The Most Jaw-Dropping Family Secrets Finally Unveiled

37. Catherine and James

My mom has twin cousins, one of whom “ran away” with her boyfriend in the 90s. Her name was Catherine.

She ran away with a man, “James” she met through my grandfather. James and my grandpa used to place illegal bets together in the back of a sub shop in Southie (South Boston). My grandma thought he was such a good catch; he loved kids and animals, and was well… respected in the neighborhood. She never let anyone speak ill of him because she said that he “kept the neighborhood safe for us Irish immigrants.”

Catherine and James went missing together in the summer of 1991.

I found out as a teen that James really went by “Whitey,” as in Whitey Bulger, the infamous Boston Irish mafia boss. Convicted of 18 murders, suspected of 3 dozen. Convictions for narcotics, extortion, and racketeering. In the 50s, he spent 9 years of a 20-year sentence at Alcatraz for bank robbery. The same dude who came to dinner with my grandma and older relatives in their backyard on nice summer days.

He was captured in 2011, after 16 years on the run. He was killed in a Virginia prison in 2018. Catherine served 9 years and is said to now live with Bulger’s relatives, or her twin sister, in Massachusetts.

The films “The Departed” and “Black Mass” are both based on his life.

Illustrious-Science3

38. The World Makes Less Sense

My dad identifies as a woman and has decided to begin the transition.

In a way, this has made a lot of things make less sense, but it explained all of these little things I had overlooked about my dad – him shaving his legs “because he felt like trying something new, and wanted to see what it was like,” always attending LGBT events (I just thought he was super woke), and every Thursday when he would go to knitting club and come back with feminine items (my brother thought he was cheating). I always thought it was cool that my dad challenged the gender norm by being a male knitter, so I was mildly disappointed by the news.

They kept it a secret for so long because my brother and I went to Catholic school from k-12, and they were worried about what would happen if other parents and kids found out.

39. Bad Examples

My Dad never really let us interact with my Mom’s side of the family. We were always told it was because they weren’t very righteous (I was raised VERY religious) and would be bad examples to us kids. Found out this year that it was really because my Dad at one point was dating my Mom, and two of her sisters at the same time. He then married my Mom, and then stole a car from her father, beat the sh*t out of her siblings when their parents weren’t around, and skipped town without warning one day and never told them where they went…

Her side of the family is dope, and I am hanging out with them today.

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40. Putting Forth Some Good Feeds

My dad ran a free clinic in India for two years after he completed medical school. He didn’t want anyone to know about it because “give with the right hand so the left-hand doesn’t know.” We found out after he died, when we went to India one of his patient’s children told us how he helped their mom with a serious illness she couldn’t afford to treat.

41. It’s Bad for the Mistress

Grandpa had a whole house with a whole family living in it that no one knew about. It is only because he has Alzheimer’s and grandma is the one who is in charge of everything that we found out about the property and the family living in it. It is grandma’s property now since grandpa can’t do anything anymore and she is pondering what to do about it. She doesn’t want to be mean but she paid for over half of that house and she wants her own kids to live in it. Sucks for the mistress.

Abeyita

42. Gambled it All Away

My grandpa absolutely adored his grandkids (just me and my brothers). He sold all of his belongings and moved from Missouri to Virginia (where we live) and lived a modest life in a trailer just so his entire income could go to our college funds.

He died when I was 10 and my grandma died less than a year later. When me and my brothers went to college I noticed my parents were having trouble paying for our college. This shouldn’t have been the case because I knew my grandpa had A LOT of money. I had just assumed it was because my college’s tuition was particularly expensive.

My mom’s mom let it slip one day when me and my brothers were 20 that when grandpa died he didn’t have a will. So all the money went to my grandma. But grandma was so devastated by her husband’s death that she never went out and got her own will. She died suddenly before she ever got one. But doesn’t that mean her only son, my dad, gets all of her belongings? Nope. Turns out my dad wasn’t her biological son. My dad’s bio mom died while he was in college long before I was born. There was no reason all this was kept from me and my brothers, it just was. The money ended up going to my grandma’s only living brother: a gambling addict I knew nothing about. My parents pleaded with him; he can have everything else, just give the kids their college funds. That’s the /only/ thing grandpa asked for on his deathbed. But no. He refused and gambled it all away.

My brothers and my parents are all in debt now, which is the last thing grandpa wanted. But what keeps me from being angry is that I know just how proud of me he would be just for graduating college at all.

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43. She Sent Me Away

I found out 2 years ago that my mother had a baby she gave up for adoption 18 months before she had me and then had another baby when I was 3 and she also gave that baby up for adoption. All 3 of us have different fathers and I think the only reason she kept me was that my father married her but that marriage only lasted a year. My mother remarried when I was 5 and my (half) brother was born when I was 7. As far as I knew for 59 years he and I were our mother’s only children.

I never saw her pregnant with the 2nd baby because she sent me to live with my great-grandparents across the country during her pregnancy. My mother and grandmother were the only people who knew about this and they both took the secret to their graves.

The only reason any of it was found out is because of all of the DNA testing people now do. This discovery really impacted my sense of identity for a while, my view of my mother, and our relationship.

I’ve met my half-siblings, an older sister and a younger brother. I like them and I’m glad I’ve been able to answer some of their questions but the initial discovery really messed with me for a bit.

44. The Best Step Dad

My stepdad had a secret daughter and was almost charged with attempted murder because of it.

When he was in his late 20s, he started dating a woman in his apartment complex. After a few months, she cut off all contact. Turns out, she got pregnant, but was super married and never told him.

Her husband must have been a special kind of unaware, because she hid the pregnancy from him, covering it up by claiming she had stomach cancer.

When she delivered, she left the baby in a dumpster. It was found and rescued by a janitor at the hospital.

The woman came forward a few days later. My stepdad knew nothing about the pregnancy at all and hadn’t heard from her for the better part of a year.

As soon as he saw the baby, it was undeniable it was his, and he did everything he could to claim custody while having to go through a rigorous process to prove his innocence.

He also had to go through months of parenting classes, and prove that he deserved to keep the child.

In the meantime, the story made national headlines and offers for adoption were pouring in. But he is absolutely a “family is family” person, and was determined to get custody of his child from the state (the mother was now very much in jail).

After a long process, he finally had custody of his daughter. However, he was in his late 20s, working a demanding on call job, and his first wife had just abandoned their toddler son at the demands of her new husband.

He was living in a sh*tty apartment, working 65 hours a week, usually overnights, and now alone taking care of two children under the age of 3.

Within a year or so, he finally caved and gave his daughter up for adoption. The family was very wealthy, lived in a great area, and were unable to have a child of their own.

He even tried to negotiate being a part of her life, but the family felt it would be best to raise her as their own. It killed him, but he agreed and agreed not to contact her, under the stipulation that she be told what happened when she was of age.

Within a few weeks of her 18th birthday, she located my stepdad. He and my mom were well-married at this point (my mom knew about this from the beginning).

He and my mom had moved out of state when I was 20, and it took a couple of years before I was ever able to go visit.

So as my mom was in town, and we were planning my first visit down to them, she told me basically “by the way, this is a thing that happened, and when you’re visiting, your stepsister will be down here as well.”

She and her adoptive mother (her adoptive father passed away shortly before her 18th birthday) are now very much part of the family.

His son had a pretty rough life and unfortunately died of a heroin OD on his 25th birthday, just a few months after meeting her.

I went back and read all the articles I could find about it. The quotes in the articles are so purely him.

Also purely he is the fact that he’s spent the last 25 years STILL turning down offers to be on shows like Oprah, Ellen, etc, and numerous paid book deals, and the like. All he ever wanted out of the whole situation was to provide the best life he could for his daughter, even though that meant giving her up.

She now does a lot of work with Safe Haven. She’s kind of a typical mid-20s girl. You can tell she kind of loves the attention she’s gotten from it, and I believe she’s actually accepted a book deal – much to his chagrin – but at the end of the day, the work she’s doing IS a net positive, so he’s happy to support her endeavors.

He’s one of the most loyal, honorable people you could ever meet. It’s never unclear to him what the right thing to do is. Life has thrown him a lot of b*llsh*t for his efforts, and even though I always generally liked him, it’s uneasy to really see a stepdad as part of your parental unit, especially when they come into your life when you’re already nearly an adult, but reading and learning about how he handled that situation earned a lot of respect and adoration from me, as it made me realize that all the kind things he did for me growing up had nothing to do with the uneasiness of being a step parent, or anything to do with making my mom happy – he was doing them because, without hesitation, he knows the right thing to do, does it, and his greatest pleasure in life is to help people and make other people happy.

My real dad is no slouch by any means, and very much part of me, but even though my stepdad has never once felt the need to teach it or explain it to me, I learned the joy of selflessness, and the value of true morals – not the kind you have to do mental gymnastics to justify – from watching him.

God, what a good guy he is. I should call him tomorrow.

45. He Looks Exactly Like Him

One week before my younger sister’s wedding, my dad decided to call me, both my sisters, and my mother (his ex-wife) to meet at his house for something “very important he needed to tell us.” We all thought he had cancer or something. We were very worried. Once we were all there, he sobbingly confessed to having a 5-year-old son living in the town next to ours, which means the kid was conceived and born while my parents were still married. He claimed he didn’t know for sure that the kid was his, and he had only recently gotten a DNA test. He showed us a picture of our half-brother. He looks EXACTLY like my dad. My mother was devastated.