Their mum was killed by their father when they were just toddlers.
Then, in 2003, Marcus and Hamiora Taylor Day's brother, Ryan, was killed in a car crash.
In 2015, their sister, Horowai, was struck by an aggressive gastric cancer which saw her die before their eyes just months later.
Now the brothers, aged 23 and 25 respectively, are also battling cancer after being diagnosed just months apart.
Family have since set up a Givealittle page to help the surviving brothers with their ongoing costs of getting treatment at Waikato Hospital.
Marcus Taylor Day told the Herald suffering so much tragedy, which also included the death of his grandfather and break-up with a former partner, he'd nearly talked himself into joining Isis before attempting to take his own life on the rural Te Awamutu property where he was living at the time.
But it was after that moment, during which he'd said a prayer, that he realised he wanted to fight for his life and not let his cancer get him down.
Taylor Day said his mother was 25 years old when she was beaten to death by their dad in New Plymouth in 2000.
Day, dubbed a "cruel, violent and vicious person" by the sentencing judge, had beaten her on numerous occasions prior to her death, and even served two prison terms.
Taylor Day, who has always been vehemently against family violence, said even though he was only young, about two years old, he still recalls the beatings being handed down to his mother.
"I still have flashbacks of it when I sleep ... I remember certain things. I remember sitting on the stairs and listening to it and my sister grabbing me and my brothers and the old man was laying into my mum."
In 2003, their youngest brother, Ryan, who was a month shy of turning six years old, died along with his aunty, Pauline Rehia who was pregnant with twins, after the vehicle being driven by their uncle, Robin, crashed near Porirua while travelling to their grandfather's tangi.
And in January 2015, his sister started suffering debilitating stomach pains. She was hospitalised and a month later diagnosed with stage 3 gastric cancer.
She died three months later.
Taylor Day, who recently moved to Auckland from Te Awamutu, said watching his sister, who he described as his "best mate", die so quickly had been one of the toughest things he'd experienced.
He also was battling with his biggest regret - that he had not sought help sooner.
Now a father of three kids, aged 4, 18 months and 11 weeks, he put up with severe stomach pains for the past two years, before finally getting help.
The pain got so bad that he couldn't swallow his own spit.
He was diagnosed with stomach cancer in early June, with a stage 1 carcinoma. His stomach will eventually be removed.
For the past five weeks, older brother Hamiora, 25, has been in isolation in Waikato Hospital battling stage 3 lymphoma cancer, which has formed a large, aggressive, tumour in the side of his torso.
Now that he's accepted his diagnosis, he was determined to try help others, especially young men who were too staunch to see a doctor.
"I was shrugging it off as my alcoholism, my prognosis was 'oh, I've just been drinking too much' but in the back of my mind all the time, I was thinking, 'nah, something's wrong with me' it was just my pride got in my way."
He said men needed to stop trying to be "tough" and go and see a doctor if they felt unwell.
"I really hope that by doing this story I can reach out to one or two, three guys who don't care, and help them get over that pride and find true mana and take pride in their health. If you're feeling a bit sick, go see your doctor. It can save your life."
Taylor Day said he was confident he will fight his cancer.
"I'm gonna be alright, I'm going to make a full recovery. The way I look at it I haven't caught cancer, cancer has caught me and I'm here to kill it ... I'm not going to let it beat me."
• To donate, head to: givealittle.co.nz/cause/young-brothers-battling-cancer
Where to get help:
• Lifeline: 0800 543 354 (available 24/7)
• Suicide Crisis Helpline: 0508 828 865 (0508 TAUTOKO) (available 24/7)
• Youthline: 0800 376 633
• Need to talk? Free call or text 1737 (available 24/7)
• Kidsline: 0800 543 754 (available 24/7)
• Whatsup: 0800 942 8787 (1pm to 11pm)
• Depression helpline: 0800 111 757 (available 24/7)
• Rainbow Youth: (09) 376 4155
• Samaritans 0800 726 666
• Rural Support Trust: 0800 787 254.