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Mike Bailey, Jr.

Mike Anthony Bailey, Jr.

September 21, 1989 - November 6, 2019
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Obituary

"Look good, smell good, feel good,
Do your best and then do better"


Mike Anthony Bailey, Jr., 30 of Pittsfield passed away on November 6, 2019.

Born in Pittsfield on September 21, 1989, he was the son of Mike Bailey, Sr., and Donna Kent.

Mike was known and loved by so many, known for the sparkle in his eyes and that smile everyone loved.

Mike tried to live by his motto of "Do your best and then do better". Mike began his battle with addiction at the age of 17 after being prescribed pain medication for a broken jaw. Unfortunately, after a 13 year battle with addiction; addiction won. Addiction is a constant fight and daily struggle that many experience or suffer from but so few truly understand.

Mike had such a big heart and caring personality. He will be so missed and has left a hole that can never be filled. He graduated from Taconic and enjoyed dirt biking, fishing, hunting with his father and spending time with the love of his life, his little girl Maddison.

Mike is survived by his mother and her husband, Donna and Sean Kent of Pittsfield; his father and his wife, Mike Bailey, Sr. and Darlene of Pittsfield. Mike’s grandmother, Jean Sperling of Pittsfield; brother, Alex Kent of Pittsfield; a half-brother, Tim Rando; step-brother, Jose Ortiz of Pittsfield, and step-sisters, Angela Ortiz and Angelica Ortiz both of Pittsfield; and many nieces, nephews, aunts, uncles and cousins.

Most importantly, Mike leaves his pride and joy and his whole world, his daughter, Maddison Rose Bailey.

FUNERAL NOTICE: Services will be by invitation only as the family requests privacy during this difficult time. In lieu of flowers, memorial contributions may be made in his name to the Keenan House, in care of DERY FUNERAL HOME, 54 Bradford St, Pittsfield, MA 01201.
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Taylor Amstead

Posted at 02:40pm
Please accept my condolences. I am so sorry for your loss. I will always love Maddison and Siera. I think of them always.
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Breanna Brown

Posted at 07:26am
What we have once enjoyed we can never lose; All that we love becomes a part of us. Thank you for the beautiful memories Mike.
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Jennifer Kus

Posted at 09:19am
I want to give my condolences to the family for what they are going through right now. I just cant even imagine. But I would love to say how amazing your son was, we where friends on high school and he was always so caring, had a big heart and always made me feel welcome and comfortable no matter what. He was such an amazing friend.
MW

Mike Weliczka

Posted at 08:15am
Mike, Darlene and family,

We are very sorry to hear of Mike Jr.'s passing. Thinking of you during this very difficult time.

-Mike Weliczka and family

Brianna Sabato

Posted at 08:02pm
I am so sorry to read this. He was a great guy-I first met him in middle school and he was always polite and caring. We lost touch in high school but reconnected a friendship as adults. He was so proud of his girl.
From my memory I remember how proud he was, how he liked to try to start random football games and would always try to get anyone laughing. I never saw him judge anyone and truly tried to be friends with everyone.
You did raise a great guy, and I am so sorry this happened to you. I remember talking to him on trick or treat a few years ago when he was at a house on the Pittsfield/Lanesboro line(I think it was a friend’s house). He was handing out candy and we talked about parenting and how hard it can be and how you only wish for the world to be kind to your kids and he said that he’d be happy if he was half the parent his parents were. Again, I am sorry for your loss and Madison’s . He left his mark on people in a positive way and I hope that helps comfort you.
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