Condo living on the Gold Coast: Lawsuits, ﬁnes, insults
21 July 2017
building at 111 E. Chestnut St. in Chicago’s Gold Coast neighborhood
has has been the scene of some tumultuous clashes resulting in
lawsuits. (Terrence Antonio James/Chicago Tribune)
Inside an austere Gold Coast tower overlooking North Michigan Avenue,
the condo board president allegedly charged at a gadfly board member
during a meeting and drew his fist back in rage.
No punch was ever thrown in that 10th-story conference room, but
Chicago police investigated, witness statements and affidavits were
taken and misdemeanor assault charges were filed and later dropped.
Like many of the tales of dysfunction inside the building where the
city's only female mayor once lived, the exact nature of what happened
is disputed, but it allegedly started with numerous angry emails —
including one with a photo of an extended middle finger — and a shouted
expletive at the meeting.
The 2011 incident seemed to open the legal floodgates. Residents and
board members have filed numerous lawsuits since then, and some have
dragged through the courts for years.
While plenty of Chicagoans can share war stories about their condo
associations, this battleground in the 100 block of East Chestnut
Street may be in a class by itself. The condos are high-priced — some
marketed at upwards of $800,000 — but the issues have often been petty,
from blog posts to remarks made on the elevator.
A disgruntled homeowner sued after being fined $500 for allegedly
making obnoxious comments to building staff; that same resident also
allegedly exposed his nipples to staff and left the fly on his pants
open. Another resident sued after he was booted from the condo board,
alleging the board president sent out a defamatory letter that led to
his ouster. And the board president sued right back for an allegedly
defamatory blog that compared the president, a suburban dentist, to
North Korean dictator Kim Jong Un.
who has been in disputes with his condo board, says he loves living in
the Gold Coast building, with its prime location and views, and that he
isn’t going anywhere. (Abel Uribe/Chicago Tribune)
In 2014, the blog's author was charged with a misdemeanor count of
electronic harassment after allegedly claiming in an email to residents
that the condo board president had rigged a board election. Cook County
prosecutors later dropped the charge.
The founder of the blog is Brian Connolly, a former PR executive who
was twice kicked off the condo board. He says he fears he may lose his
home if a Cook County judge agrees to award more than $130,000 in
attorneys' fees to the board. But he has no regrets.
"Egos — it's egos," said Connolly, who called his long fight with the
condo board "righteous." He posts his blog on what the board president
claims was once the association's web domain – another disputed detail
that Connolly denies. "That was it. They wanted me out."
"Where do I think it ends? If the judge comes back and says, 'You owe
them $130,000,' I'm more than confident that they'll try to take this
place," Connolly said. "So with fighting over a $1,000 fine I will have
lost my condo. It's unbelievable."
Milazzo, president of the condo association at 111 E. Chestnut St. in
Chicago and owner of a condo there, also has a home in St. Charles. He
expects to have his first child this summer and plans to step down from
the association when his term ends next spring. (Stacey Wescott/Chicago
Another combatant, a successful BBQ restaurateur and property manager,
told the Tribune he moved out of the building and sold his unit rather
than risk an eighth heart attack. And the current board president,
Anthony Milazzo, who expects to have his first child this summer, plans
to step down when his term ends next spring.
Milazzo said Connolly, in particular, has filed so many lawsuits that
the association's insurance carrier dropped them and the new one
quadrupled premiums, set a $100,000 deductible and excluded coverage of
any Connolly litigation.
"He has the ability to cause trouble in a way I've never really seen before," Milazzo said.
"It was out of control," said board member Serap Brush, a UIC professor
Milazzo recruited to the board, in a deposition for one of the
lawsuits. But another board member, Asia Gajderowicz, said in her
deposition she noticed "prejudice" in fining residents who didn't fall
into line behind the board president. She didn't specify who was
Tens of thousands of Illinois residents live in condos, and the
homeowners associations that oversee the properties are a
billion-dollar business, attorneys in the field say. There are constant
legislative and legal battles over what power those associations can
exercise and what rights residents have.
Experts say emotions can run high in condo disputes both because of
what's at stake and because the battle is often lopsided: The board has
much more power and also nearly unlimited legal resources. Residents
are passionate about defending their homes while boards are fearful of
ceding power as they pursue their vision of the greater good.
"The reason I find that it's so emotional is it's their homes and
there's a lot of emotional attachment to where they live and what they
do," said Norman Lerum, an attorney who has long included condo
disputes in his practice and who represents Connolly along with a
Interviews, depositions, blog postings and thousands of pages of court
records reveal the level of dysfunction at the 56-story building, on
prime real estate between a Bentley dealership and Water Tower Place
that Jane Byrne, the city's first female mayor, once called home.
One lawsuit filed by another owner against the condo board over a $500
fine for allegedly "obnoxious" remarks — as defined in the condominium
rules — has now spanned four years. During that time, a half-dozen
residents were deposed and elevator security camera video was
scrutinized and debated like Zapruder film footage to determine whether
a resident had been rude to a building employee.
The association has spent hundreds of thousands of dollars in legal
fees and includes a line item in its budget for lawsuits filed by
Connolly, who says he only sued to protect his First Amendment rights.
He has spent tens of thousands of dollars suing the board, sometimes
The board settled a defamation lawsuit he brought over a letter written
by Milazzo, signed by three board members and sent to residents that
called Connolly "unfit to serve on our board." Connolly says it
resulted in more than two-thirds of homeowners voting to boot him off
Connolly also successfully fought off a lawsuit filed by the board
president over his blog that compared Milazzo to North Korean dictator
Kim Jong Un and corrupt politicians like autocratic former Louisiana
Gov. Huey "Kingfish" Long.
On his blog, Connolly quotes Louis Brandeis on the disinfecting power
of openness and includes photos of Mahatma Gandhi and Martin Luther
King Jr. beside the quote "No one has ever changed the world without
first being labeled a troublemaker." Much of his blog's outrage is
directed at more mundane topics like hallway restoration work, board
meeting recaps and condo sales figures.
Still, Connolly, with more than three decades of experience in public
relations, knows how to draw an audience — and get under the skin of
his adversaries. He told the Tribune in an interview that he was behind
the blog Strumpette — a behind-the-curtains blog about the PR industry
that drew a write-up from The Washington Post's media columnist in
2006. Connolly posted as "Amanda," described on the blog as "5' 4"
tall, athletic, Pantene shoulder-length black hair, perfect perky
An appellate court recently upheld a Cook County judge's ruling that Connolly's condo association blog wasn't defamatory.
Connolly hasn't always succeeded in his quests. He filed a lawsuit in
2013 challenging $1,000 in fines imposed by the board over his
allegedly confrontational admonitions to people in the building —
including telling pool users not to use glass drink containers. A Cook
County judge dismissed the lawsuit and found Connolly made frivolous
arguments that were deserving of sanctions. The judge has not yet ruled
on what they will be, though the condo association has asked for more
than $130,000 in legal fees.
Milazzo said Connolly's efforts have, in many ways, backfired.
"It got to the point where it was so toxic nobody wanted any part of
it," he said. "The irony of it is that all of Connolly's attacks only
empowered me, because nobody wanted to take the (leadership) position."
Connolly isn't the only former board member enmeshed in legal battles
with the board. Former board member Michael Boucher, a restaurateur and
property manager, is appealing a Cook County judge's decision to
dismiss his lawsuit over $500 in fines the board assessed him four
years ago over allegedly "obnoxious" behavior, according to a letter
sent to him from building management, accusing him of violating condo
rules. He has since sold his place, saying he has had a series of heart
attacks and didn't want stress over the building to trigger another.
Boucher (pronounced boo-SHAY) says he has spent more than $40,000 on
legal bills. He said in his deposition he was "humiliated" by the way
the board treated him.
"This isn't about money, it's about principle — I'm strictly a man of
principle," he told the Tribune in an interview. "It's freedom of
speech as far as I'm concerned."
The lawsuit led to depositions in which Boucher and others were
questioned over a variety of alleged infractions — including Boucher's
use of a four-letter word for excrement when describing a broken key
fob. The board alleged he yelled at an office worker and forced her to
accept $35 in cash — even though the office accepts only checks or
money orders — for a new one; Boucher said the entire incident was
In his deposition, Boucher said he told the worker "my key fob took a s---, which means it broke."
"You responded with, I took a s--- ?" a condo board attorney asked during his deposition, according to a transcript.
"No — it took a s---."
"It took a s---?"
"It — meaning it broke," Boucher said, later explaining that he didn't consider the term to be profanity.
He also denied describing a front desk worker as a "cocky bitch" to her
face after she refused to help him return a credit card bill from
another resident that ended up in his mailbox. He admitted saying it
but said he was across the lobby — not in her face.
"Is it possible that (she) heard you refer to her as a cocky bitch?" the condo board attorney asked during his deposition.
"There is a good possibility," he replied.
The deposition also included questioning about Boucher calling another
female worker a "f------ employee" and refusing to ride in the elevator
with her — another incident the board fined him for. Security camera
footage of the incident was played at the deposition.
As part of their response to Boucher's lawsuit, building management
said he had a history of being rude to staff, something Boucher denies.
In 2009, Boucher allegedly argued with a building employee about
portable electronic defibrillators. Boucher in his deposition said he
may have grabbed his chest and told the worker "these are my
defibrillators." But he denied lifting his shirt and exposing his upper
body, as alleged in a letter sent to him by the building management
company, accusing him of violating condo rules.
He also denied in the deposition allegations he had his pants' fly down
and exposed himself to a building employee and others at a board
meeting. Boucher was never fined for either of the alleged incidents.
The litigation has dredged up once-private emails between board members
that Boucher alleges show a campaign to target him with illegal fines,
including an email in which Milazzo writes: "I don't think I've ever
encountered such an unapologetically crude person in my life. It's
almost as if he's a cartoon character: The Mr. Magoo of slovenliness."
Milazzo testified at his deposition that Boucher's first words to him at a board meeting were a shouted "Hey, dago."
"I would consider that as a racist incident," Milazzo said.
In an interview at his spacious home in St. Charles, Milazzo — who
still owns the condo — said it was important for the board to take a
stand, even if financially it would be cheaper to forgive the $500 and
$1,000 fines. That's especially true when it comes to the legal battles
with Connolly, he said.
"Here I am volunteering my time, and the next thing I know I'm involved
in five lawsuits in five years because of this guy," Milazzo said.
He and Connolly agree that efforts to reach a truce have included a
push to have Connolly move out and turn over the blog's domain name.
"I said, 'Brian, if you hate this building so much, why don't you make
arrangements to move out?'" Milazzo said. "I know some people who would
pay to have him move out."
Connolly said he loves living in the building, with its prime location
and views, and that he isn't going anywhere. He said he's standing on
principle, too, and fighting for the rights of condo owners to get due
process instead of being fined by a politically motivated "kangaroo
"This is abuse of power," he said.
The fighting has been less contentious in recent months, and both sides
agree the board works better than it did four years ago. But Connolly
said the entire condo association model is broken, while Milazzo said
it works when people get along.
When there are disputes, Milazzo said the board has to be willing to
fight in court rather than be held hostage by litigious residents.
"Economically, yes, we could've just written off his fines and made
this litigation go away. but then he would micromanage every policy by
threatening litigation, not only against us but against future boards,"
he said. "So we said, 'We're going to take this all the way to the
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