Wilbur Albert Daly (Bailey) was born on November 21st, 1972, to Esmie Weekes and Aiden Albert Fredrick in Plymouth Montserrat. Wilbur was their first child together, shortly after Esmie met Uncle Rupert and later welcomed Wailon, Warrick and Warren. Following Fredrick falling in love with Aunty Joycee welcoming Carl and Jissele, all of his siblings who he loved dearly.

As a child Bailey was curious; he loved walking through his village fetching buckets of water to bring back to his mother, walking the cows and goats accompanied by Wailon. He would run around with his friends getting into idle trouble, raising havoc and laughter amongst the community. Throughout his life he had many passions one being music another being cutting hair which soon became his long-term career.

In 1984 He migrated to Brooklyn, New York where he lived with his dad and his Stepmother Aunty Joycee, where he attended George Wingate High School Leading him to become the best of friends with Nike, Franky, Joel, and Norris. During this time, Bailey developed a fascination with airplanes and a deep desire to learn how to fly. His passion grew so strong that he began taking flying lessons, pursuing his dreams of becoming a pilot.

In 1993 he moved to Boston to start a life of his own, shortly after he welcomed his First and only son Baili-Jakeem Daly. Soon after, in 1997 at the age of 25 Bailey opened up his Infamous barber shop Classic Cuts in Hyde Park Massachusetts, Bailey made a tremendous impact in the city from cutting hair, it wasn't just his career it was his lifestyle. He was so deeply devoted to his career that he developed long term strong connections with his clients; they became more than friends; they were now seen as family.

Shortly after he met his soulmate/lifelong partner Trish. Furthermore, becoming one big blended family including his stepchildren Ronnie and Bryana. Soon after they welcomed their beloved daughter Dyman Vondina Daly in 2000, while also becoming a bonus grandfather to Trish's granddaughter Sah’ranei. Bailey and Trish established the rest of their life in Milton Massachusetts. Where they raised their children in a two-parent loving home. Within that time, he also created irreplaceable friendships including Dwayne, AL, Wayne, His cousin better Known as Pastor Wayne Daly and among many others. Nevertheless, throughout the years Bailey continued to be a loving father and a hardworking businessman. In 2019, Bailey began working for UPS as a delivery driver, where he quickly became a beloved familiar face to many. Throughout his time there, he formed meaningful relationships with his coworkers and countless families in the neighborhoods he served. His warm personality and genuine kindness left a lasting impression on everyone he encountered. Bailey became so well-known and loved throughout his delivery routes that even local high school students would honk their horns in excitement whenever they saw him driving by.

Bailey's legacy continued to grow when Dyman welcomed his first grandson Damias in 2021. Following his second grandson Dymani in 2022. He loved his grandsons as if they were his own. His love was so unconditional he referred to them as the apples of his eyes. The life Bailey worked extremely hard for finally felt complete once he had his grandchildren.

As Bailey grew to learn himself, he began to start taking his health a bit more seriously, from going to the gym twice a day, to doing natural remedies before a doctor or hospital even came into consideration. He took pride in knowing if he looked good, he felt good. Bailey enjoyed the simple things, from spending time with his family, taking long rides on his Red and Black triumph motorcycle (back when it was bike life), to going on hikes, late summer nights in the cape on the beach, from rides in his drop top jaguars, to blasting his favorite music and then settling it down to political podcasts.

Wilbur (Bailey) Albert Daly will be deeply missed, but his memory will live on forever in the hearts of all who knew and loved him. His love, laughter, his long talks, his stubbornness & wisdom. To know him was truly to love him. The memories he created with his family and friends will continue to live on through each of us. Though we have to fiscally say goodbye, his spirit and the love he gave us will never leave us. May he rest peacefully, knowing how deeply he was loved and cherished and how greatly he will be missed. Until we meet again.

Visitation will be held at Faith Christian Church, 301 Harvard Street, DORCHESTER on Thursday, September 17th from 9-11AM. Funeral Service to begin at 11AM. Relatives and friends invited. Interment is private.