Caroline Douglas


You follow a case as it winds its way through the court system.  It seems so simple, so cut and dried that you wonder why so much time, money and hostility is invested in such a petty argument.  Why should it cost hundreds of thousands of hard earned dollars to figure out whether a homeowner in an association can have white roses instead of red ones?  Or whether or not a condo owner is allowed to have a small American flag on his or her front porch or if a family can have a swing set in the backyard for their children?  Why should these even be an issue?  And why would anyone in their right mind care?  And finally, after months of discovery, nasty letters, fines, bullying, isolation and abusive language, dividing up the neighborhood, name calling and other nastiness, the opinion from the judges is handed down deciding the case once and for all.  This is it, this is the end of this road. The wise men and women of the legal system have spoken and you are left with your mouth hanging open, wondering what on earth just happened.  

Caroline Douglas joins us On The Commons.  Caroline has a law degree although she is no longer a practicing attorney.  She has seen the dark side of the legal profession and decided to blow the whistle on what happens “behind the scenes”.  In an 800 page book called “The Dark Side: a law treatise on judging – with memoir” she explains it all and gives us clues to look for so we are not caught off guard.  In a fascinating interview she walks us through what goes on behind the scenes and how and why some of these off the wall decisions are reached.  Caroline has witnessed these irregularities both as a practicing attorney and a litigant caught in this legal “chamber of horrors”. You can reach Caroline at but you won’t want to miss this interview. 



2 thoughts on “Caroline Douglas”

  1. Very interesting interview!

    I’m most familiar with the legal system due to HOA issues that I’m a part of and those I have sat in the courtrooms and observed. As I see it, the biggest problem is the attorneys do not understand how the HOA system works. They do not understand how corrupt and evil those in higher positions within the HOA and the CAI truly are. And they do not understand how one homeowner struggles to fight their HOA and the insurance company that represents the HOA against the homeowner/condo owner. The homeowner makes a purchase into a situation where they can do nothing except come out a loser. That often costs them their health, happiness, bank accounts, and retirement savings. They can end up penniless and homeless even if the HOA is 100% in the wrong.

    From this interview I’ve learned the law schools are teaching the attorneys how to turn every case into a cash cow. (Unless I read something into what I was hearing that isn’t true.)

    The lack of education about HOAs and the legal industry are definitely destroying home ownership in America! The homeowners cannot win! If the judge is also in on the take there is no hope at all for those homeowners who are being victimized. It’s disgusting and maddening!

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