Sidney P. Tripp

sidney tripp

September 7, 1960 ~ December 21, 2020


Resided in: Portland, ME

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Portland- Sidney P. Tripp, 60, of Neal Street died unexpectedly at his home on Sunday, December 20, 2020. Sid was born in Portland, Maine on September 7, 1960 the son of Sidney P. Sr. and Mary A. (McGuire) Tripp. He graduated from Maranacook High School in the class of 1979 and then earned his Bachelor's Degree from the University of Maine at Orono in 1983. Sid spent his entire career working in advertising and marketing and in 1993 founded Proactive Resources. With his creative mind, strong work ethic and charismatic personality, he quickly established a very reputable and successful company which led to him becoming a driving force in the Portland business community. Sid will always be remembered for hosting 20 years of Portland's biggest Halloween bash. He was instrumental in the lineup of entertainment for Portland Pride for many years and in 2010 founded Downeast Pride Alliance, DEPA, a business networking group which met monthly on a social platform. Affectionally referred to as "The Mayor of Portland," Sid made friends everywhere he went. Portland will miss his larger than life personality and his wicked sense of humor. A life-long lover of antiques, Sid loved scouring flea markets for his next great find. He enjoyed nothing more than opening his home to his family and friends, welcoming everyone with a big hug, cocktails at the ready, 80's music in the background and a fabulous meal at a perfectly-set table. Sid was truly the ultimate host. He took much pride in his beautiful home and lovely garden, the envy of the West End. He enjoyed travel, especially summer trips to Nantucket and his many visits to Greece including one with Freddie and Paige to celebrate his 50th birthday. One of his last great adventures was taking his beloved niece, Rachael Mary-Grace, to Paris for her 30th birthday. Sid is survived by three sisters, Terry and her husband Stephen Comeau of NJ, Sandi and her husband, Dale Flagg of Augusta, and Rose Weymouth and her partner Lee Godin of Belgrade; his best friend of 32 years, Frederica "Freds" Jackson of Portland; nieces and nephew, Rachael Tripp and her fiance, Tyler Daigle of Scarborough, Sgt. 1st Class, Aaron Flagg of Germany, Hannah & her husband Ian Doe of Biddeford, Sydney Comeau of NJ, and Eva Flagg of Augusta. Sid's family would like to extend a special thank you to all of the amazing doctors, nurses and friends who cared for and supported him. Visiting hours celebrating Sid's life will be held on Saturday, January 2, 2021 from 2:00pm to 5:00pm at the Conroy-Tully Walker South Portland Chapel, 1024 Broadway, South Portland. Following state mandates, and for the safety of all in attendance, face masks are required. A celebration of Sid's life will be held at a later date. To view Sid's memorial page, or to share an online condolence, please visit www.ConroyTullyWalker.com Those who wish may make contributions in Sid's memory to: American Heart Association, 51 US-1 # M, Scarborough, ME 04074 or to the Animal Refuge League, 217 Landing Rd, Westbrook, ME 04092

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  1. Sid was truly one of the kindest people I’ve known. This I learned way back starting in Cony High School. He had a way of making you feel important and special which was no small task since he knew so many. His love of life was infectious and you couldn’t help but go along on this ride when in his presence. From his infamous Halloween parties at the Mariner’s Church, to his love of good food and friends, to antiquing at flea markets, he measured life by the company he kept and how he could share these experiences with others. His medical condition didn’t slow him down either and he proudly explained how his lvad allowed him to carry on. And carry on he did. A couple of years ago, I asked him if he would take me antiquing as I thought his skills were invaluable and I wanted to spend some time with him. He first wanted to make a pit stop to check on a piece of granite he’d had his eye on which would be the crowning glory for his new patio table. He felt dejected at first when he couldn’t find the piece, but he persevered, found it, paid for it and we went on our way. His mood that day was one of elation. He had so many plans of how his beautiful garden would be transformed by this piece of granite. He couldn’t wait to share this space with others. Later, we made our way to the flea markets in Arundel. We couldn’t walk more than 2 feet before someone called out his name. He helped me find a few pieces of milk glass for my collection and he picked out the cutest little red cast iron crab. I couldn’t figure out what he would do with it: card holder, toothpick stand, ring holder? I’m sure he found the “perfect” spot among his electic and beautiful collections. I didn’t see Sid often, but I always tried to text every few weeks just to check in. He recently reached out on Facebook to ask for suggestions for tv shows or movies to watch. He was bombarded with hundreds of answers . Just a few weeks ago, I texted him with another suggestion-Grand Designs. He said,”That sounds right up my alley. I’ll take a gander!” He was always positive and upbeat even through these crazy, trying times. But that’s who he was and I will endeavor to have some of that rub off on me. Sid was kind, fun loving, warm and inspiring and I will miss him dearly

    – Lorene Rothstein DeWolfe

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  3. Sid was our neighbor for 30 years or more. He was totally committed to the ‘hood and was proud of improving his house and especially developing his incredible garden. We participated in the yard sales he organized with neighbors and always ended up buying some of the stuff that he had accumulated for his unique offerings… We loved our intersections with him. His insights and opinions were always expressed freely and with emphasis! He was a wonderful neighbor, always looking out for us and to chat. While we were well aware of his medical challenges, we were nevertheless shocked by his unexpected passing, especially during the holiday season he so loved. We will always remember and miss him.

    – Harry and Anne Pringle

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  6. I met Sid as my next door neighbor at The Old Port Arms on Exchange Street in the 1980s. He was energetic, very funny, friendly and very fashionable. He was always willing to stop and chat when we would cross paths in the hallway. Fast forward to 1996. I applied for a job in advertising in the Old Port at Proactive Resources. Who was the owner? Sid Tripp. He hired me and I eventually was promoted to Sales Manager. I worked with a great guy named Deane Porter and we both had so much fun working under Sid’s tutelage. Lots of lunches in the Old Port and we helped with Sid’s legendary Halloween Bash in the Old Port. After 2.5 years I moved on to another job but I kept in touch with Sid on Facebook. I always enjoyed reading about his epic experiences in many Old Port bars with his bestie Frederica Jackson (Freddie or Freds). They were inseparable. Sid had an amazing home in the West End filled with all the antiques and treasures he would buy and display. I attended many parties in his home and met the best people there. Sid had issues with his ticker and eventually received an LVAD device to help pump blood to his failing heart. He handled it like a boss but it definitely was a challenge to Sid. https://www.sunjournal.com/…/pump-and-a-bag-keeps…/ This month his poor heart had decided it was done and it took my friend with it. Sid leaves behind many dear friends, family and business associates. He was the textbook definition of ONE IN A MILLION. My experiences with Sid made me more focused on diversity as Sid was an openly gay man. When I worked at TD Bank I volunteered to be part of its legendary Diversity Committee at the Auburn Contact Center and I even wrote the committee’s mission statement in honor of Sid and his willingness to befriend me and my heterosexuality, allowing me into his special and magical world. I carry on his openness every day.. Sid, you will be remembered and missed until my last breath. Rest in Peace buddy..

    – Dan Blake

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  7. So sorry for the family to lose such a beloved brother and friend. My love goes to you all . Sid loved his family and Frederica very much. They were his first priority. Sid invited me to tag along on family cabbage island clam bakes as an adoptive Auntie). He was very kind, thoughtful, and very intelligent. Rose and I enjoyed giving him antique Christmas ornaments which he cherished. You made a difference in many lives Sid. God bless Sharon wheeler (Auntie) as the family knows me.

    – Sharon Wheeler

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  10. It has been years since I’ve seen you, but I can hear your laugh still. You were always full of smiles and often a naughty joke. You made me blush countless times. You were larger than life and will live on through the many, many friendships you made through the years. May all who are grieving find peace in the memories of you. ‘Til we see each other again, Sid, xoxoxo

    – Janice

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