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Passing: Diane Louise Winchester

Diane Louise Winchester died Saturday, Aug. 12 surrounded by the warmth of her family. Despite extensive health struggles and an exhaustive quest pursuing medical treatment options, she lived a beautiful life. She was 71 years old.

A lifelong Alaskan and vibrant member of the Anchorage community, her passion for life was boundless. A brilliant businesswoman, Diane’s flagship, Aurora Fine Art gallery, is in the heart of downtown, along with her shops Zoez Window Gallery and Alaska Max Gourmet. However, she found the greatest joys in life with her family.

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Diane is survived by the love of her life and best friend, Jerry Winchester, and their four children and their partners: Chad Renner, Brandon (Andrea) Renner, Jeff (Nicole) Winchester, Tonia (Brandon Milton) Winchester; and eleven grandchildren — Zoe McHenry, Max Renner, Madeline Renner, Emma Renner, Aliann Winchester, Kyrra Winchester, Quinn Winchester, Ian Milton, Chance Milton, Sawyer Winchester Milton, and Ivy Winchester Milton.

Born June 25, 1952 at the old Providence Hospital in Anchorage to parents Howard, a bush pilot/businessman, and Nina (Stone) Fowler, an executive director of a local bank, her first childhood home was a log cabin on the 700 block of O street. Coincidently, that log cabin was only a couple blocks from the loving home she created with Jerry over the last 30 years. It was her mother’s influence and unwavering confidence in Diane’s abilities, along with a $200 gift, that Diane attributed as the launching point for her academic, artistic, and business successes. 

Diane’s artistic talents, especially as a singer, emerged early in life. She was always the lead and truly a standout performer. After graduation from Dimond High School in 1970, she started a family with the birth of sons Chad and Brandon. Her special energy, talents, and strength were always evident. In her early years of motherhood, she balanced the profession of accountant for the family business, a wide range of singing engagements (including a steady gig with a Rock ’n Roll band), and the pursuit of higher education in music at UAA.

Diane’s angelic-yet-versatile voice landed her in Monterey, California during the 1980’s. She was a bonafide professional singer with agents for nearly a decade. Always family first, Diane continued to change with the needs of her sons, leading to a position as Seagram’s lead cost account and a path back to Alaska.

Most remarkable and memorable was her magnificently and consummate style, grace, and elegance. It poured into every aspect of her life. It created a richness as she deliberately immersed her senses into each moment to connect with the world, art, artist, the community, and most importantly, as a loving mother, grandmother, and wife. Diane’s legacy is her unparalleled love and connectedness to share the beauty of life.

With her entrepreneurial spirit and meticulous style, Diane quickly advanced in the world of gallery art. Within a year, her quaint 400-square-foot shop to exhibit Alaskan artists evolved to the present-day Aurora Gallery. Nearly simultaneously, Diane’s love story with Jerry truly began.

It was a time of new beginnings. With a shared faith and trust in God, Diane’s life with Jerry blossomed with beautiful blessings and soared to the heavens above.

As life partners and dynamic teammates, they complemented each other and business thrived.

The mayor appointed Diane to serve eight years on the Anchorage Museum Board of Directors. She was an Honorary Commander on Joint Base Elmendorf-Richardson three times, continuously engaged in philanthropic pursuits, and was an active member of the Rotary.

As president of the Anchorage East Rotary Club, the organization spearheaded an effort to improve quality of life issues in Nepal through a local charity called Helping Hand for Nepal. The couple witnessed the impacts of the charity first-hand during a mission trip to Nepal, which touched their hearts and made a lasting impact.

Their 30-year journey together was full of joy, excitement, and adventure. Diane was a world traveler, skilled skier, marathon runner, outdoor enthusiast, and took to the skies as a helicopter pilot. She lived life to the fullest.

Whether holding hands with Jerry on the streets of Barcelona or connecting in the quiet of Trapper Lake, Diane’s favorite place was at Jerry’s side. Together as kindred spirits they lived a life of incredible passion and oneness.  

The family wrote, “Though we rejoice that Diane is at peace with Jesus, we will greatly miss her presence here on earth. We will treasure her legacy and Praise God for her life well lived.”

In lieu of flowers, please consider a donation to Helping Hand for Nepal. .

Diane’s celebration of life will be held at the Anchorage Museum on Wednesday, Sept. 6, 2023, at 6 pm. A reception with light refreshments to follow.



  1. There it is “It was a time of new beginnings. With a shared faith and trust in God.” I held my breath what a relief to answer my child’s question was she a Christian with yes she was a Christian- we both relieved- since Aurora Gallery is one of her favorite places. She appreciated its higher quality art, the store’s elegance, its rich culture and heritage, and non assuming warm hospitable environment with its intelligent gallery workers who could tell the difference between a cultured well mannered 3-four year old up to 7 yrs when we were most active visiting -and a wild one to not embarrass her, staff treated her smartly which made the place live up to its qualities to a little child whom appreciates the meticulous detail that makes art Fine Art.

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