never, ever forgotten.


Flanagan & Associates


Flanagan & Associates is an independent consulting firm offering government relations, community outreach, business development & grassroots public affairs capabilities to municipalities, political candidates, & corporations. Our team assists clients by facilitating meetings w/key decisionmakers & cutting through bureaucracy in all sectors saving valuable time, money & resources.

David Flanagan offers extensive experience in state & municipal government, private industry, nonprofits, unions, insurance, construction, transportation, corrections & trade associations. Flanagan has vast experience in political campaigns for candidates at every level of government.

An experienced communications professional Flanagan’s experience includes four years as director of business development for Road to Responsibility (RTR), a nonprofit supporting disabled adults.

Previously, he served as manager of community/government affairs for the MBTA & community liaison during the MA DPW’s $300M Central Artery North Area Project.

His background also includes serving as director of business development for Carlin Insurance & as government relations director for Associated General Contractors of MA.

Flanagan, has a BS from Boston State College & a master’s degree in public administration from Suffolk University’s Sawyer School of Management. He is a former staff director for Boston City Councilor Maura Hennigan & director of special projects/neighborhood liaison for the Office of Neighborhood Services under Mayor Ray Flynn.

Originally interested in pursuing a law enforcement career Flanagan served as a Deputy Sheriff/Jail Officer at the Charles Street Jail in Boston (now Liberty Hotel) for four years after graduating from college.

In addition, Flanagan serves as Lead Case Manager for RTR providing leadership to a team responsible for the support, evaluation & treatment of developmentally & physically disabled adults in group residential settings & is MAP (Med Adm) & CPR certified.

Recently Flanagan began working with New England Village, a community located in Pembroke, MA that serves adults w/intellectual & related developmental disabilities.

I wrote this article five years ago and have not edited it in some time. As much as the internet, social media and related technologies have been a boon to civilization I also believe it is having an increasingly negative impact. Now we can no longer live our lives in ignorance since we are constantly deluged with info we have little control over. Information is great if we take action but if we just post about it and simply spread the message what are we really accomplishing?


Why do employers fear social media and ban or limit their employees from using it during work hours? Do employers have a valid concern about social media use by employees and do they have the right to limit or ban its use? Will Executives over 50 ever get Social Media and why do many resist embracing and promoting it?

I’ve seen these and similar queries posed as more and more news stories break about employees using or abusing social media outlets while ostensibly working. Granted there is a valid place for social media and a need for it to enhance an organization’s communications abilities or reach. However, I believe employee use must be monitored during work hours and guidelines implemented concerning what is communicated by whom and when, where and why.

Common sense and respect for the rights of others should prevail when it comes to the use of social media but in reality some individuals simply lack such traits. Employees must be educated about what types of information should be transmitted regardless of whether it is during work hours or after hours when it relates to their employer.

For instance, should a hospital employee be able to post patient information or photos on Facebook? Should an employee working in corrections display pictures of an inmate’s cell online? Is it reasonable for an employee of a company providing supplies to the US Department of Defense to discuss contracts or display pictures of prototypes?

I appreciate social media and embrace all it has to offer but also believe it is simply one more tool (albeit a powerful one) to be used to communicate effectively along with the more time tested, traditional methods. As such, I wanted to offer my own humble opinion about why there may be reluctance on the part of some to accept social media and all it has to offer if used judiciously.

Many executives or individuals in their 40’s, 50’s, and 60’s are used to working in an environment that is very private, personal and reserved. Those who are even older remember wartime slogans such as “Loose lips, sink ships” and are concerned about indiscretion out of concerns about privacy, confidentiality breaches, reputations, decorum, trust, lawsuits and so much more.

In this era of increased reliance on new technologies, ever changing communications channels and greater transparency the ability to develop and maintain trust is perhaps more important than ever before as we struggle to keep things in check.

At this point corporations, government agencies and individuals should be gravely concerned with how much information should be shared online and otherwise and with whom. As a business owner do you really want to do business with an organization or agency whose employees openly discuss your business, contracts, staff, and profits online?

The ability of workers engaged in confidential work activities to note their every movement (via Twitter, Facebook, Linkedin et al) and post pictures of their work site or seemingly private after hours proclivities is terrifying to many business owners since it can cause their clients to lose faith and trust in them among other things. So while it is important to develop ones online brand and identity to effectively compete it is similarly necessary to preserve trust above all else.

When I first got involved in Boston politics and organizing political campaigns I remember the older activists suggesting that one should abide by a “Code of Silence” such as that attributed to Marty Lomasney, Ward boss of Boston’s Ward 8 regarding the need for discretion.

Lomasney, who served Boston as a state Senator, Representative and Alderman may best be remembered for allegedly saying that when it comes to discretion “Never write if you can speak; never speak if you can nod; never nod if you can wink.” Today, that quote could probably be updated by adding “never put it in e-mail, text it or post it to Twitter, Yahoo, Facebook, Linkedin” and on and on and on.”

The advent of things such as the internet and cell phones while incredibly useful have enabled people to easily share information about themselves and conversely learn more about the other person. In many cases this has led to privacy invasion, identity theft, embarrassment because of past/current transgressions that suddenly become fodder for gossip etc. Then of course misuse can also lead to other events such as claims of libel, slander and potential lawsuits.

I think perhaps many erroneously believe that branding and creating or preserving one’s reputation somehow just materialized over the past few years due to the internet and social media.

Senior executives are used to doing business privately and maintaining a reputation as being staid and creating a brand that buyers and the creators themselves could be proud of and believe in. Think IBM, Sears, Ford or any of the millions of iconic businesses that have been around forever or finally merged or collapsed after many, many years of successful operation.

Of course then there are issues of competition and concealing company secrets from competitors out of a desire to be successful and make a profit and maintain patents from infringement and theft.

Think of corporate or government communications for instance. Generally there has been one department, team or individual responsible for publicity, marketing, or otherwise spreading good news and minimizing the bad. Requests for information have generally been channeled via the department, team, and individual so everyone is on the same page.

If a crisis or incident happens in a government agency or say a hospital historically there has been a crisis communications plan with one, unified voice to protect the interests of the institution and those involved. To many executives social media is viewed as being unrestrained and loose since conceivably everyone within the organization can “discuss” every minute detail of a crisis to the “world” instantaneously.

Today in our age of sound bites and immediacy-information sharing that is unfiltered, too personal or overly transparent can be cause for concern to many older and younger individuals alike.

This includes revealing every private moment about ones life, love life, sexual escapades, what they had for breakfast, how much alcohol they had to drink the night before or any other event that people like to talk about seemingly without reservation. It seems like only yesterday people would say “that’s way more information than I need to know” if you provided them with too many intimate details about your life.

Its one thing for individuals to tweet about themselves, reveal secrets about their lives and loves on Facebook, Linkedin or any other venue but quite another thing to share such items or confidential corporate information especially while ostensibly working.

To many executives such activities while useful in extolling the virtues of an organization can be viewed as potentially damaging to one’s brand and time consuming and wasteful. This is especially worrisome to executives if it is done haphazardly, consistently, illegally or in a manner that causes libel, slander of injury to another.

It’s incredible how much information some are willing to share with the world. Some individuals cherish their privacy and have a greater sense of privacy, decorum and tastefulness than others who seemingly seek to tell the world about every event in their lives. Think sexting and sharing pictures of oneself nude, drunk or engaged in what should be private pursuits via a cell phone, net, Instagram and on and on.

I’ve personally come a long way concerning what I’m willing to share. Social media obviously offers tremendous benefits but many believe it should be prudently used in the work environment since so much is potentially at stake. I agree.


This piece appeared in The Boston Metro free paper several years ago and a recent discussion and visit to the Liberty Hotel sparked fond memories of my first post college full time job in law enforcement.

I stayed at the Liberty Hotel in the old Jail section in February 2009 , stayed again in 2010 , frequently visit for dinner and drinks and it is always awesome to return over 25 years after leaving the building as a Jail Officer for the last time.


During a recent visit to Boston I passed by the former Charles Street Jail and was amazed by how much it has changed since the decision was made to knock down part of the structure, expand the Massachusetts General Hospital and build a hotel on the site. The Charles Street Jail designed by noted architect Gridley J. F. Bryant and built in 1851, was home to thousands of pre-trial and sentenced detainees who passed through its portals before they closed permanently in the 1980’s.

The MGH expansion project has several components including the dismantling of the Jail’s East wing to accommodate the construction of an underground garage and 400,000 square foot Ambulatory Care Building. Another element is the erection of a 220,000 square foot building for outpatient surgery. Part of the Jail will be restored and anchored to a 300 room hotel and conference center being built by developer Dick Friedman. In addition, the Charles Street MBTA station will be renovated.

I was intrigued by the project because of my own personal history with the jail, the MBTA where I was employed until recently as the Manager of Community Affairs and the MGH. As a child I made an inordinate amount of trips to the MGH thanks to various illnesses, broken bones and operations. On each occasion my mother and I would walk past the Jail en route to the adjacent hospital and I always wondered about what was going on within the confines of that imposing granite structure.

What manner of individual could possibly be housed within such an immense fortress surrounded by enormously high walls adorned with razor sharp barbed wire, I would ask. “Criminals live there my mother would explain” whispering as though they might hear. Little did my mother or I realize at the time that her son would one day end up behind those seemingly impenetrable walls.

During the four years I “served time” at the Jail I witnessed some extraordinary situations and had a number of experiences that will stay with me for the rest of my life. One of the most frustrating circumstances the guards would encounter were certain reform minded policies and civil libertarians who catered to the inmates as though they were guests staying in a five star hotel. Little did we know that there would one day be a top notch hotel situated on the site.

During my tenure some of the most notable detainees whom I encountered were those awaiting trial for numerous spectacular and well publicized crimes including the massacre at the Blackfriar’s Lounge, the slayings at the Sammy White Bowladrome and the Suffolk County Courthouse bombing. Other detainess include those accused of the rape and murder of a young nurse on Commonwealth Avenue whose last frantic words were captured on a 911 taped call and the trio arrested for the killing of a popular Harvard University football player, killed in Boston’s Combat Zone.

While I was employed at the Jail there was an unyielding public discourse about the jail and whether it was fit for human habitation.  Lawsuits, civil liberties actions and prison and jail reform movements eventually led to the requirement that jails and prisons be cleaner, more modern, more humane places of detention.

A 1973 U.S. District Court case was the impetus that led to the decision that a new jail must be constructed in Suffolk County. In U.S. District Court case Civil action #71-162-6 Inmates of the Suffolk County Jail et al vs. Eisenstadt (Sheriff), the Charles Street Jail was found to be “unfit for human habitation”.

In this instance the Court found that the quality of incarceration at Charles Street to be “punishment of such a nature and degree that it could not be justified by the state interest in holding defendants for trial”.  It should be noted that a key element in the Court’s decision in this case is that a jail is a place for the detention of “pre-trial”, and thus presumably innocent individuals, as opposed to a prison, which is a place for the incarceration of those found guilty of a crime. That Court decision led to the closure of the Jail and the move to preserve the historic granite edifice which ultimately led to the brilliant MGH plan.

It is quite interesting to think about Charles Street and its prominent place in Boston’s history and visualize how it will look once the current construction project has been completed. Imagine that one day hotel guests will pay top dollar to stay on the grounds of a facility that formerly housed many of the states’ most notorious criminals in a setting deemed “unfit for human inhabitation”.








By David Flanagan

There he was, propped up against the dark, rusty, cold metal stairwell on the second floor of 160 Bunker Hill Street in Charlestown’s Bunker Hill housing projects. “Davey, can you help me? Can you take me home?. I looked and realized that it was Jim, one of my neighbors, father to several of my friends. Jim, who must have been in his 30’s or 40 tops, was lying there, legless, totally out of it, less than a quarter mile away from his apartment, his wife and five kids. What does he want with me, I thought?

“Davey”, he cried out. I looked at his hair, which seemed to be desperately trying to escape from under his scalley cap, his sun browned, wrinkled face and tired eyes trying to focus on me. “What do you want, Jim?” I asked, more irritated than patient at his calling me. I felt bad for Jim. This wasn’t the first time that I had seen him, legless, filthy, roasting under a fog of alcohol, asking for some change, a handout, a little conversation perhaps.

It seemed that all Jim wanted from me this time was a lift home. Except in this case, a lift home would be one traveled upon the shoulder of an embarrassed, shy twelve year old. “Come on Jim” I said and helped him from the stairwell. “Put your arm around my shoulder Jim, you’re heavy” Embarrassed, I prayed to God: please don’t let anyone see us limping along or they’ll think he’s my father.

I felt a thousand eyes upon us as we approached Carney Court. Dozens of kids playing out in the warm, summer sun. How could I have thought that our journey would go unnoticed. Stumbling along, moving much slower than I could bear, our trip lasted a lifetime. What if his kids see us, after all Billy and I shared a class at the Warren Prescott and brother Bobby was also a friend. Please, God let this ordeal be over soon.

As we walked across O’Reilly Way, Jim’s arm slipped from my shoulder and we almost fell into the street. My grip held, I propped Jim up and we continued, knowing that relief was only several hundred feet away. But, soon I could see Billy and he saw us.

My mind soaked up the look on Billy’s face with each step as his father and I drew closer, walking arm and arm toward him and our friends. Billy walked over to us and said “thanks Dave” and without saying a word to his father, relieved me of my burden and my shame. I walked away, head down, embarrassed about being seen with Jim and having to deliver him to his son, my friend in that condition. My shame and embarrassment could only have paled in comparison to that felt by Billy and his family.

Over the next few years there would be many other episodes involving Jim and his losing battles with the bottle and self-respect. Battles where there were clearly no winners, only losers. Jim passed away several years later from cirrhosis, but his pride, his will and his family’s hopes died long before he did. Several of Jim’s children ended up involved in violent crimes and were imprisoned in various prisons across the US.

I wonder how different things might have been if Jim had been able to hold a job, behave like a husband and father should, find his way home and win his battle with the bottle. The losing battle that Jim and his family waged against alcohol was fought by many of us in the projects. Unfortunately for Jim and his family, their losing battle with alcohol was a very public one with tragic consequences. For some the battle was far less public but in many cases the results no less tragic.

The story above is true but the names have been changed to maintain privacy and will never be revealed.