It is with great sadness we announce the passing of one of our long-standing family members, Rupert Davis, affectionately known as Rupie.

Rupert would have celebrated his 39th year at Jamaica Inn this March. He was one of our bartenders and also our croquet master who frequently taught guests how to play the game. Rupert will be fondly remembered for his warm smile and dedication to his craft.

Please share your memories of Rupie with commentary below.

He will be dearly missed and we extend our deepest condolences to his family and friends.

With love,

Your Jamaica Inn family

102 comments on “Fondly Remembering Rupert Davis

  • Alasdair Mackay says:

    My heart goes out to everyone of his family and work mates, My self and my wife met Rupert last year and he was a super warm and welcoming person, he encouraged me in to playing croquet with him and a few other guest. He will be so missed. He was a true croquet master.

  • Crystal and Ray says:

    Best marriage advice ever for newly weds…”Go home early and don’t come out” LOL! We will truly miss our long conversations about life and family over our freshly made fruit punch and planters punch!

  • MAXINE WALTERS says:

    OMG! Uncle Rupie!!
    He was a gentle giant with a warm smile and a big hug for me always.
    To be at Jamaica Inn and not see Rupert will be a great sadness. His warmth, tireless patience while teaching croquet and genuine love of Jamaica Inn and all who passed through its doors was genuine. I shall miss him. My condolences to his family. May he rest in peace.

  • Bobbie & Gudmund Iversen says:

    Rupert was a gentleman, a dedicated part of the Jamaica Inn family, a thoughtful individual, and a delight to be with! He was generous with his time, his service, his bear hugs, and his always-welcome smile. For us, over the past 15-20 years, he epitomized so much of what we love about Jamaica Inn. Please give our fondest and most respectful condolences to his family. We will keep Rupert in our hearts always.

  • Jack Rehner & Chris Lannon says:

    We are absolutely heartbroken at this news. Rupie was one of the shining stars of the Jamaica Inn and a dear, dear friend. Over the years he became like a family member and we always were eager to see him upon each visit. His croquet skills are legendary, but he was also a fabulous ambassador for the Inn with his smile, twinkle in his eyes, and constant desire to take care of his guests. It is inconceivable to imagine a visit to the Jamaica Inn without Rupert. As wonderful as the Inn is, there will forever be something missing without Rupert. Our sincere condolences to Rupert’s family as well as his Jamaica Inn family. Rest in peace dear friend.

  • Steven and Shelly Cornett says:

    Although we loved all the staff members at Jamaica Inn Rupert was one of the most memorable. He was so kind to my wife and I during our week celebrating our honeymoon. Each afternoon we played croquet and he showed great patience with us while teaching us the rules of the game he so dearly loved. After the first day playing croquet he refereed to my wife as “partner” the rest of the week and she loved it. If we passed by him at breakfast you would hear him say “Hey Partner” in his Jamaican accent and it always brought a smile to our faces. We still talk about him to this day. His kind spirit and his infection smile is something that we will always cherish.

  • Rosemary Attenborough says:

    Such is the speed of communication that many of the February Crowd are already mourning the departure of an old friend and have sent condolences. Have known Rupert for about 20 years and watched as his tummy got bigger and his mastery of croquet became unsurpassed! I trust the Almighty has a lawn waiting for him and the Angels are ready for a Masterclass from a lovely friend who will be much missed but not forgotten. Rosemary A.

  • Sad to hear about Rupie – not six months ago he was whupping youngsters down from Kingston every weekend at croquet. The saints in heaven have no chance. A big part of the tradition of Jamaica Inn.

    RIP

  • Dear Rupie you will be very much missed. I loved our conversations on the beach, and your
    Sweet smile. Rest in peace, I’m sure that you are surrounded by the angels.
    My deepest condolences to all the Jamaican Inn family
    Noemi Marone Cinzano

  • Steve Nicholson and family says:

    Rupie will be sadly missed by us and I fondly remember the many times that he would crack open a coconut and fill a bottle for me to take back to our room. Thank you Rupie.

  • MG and Mrs Donald R. Lasher says:

    I just learned hat Rupert Davis has died. How very, very sad! Rupert was an “institution” at The Inn.
    He will be sorely missed by all of us “regulars”. He was also a very nice and caring man.
    For us, it will never be the same without him. Too bad.
    May he rest in peace.

    Don and Nadia Lasher

  • donna and darren mcbain says:

    Sad news, we loved Rupie so much….We will always remember his famous words “Hit the Red Ball”!!!
    Donna and Darren McBain

  • Peter & Carole McCarthy says:

    Rupert was a warm and gentle giant. He always had time and a smile and a kind word for everyone. He will be missed by all who knew him.

  • Plinio Franzini says:

    We are sorry, his death is a great loss. We want to express our sadness to the staff of the Jamaica Inn and to Rupert’s family.
    The Franzini family

  • Dottie and I are deeply saddened to hear about Rupie’s passing. We have always felt him a part of our family and will truly miss his presence when we arrive in April. He has been such an exemplary fixture, pleasing personality and shining example at the Inn. Always smiling, happy, warm and wanting to make our stay special. We extend to his family our most sincere condolences and will offer prayers in his name.

  • Peter Rosengard says:

    This is terribly sad news! In fact I can’t quite believe it as I read it here in London : I only said goodbye to Rupert ten days ago after my annual two weeks stay at the Inn. For me Rupert IS Jamaica Inn. The warmest ‘welcome back’ always came from Rupert. Every morning over the last ten years or so of my stays he’d stop by my verandah on the beach wing for often the only conversation I would have all day- and we’d ‘ chew the fat’ after I’d read the Gleaner.Rupert was simply ‘the best.’.. a true legend always gentle and kind..and what a presence he had! I shall miss him enormously: Please give my sincere condolences to his family. -Peter Rosengard.ps Rupe’s patience every year whilst trying to teach me how to play croquet was truly remarkable -as I am definitely the worst player in the history of the game.

  • We are really sad to receive this news. Rupie was one of the people we most looked forward to seeing when we returned for our second visit to the Jamaica Inn. He was so friendly and great to talk to, had plenty of funny stories. He always made us feel comfortable and was a great crochet instructor. We will miss seeing him there next time we visit

  • Gillian and Gary Bullock says:

    So sad to hear about Rupert’s death. We have just been discussing returning to Jamaica Inn this year…we will miss him. Our heartfelt sympathies to his family

  • Rupie was one of a kind. A true gentleman with a very caring and attentive way about him. He remembered me on my second visit to the Jamaica Inn and I am so sad to hear of his passing. Many condolences to his family and friends and to all of you at the Inn who will miss him so much.

  • So sorry to hear of you loss. RIP Rupert. You were an absolute legend and it was such a pleasure meeting you.

    Thoughts are with your family and friends.

    Much love, Teri

  • Rudy and Catherine Giuliani says:

    We are heartbroken!!! Rupert was like part of our family. He will always be part of the Jamaica Inn’s soul. We have so many fond memories of Rupert and we will never forget him. Please extend our condolences to the entire staff and especially to his family. We are blessed to have known him.
    May his memory be eternal.
    Sincerely,
    Cathy, Rudy , Rudy Jr. and Alexandra Giuliani

  • Carolann Clynes says:

    Rupert was a true gentleman with few words and a big heart. My husband and I have known him for over 25 years, so he will be sorely missed. Lunchtime at the beach bar with Rupert and lessons at the croquet court will never be the same for us.

  • Bryan Zawikowski says:

    Rupert will be terribly missed. He was an old friend and fierce competitor on the croquet lawn. After 15 years I think I only bested him mano-a-mano once…not including wins “at the post”…those are “ties” according to Rupie, His sense of humor will be missed as well. When his doctor asked him why his belly was so big, he said: “..well, doctor…you told me to watch my weight, so I put it in front, so i could see…”
    Goodbye Rupert…enjoy the great croquet lawn in the sky. We’ll shoot it out when I get up there with you

  • Leigh and Tim Walsh says:

    So very sad. We were always so excited to see him and play croquet with him each time we visited. Our prayers are with his family.

  • We are so sorry to hear this. He was amazing man, always had a smile on his face and what a voice!!
    He will be missed…R.I.P

  • Steve and Andrea Cross says:

    We are so sad to hear about Rupert, he was a true gentleman and to us
    represented the very best of all that makes Jamaica Inn such a special place.
    He always looked after us so well and was so thoughtful, he was a friend who
    made our holidays special
    We shall miss him but never forget him

    made our holiday

  • Steve Landsberg says:

    Sad news, indeed. My deepest sympathy to his family at home and at Jamaica Inn.
    Every morning when we saw Rupert walking towards us on the beach with his tray of glasses of rum punch, we knew it was going to be another wonderful day. Rest in peace, sir. And cheers.

  • Dear Jamaica Inn and Friends,
    We had the pleasure to spend a week with Rupert. Every morning when we would see him, a smile came to our faces. Don’t let that cute shy demeanor fool you, he was a shark at croquet! I was an easy mark to be taken for a few Gentlemen bets.
    We have found memories of our stay and the interaction with the staff. Rupert was surely the highlight of my days. Someday, on that island in the sky, I expect a few rematches. God Bless
    John and Francine Bufanio
    Marlton, NJ

  • Rupert was a fine man and gentle man. He was key to our enjoyment of the Jamaica Inn. His company and advice were always appreciated My sympathy goes out to his family for their loss.

  • Bud & Waverly Henderson says:

    I was deeply saddened to get the email on Rupert’s passing, and it is with a very heavy heart that I type this message. Please, know that we are praying for Rupert’s family and each of you in his Jamaica Inn family.
    My wife, Waverly, and I had the pleasure of playing croquet with Rupert and another guest just a few months ago in November. We will always treasure the special afternoon that we got to spend with Rupert. He was a true gentleman with a great spirit and a warm, hearty laugh. We are blessed to have known him, and we know that you will miss him greatly. Rest in peace, Rupie!

  • (Mary) Anne Vulcano says:

    When I think of Jamaica Inn, I can’t imagine it without Rupert. He made us all feel like his favorite family members. He will always be in my heart.

  • Dees and I are so sorry to hear about Rupert. We were concerned about him on our last visit in October. He will be sadly missed by many.

    Iris Coxe

  • Bill and Lesley Waldman says:

    Rupee will be missed, he was one of the many reasons and one of the many people that makes it so special to return every year to the Jamaica Inn. May he Rest In Peace.

  • Sharon Creasy says:

    I am so saddened to hear of Rupie’s passing. He was such a kind spirit and always happy and smiling. He will be greatly missed by all who knew him

  • Trevor Horwell says:

    I am very deeply saddened to here this. I have been coming to Jamaica inn for over 35 years. Rupie was always part of the family. His demeanor and smile are unforgettable. I raise a glass to his memory and will always do so when I return to the hotel. God bless him. One of the best irreplaceable.

  • I had the “pleasure” of playing a lot of croquet with Rupie during our stay in June 2014.
    I actually won a game, and he was nearly impressed, but made sure that was the only one I would win in 2 weeks 🙂
    He taught me a trick shot and how to chip a croquet ball over one directly in front of it – something I thought was impossible.
    He’s a sad loss and our thoughts go out to his family and the wider Jamaica Inn family.

  • Charlene Bleakley says:

    So sorry to hear that he passed away. He was such a fantastic man! During our stay, he would remember what we liked to drink and come down with drinks in hand for us. He had such a lovely personality. May God bless him and his family.

  • Joe Kilpatrick says:

    Dear Jamaica Inn Family,
    We are so sad to hear of the passing of Rupie. I believe he was at the helm while we were just visiting this past fall. What a smile and command for the position he had. We cherished our experience with your hotel, the staff, and the atmosphere you all made for us. Losing any member of that team is a great loss. But when you lose such valued leadership from tenured staff like Mr. Davis, it casts a long shadow of sorrow. Our thoughts and prayers are with his family, friends and peers at the Jamaica Inn. May he be blessed on his next journey.

  • Karen and Peter (Canada) says:

    We had the privilege of visiting the Jamaica Inn several years in a row. It was always a pleasure to reconnect with employees like Rupert. He was courteous, friendly, and chill, but with a hint of mischief in his eyes. 🙂 Jamaica Inn will not be the same without him. It is lovely to see him being honoured here.

  • We are so sorry to hear of your loss. We just met Rupie on our first trip to your wonderful Inn a few weeks ago. He was one of the many friendly faces we will remember. He was always so pleasant and added to the memorable vacation we had. Please accept our deepest sympathies.

  • Linda and Terry Swift says:

    We didn’t get a chance to meet Rupie. I was looking forward to seeing him, as well as the rest of the amazing staff when we come down this June. Please know that Rupert and his family, as well as his family at Jamaica Inn, are in our prayers.

  • I knew Rupert for many years. He was kind and gentle and always had a warm smile for my wife and me. We played croquet many times, which was usually an exercise in futility and frustration (for me, not him). Somehow I always felt like I was being hustled, but in a good way. Over the years I think I only won once… looking back, I’m sure that he let me win. Once when my wife and I stayed somewhere else in Ocho Rios, we came over to the Jamaica Inn just to say hello to Rupert and Teddy. I’ll always have fond memories of my croquet playing friend with the warm, heavy handshake, rum punch, and bright smile.

  • Alexander & Lesley Howard says:

    My children had their wedding at Jamaica Inn May 2015 and I remember Mr. Rupie services each time we were in his presences , always at our call. My prayers are with his family in his heir to me of sorrows. May he Rest In Peace.

    God bless from the Howard Family

  • Rupert was truly emblematic of the friendliness of the JI staff. With his wickedly sharp sense of humor (once you got to know him) and great personality, he always made one feel like a friend, not just a visitor. I will miss my friend a great deal. God Bless, Rupert!

  • Louise de Verdier Madden says:

    We are so sad to hear about Rupert. He was always so warm, friendly and welcoming. Will always remember his croquet lessons and he will be dearly missed next time we visit Jamaica Inn!

  • Arthur A. Gray, Ph.D. says:

    This is so sad the Rupie died. My wife and I and a couple of friends was at Jamaica Inn this past May 2017. Rupie was the last person who took care of us on the beach. We always got such a warm feeling with him. Providing for us was his pleasure and made our stay that much more special. I know it is personal, but I wish I knew his age and how he died. Condolences to all of his family and to all of you at Jamaica Inn who shared time with him and cared about him.
    Arthur

  • So very sad to hear of Rupert’s passing. He was one of my many Jamaica Inn friends since 1986. I spent many happy times playing croquet with him and received many tips from him about the game.
    I will miss his friendly face and welcome home on my next visit…

  • NICOLE C SMITH says:

    All My Love to Rupert’s Family and Friends.My deepest condolences.
    Life is Eternal and he will be missed! I will never be the same…….

    Nicole C Smith
    New Jersey

  • My wife and I would like to extend our warmest and deepest condolences to the family of Mr. Rupert and his family at Jamaica Inn.

    My wife and I met Mr. Rupert early last year on our first trip to Jamaica Inn. I can’t thank him enough for making the day that I proposed to my wife even more special. He taught us both how to play the wonderful game of Croquet, and it was truly an honor to learn from his expertise. I know that we will think of him always the next time we pick up the mallet.

    Thank you, Mr. Rupert, for everything that you did for us that day. I know that you’ll be playing the beautiful game up in heaven and serving up the best cocktails to all the angels.

  • Karen & Ken Smith says:

    We’re so sorry to hear this sad news. Our thoughts and prayers go out to his family and loved ones. We remember him as such a warm and loving man who brought happiness to everyone who had he pleasure of meeting or knowing him. May his memory be a blessing, now and always, to all who knew and loved him. Sincerely, Karen and Ken Smith, Southlake, Texas USA

  • He was so nice. I remember him even pitching in to assist with the morning breakfast service. He would sometimes bring my morning breakfast tray and stop for a bit of a chat. My family is from St. Ann’s Bay and St. Catherine. Talking to him made me remember my family fondly. The stories of childhood and seeing his smile just gave my day an extra bit of joy. May he Rest In Peace. He will indeed be missed. But, in a little spark of that sunshine over Jamaica Inn, there’s a reflection of his beautiful spirit!

  • Regular Visitors with respect says:

    Rupie was one of the kindest, sweetest, down to earth people we’ve ever met. Even though we are just visitors who conversed with him a few days out of the year, we remember him fondly and with outmost warmth. His good humor, his calming and noticeable presence, his recognizable posture imbuled into our most precious memories. Deepest condolences to his family, and to his work family at Jamaica Inn. He will be utterly missed by all. I hope the light and peace he projected with his wonderful personality will be some of the warmest memories that continue. We will think of you often, Rupie. Rest in peace.

  • Terry and Mike Parrilli says:

    After we check-in, step into our room and unpack, the first thing we do is head out to the beach bar to reconnect with our Jamaica Inn family, Teddy, Georgia and Rupert. We hug, catch up on what’s been going on and now a dear friend is gone. We are so saddened by this huge loss of a wonderful gentle soul. Always smiling, offering a greeting each morning with a Planter’s Punch, wearing that “Rupert” belt buckle with the truck proudly all these years and then playing a croquet match or two in the late afternoon. I can’t imagine being on the beach without Rupert. We all were spoiled. This void is heartbreaking. He touched us all. May the croquet lawn always be smooth and manicured and the spirit of Rupert keep a watchful eye on the red ball going through the wicket and hitting the stake for a win. He was a flirt, the Jamaican father we all wished we had and a Jamaica Inn icon. Our lives were enriched because we knew him. Rest in peace, dear Rupie.

  • Marion Christoph says:

    This is terribly sad news. As recent guests to the Jamaica Inn a few weeks ago, I had the pleasure of having Rupert as my partner on the croquet court. We played against my husband (who played two balls) and I have to say I handicapped Rupert too much. My husband beat us (he is good) but Rupert had to try to undo many of my poor shots. He was a true gentleman with a warm sense of humor. What an honor to have met him and played with him. Our hearts go out to his family and to the staff at Jamaica Inn.

  • I loved to watch the silly guests who thought that they just might… perhaps, be able to beat Rupert at croquet. He would string them along most of the game and then, when it was necessary, fire off some shots that would leave them astounded for hours. He never gloated, always made it fun and had a great sense of humor. Rupert will never, ever be replaced, merely succeeded. It won’t be the same without him.

  • Samuel Crocker says:

    I can still bask in Rupert’s lovely smile and hear his resonant voice, whether at the bar or on the croquet court. He was a life member of the staff that honored Jamaica Inn’s long established traditions of perfect individual service that made the Inn such a wonderful place that has endured since we first visited in 1973. He will be remembered fondly by so many.

  • Laurie and Joe Gentle says:

    Sweet Rupert will be missed so much.

    He welcomed everyone as though he’d known them always and never let anyone get away with anything

    We will miss him very much and appreciated his friendship

  • Ed and Vanessa Stroud says:

    What a gentle and wonderful man he was. He will always have a very special place in our hearts and we will certainly never forget him. We had so much fun with him on the croquet lawn, at the beach bar and on the beach – his naughty jokes, his beautiful smile, his croquet skills and his care, love and laughter. We have a photo of Rupie up in our home which always makes us smile and it will continue to do so. What a legend! Rest in Peace Rupie, you were one in a million.

  • We’re so sad to hear this news. Rupie made our 2012 holiday so special as we play a lot of croquet in England. We played virtually every day at the Jamaica Inn, nearly always with Rupie if he was around. We thought we were quite good at croquet until we played with him – but he played his own ‘Jamaica Rules’, a bit of a mystery to us, but a lot of fun. He will be greatly missed, we’re sure by so many.
    Ron & Stephanie, England.

  • Monique Lentz says:

    We were so sorry and sad to hear about Rupie. He was so funny and sweet !!! We always enjoyed playing croquet with him for many years, especially on his team ! Everyone who met him over the years will really miss him.
    Monique and David Lentz
    Augusta, GA

  • Of over 100 visits to the Inn, Rupie was always my first and last visit at the beach bar. He tried mightily to advance my skills at croquet,but only managed to imprint the proper pronunciation. What a treasure for all at Jamaica Inn to remember and treasure the memories.

  • Dannet and Neville says:

    Rupie we are so saddened by your passing. What a pleasure to have known you. We will always remember the warmth and kindness you showed us. You will be truly missed. Rest In Peace and May God be forever with you.

  • Andrew&Jeannette Gasaway says:

    We are saddened to hear of Rubert’s passing. He was one of the staff members that greeted us on our first visit to the Jamaica Inn in 1975. I will miss his warm smile and hug when we saw each other every return visit. Andrew always looked forward to playing a game of croquet with Rupert.
    The master always showed him some new tricks. May he Rest In Peace knowing he will be greatly missed. The Gasaway’s

  • Not a lot of smiling until you got him on to the croquet lawn then you fond the real warm person.
    Condolence to the family

  • Paula and Bill Kroll says:

    Rest in peace Rupert. We will never forget our 20th anniversary at the Inn and our fond memories of you.
    Try as he might, Bill could never win a match against you. Your charm, patience and humor will leave a hard to fill vacancy at Jamaica Inn. See you in Eternity!

  • Andrew Turner says:

    We always stay in the cottages and would spend our beach time at the far end of the beach. The sight of Rupert strolling down the beach with a tray full of planters punch and the fruit smoothies at 11:30 every morning will always be etched in our minds. His patience with his croquet partners seemed limitless until the game was on the line. Rupert didnt like to lose!. His laid back demeanor was perfect in such a relaxing environment. We will miss him dearly.

    Andrew Turner and Leslie Black

  • Rupert “Rupie” was such a magical part of the Jamaica Inn. He will be forever remembered by us for his beach combing, punch in hand, and his unwavering patience with his skill in croquet. Loved his spirit and his timelessness that makes the Jamaica Inn our favorite place. With love to his Family. Heidi & Bill

  • Heather & Mervyn Ellison Nash says:

    Great sadness to hear about Rupie, and condolences to the family and Jamaica Inn. Although we have known him for a few years, he always greeted us , like a father would welcome home his children , Always had a tale to tell, and with Teddy they made a great pair.

  • Patrick and Maria Wade says:

    So very sorry to hear the sad news of Rupie’s passing and much appreciate you advising us.
    Rupie taught us the rules of croquet and mixed some wonderful cocktails. He will be very sadly missed.
    Our thoughts are with Rupie’s family and Jamaica Inn.

  • I have countless fond memories of Rupie over the last 15 years or so. I guess my most favorite two was just made over our last visit to the Inn in November, ’17. We had friends come with us on this last visit. The last croquet match we played was with Rupie and our friends. I was always, always Rupie’s partner over the years. We had so much fun laughing and joking. And yes, Rupie and I won! Although we’ve played many, many croquet games with Rupert, it felt like more fun than usual. The other sweet gesture was him taking the extra time to come and find us for our daily Planters in our cottage on the morning that our friends were to go home because he didn’t see us down at the beach. It was hot and sunny and we asked him to sit down, drink some water and we had the most lovely conversation with him. Again, he left us with hugs and laughter. I will miss him. I truly loved him. He told me all about his family. We shared recipes. We told jokes. He sent me home with vinegar he made that I used for a year! I’ve never been to the Jamaica Inn without him there. Not sure what it will be like to not get daily hugs from the man who gave so much love. We, too, extend our deepest condolences to his family and all who loved him.
    With love to you all,
    Nicole Swift

  • Carol Millhouse says:

    We are so sorry to hear of Rupert’s passing. We just met Rupert this past December on our first stay at the Jamaica Inn. He was always so very friendly and had such a kind, warm smile for all. He taught my husband to play croquet and they even won their match. His presence will be greatly missed by us on our next visit to the Inn, and, as well, I am sure by all others who knew him.

  • Scott Johnson says:

    Rupie will be sorely missed. We have many fond memories with him and the bar staff playing croquet and exchanging stories.

  • Jamie Abraham says:

    So sorry to hear about Rupert. Had so much fun playing croquet with him this past October. What a wonderful person. He will be missed. R.I.P Rupert Much Love

  • angela roberts says:

    This is such sad news . We have been coming to Jamaica Inn for over 20 years & Rupie was always there to welcome us back with a warm hug . Not to mention that he turned my husband into a pretty good croquet player , they would play every afternoon except his day off . We will truly truly miss him . Angela Roberts .

  • Don and Joann Leavenworth says:

    Rupie was most notable to us for his outstanding talents and coaching in Jamaica Inn croquet and for his very able bar tending skills. He will be greatly missed.
    We would appreciate knowing when his celebration of life will occur.

  • I am so sorry to hear of Ruperts passing. He was a delight welcoming us to the Beach Bar.
    Rupie was always smiling and at his best teaching the game of croquet,and partnering with those of us less talented.I always wanted him as my partner.
    I send my sympathy to this family and keep them in my thoughts and prayers.

  • So sorry to hear of Rupert’s passing. My wife and I enjoyed talking with him on the beach over the past 20 years that we’ve been coming to the hotel. I am glad we got a chance to catch up with him this past December. Please pass along our condolences to Rupert’s family and his colleagues at the hotel.

  • Linda Collins and Scott Ricker says:

    Scott and I are so very saddened to hear this news. Though it was our first visit to the Jamaica Inn, we felt you all became like family. Rupie was such a genuine and kind person. He will be sorely missed. Our condolences to all.

    Love,
    Scott and Linda.

  • Frances & Bob Smith says:

    So sad to hear about Rupie, we were looking forward to seeing him again in May. Such a kind, gentle man with special powers to know just when a Red Stripe was needed. Deepest sympathies to all his family, he touched many lives and will be sadly missed by all.

  • Very sad news! We met him last year and his “Dirty Bananas” are unforgotten. Rest in peace, it was a pleasure to met you!

  • When Mista and I arrived at the Jamaica Inn in December, it instantly felt like home. The owner came down to greet us immediately and to welcome us to his family. Drinks and cold towels were immediately served to us as our luggage was being carried to our room. The staff waited on us hand and foot with a smile each and everyday. As we were getting ready to leave, they all wanted to make sure that we enjoyed our stay. The same way the owner greeted us upon arriving, is the same way he came to say goodbye. Only this time he came with a going away present. It was a beautiful jewelry box, with a hand painted picture of the Jamaica Inn on top. He hugged us good bye and said…I will see you next year My Family. Inside of the box was a note that said, My name is Annabelle and that I should fill Annabelle with all of my lovely trinkets. Underneath that, Love Always, Your Jamaica Inn Family. Since arriving back home, I have constantly received emails about how my Jamaica Inn family misses me, emails welcoming back home, etc…UNTIL tonight….I got one of the saddest emails ever. An email telling me that Rupie had passed away. Rupie was the first person I saw every morning and every night. A smile so bright that it was truly infectious. I took pictures with him on my last night there..He took such great care of me…that I tipped him $20 every night. Not for his service but for actually talking to me like I’m not there to be waited on. For actually caring and asking questions about me or us in general. I’m truly sad that on my next visit Rupie won’t be there. It doesn’t matter how long you’ve known a person…BUT if they cross your heart in the RIGHT WAY…They will forever stay right there. Rest In Heaven Rupie. I most certainly, will neva forget you.

  • Kevin and Amanda edgar says:

    The most charming man , he always delivered our drinks with a lovely smile and charming quip ! Such an asset lost .

  • julie , Ed, Evan and Jennifer Winston says:

    We are so saddened to hear of “Uncle Rupie’s” paling. We were at the Inn in December (last month) and shared hugs along with our usual joking! We have been going to the Inn for over 40 years and always looked forward to Rupert’s smile and kind words…always asking about the family by name and asking to see photos! He certainly was a part of our stay every year! He will certainly be missed by the entire Winston family!

  • Mary Bergstresser says:

    We extend our sincere sympathy to Rupert’s family. We remember him well, at the Main Bar at Jamaica Inn and at the beach bar. He was always so pleasant and a real gentleman.

    Mary and David Bergstresser

    • Thank you all for your kind words, Rupert’s passing was a great loss. We’ll ensure to pass on your sentiments to the rest of our team.

  • Rupert was a lovely man, the spirit of old Jamaican chivalry. We will miss him on the court and off. Our deepest sympathy to his family and friends.
    Mona and Rose

    • Dear all, today is a very special day for Rupert and his wife and children. The Jamaica Inn will rightly name the croquet lawn after the master of the lawn, Rupert. The celebration of his life starts at 3PM today on the lawn. I have been honored being asked to say a few words about this wonderful man as I am one of his long-time prey and victims on the lawn I wish I could read to Mrs. Davis and all at the gathering, the 99 posts that have gone before mine plus 52 comments (with 263 likes) on Facebook. I will ask Kyle to print and give them to Mrs. Davis. The best to all, Barry

  • Nancy Demorest says:

    Julia, Stephen and I would like to extend our condolences to Rupert’s wife and children. We were so fond of him. When Jules and I were there last April, I was so happy to see him again after so many years. When I was summoned to the office at one point and was hurrying up the steps, I passed him and whispered conspiratorially that I’d been “called to the office” and Rupert looked at me as if I were a misbehaving schoolgirl and said “What’d you do?” We always had a good time together, and was one of the big reasons Jamaica Inn was so special to me. I have wonderful pictures of him and Julia from this last trip and will always remember him.

  • My husband and I would like to extend our deepest condolences to the family of Mr. Rupert and his family at Jamaica Inn.

    My husband and I met Mr. Rupert 12 years on our first visit to Jamaica Inn. We loved his wit, quick to responses and skill at both mixing a thirst quenching drink and his favorite game of croquet. He taught us both the proper rules of this game, which we then went home to Seattle and taught our family in annual croquet tournaments at our family reunions. I then started a North Bend (cottage district) croquet tournament for couples. Rupert guided everyone on exact “Rupert’s Rules” One time one of the wives couldn’t or did not want to play, so, Rupert played as a sub. Needless to say, they won! I had a trophy made that was engraved each year with the winners. I am so glad we have his name on our trophy and were here to show the family during the memorial/dedication of the croquet court. It was such an honor to learn from Rupert’s expertise. We had the “North Bend” tournament a couple days ago, and we decided to rename our tournament the Rupert Memorial North Bend Croquet Tournament. I will take the trophy back to the states to have engraved. We all will remember and miss him dearly especially while playing croquet. Just as the tournament was to begin, Kyle and team members, brought down to the court the new croquet set, new mallets, balls and stake that Rupert ordered just prior to his passing. We dedicated the stake to Rupert and hammered it into the ground. Rupert’s famous black ball was retired in his name.

    Thank you, Mr. Rupert, for everything that you have done for us. We know you are in heaven playing with angels and drinking a refreshing drink with them……

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