Remembrances: Olin Gentry

Accomplished horseman Olin B. Gentry passed away at the age of 51 Saturday and left behind many friends within the Thoroughbred industry. A fourth-generation horseman, “Olee” Gentry was known for his engaging personality and passion for horse sales. A number of remembrances from Gentry's friends, family and colleagues were shared with the TDN in the days following his passing.

Olin would always refer to me as the “luckiest girl alive.” As a joke of course. He thought I had a lot to deal with holding his hand. I really was the luckiest. I will miss his hands and the power to calm and hold me close. The love and respect he showed to me was unbound. His cuddles and hugs were like grandma's lap. He was true blue. My love, my heart, my person. There is not enough space to write all the ways Olin was the love and delight of my life. I am the luckiest girl alive to have held him so closely. –Athena Gentry

Olee, It's been a wildly successful partnership all these many years, but more importantly an amazing and enduring friendship. Thank you!!! I already miss you. There will be a smile on my heart every time I think of you. Good mood, one with each other. –Tom Van Meter

Olin was a great friend, great horseman, and heart human being. I will miss him sorely as a friend and partner. –Spider Duignan

Olee was a dear friend, a partner, my confidant, my biggest cheerleader and supporter, my buddy, my personal comedian and most of all my “true friend.” His dry wit and great stories kept long days at the sales fun and entertaining. I love Olin Gentry like a brother–I had his back and he had mine.  I will never forget all that he taught me about the Thoroughbred business and how to be a friend. Thanks for being a “star” in my life, Olin Gentry. Cheers my sweet friend. –Renee Dailey

For 42 years, Olin has been been in my corner–loving, supporting, and overrating me every moment. He made me better than I was, and I have no idea how to navigate this world without him. –Marty Charters

A lot will be said this week about Olin, the horseman, and his many accomplishments. I have found great peace in reflecting on Olin, the humanitarian. Olin cared very much about people. He was equally comfortable conversing with a groom as much as a prince. Olin was kind and generous to all people, but especially horsemen. Many found him to be generous in their time of need. Olin had agreed to become an organ donor, and though he is now gone, his final unselfish gift was to extend the lives of others through his organ donations. This typified who Olin was. –James Keogh

Olin was one for the ages. We shared a birthday and had an annual competition on who would be first to wish the other happy birthday. He inevitably would text me at 12:01 am to win! Olin had a unique insight into human nature and made me laugh about his observations on people and life like few others can. He is gone way too soon. –Dan Pride

I could listen to Olin Gentry for hours. He was a skilled story teller, a character who never lost his sense of humor even on the darkest days, and while verbalizing the most complex deal, he would shift gears and dead pan the most embarrassing of human experiences. This was always followed by, “the grin.” He enjoyed imitating those he admired and I will never forget him explaining a wee bit of sculduggery in his Irish accent. He was confident and gentle and once critiqued me in classic street language intermingled with Ivy League grammar. He had a computer for a mind and was most proficient with numbers, providing multi-digit sums faster than my calculator. Olin loved his family and friends and told me many times that “O2” was his greatest joy in life. He also loved the Big Blue, but horse trade was his passion. I am extremely grateful to have known Olin and I worry that I may never laugh as hard, or appreciate a juicy tale, again. –Tony Cecil

Olin grew up under horsemen. He absorbed more knowledge of the horse business then some people may know. He was compassionate to his animals and friends. The horse community has lost another good one way too soon. –Chuck Kidder

When you spoke to Olin, what seemed like a five-minute conversation would be an hour-long talk about life and horses. What hurts the most is the potential of the future–the passion and the incredible gifts of spirit and joy he possessed. I can still hear his unique voice in my mind, and I think that the best way to sum up what Olin meant to me is to say that my life was better because he was in it. –Carrie Brogden

I am absolutely devastated at the passing of my Great Friend Olin Gentry. Olin was a great horseman, but he was also the best Deal Maker I have ever been associated with. Simply put: Genius. He was one of a kind and left us way to early. It was my privilege and honor to have know Olin for the last 25 years. –Omar Trevino

Olin was a true friend and great partner who will be greatly missed. He was the epitome of a Kentucky gentleman and was such a great horseman. The lineage carried through from his father and grandfather inheriting the ability to market the highest quality thoroughbreds. It always amazed me the innate ability he had to judge the current conditions of the TB market.  He was so knowledgeable of pedigrees and had a great eye for a horse. Business aside and most importantly, Olin was such a gentle and kind soul. –Scott Dilworth

We had our differences and when Olin wasn't invited to my small wedding, he called me on the morning of the ceremony with a smile in his voice, and we talked for two hours. Olin loved to quote lines from movies to drive a point home and then howl with laughter. He was a good friend who would do anything for those he loved. –Tom Clark

Olin and I met as students at UK in 1985. This Wisconsinite was exposed to the Thoroughbred industry through Olin's associations and education with his late father Tom Gentry, the late great Charlie Whittington, Payton Stud and the late John R. Gaines. We were roommates, friends, confidants and business partners for 34 years. Some 1200+ horses later, I thank this incredible horseman for taking me on a wonderful ride in a wonderful industry. I will miss you dearly my friend. –Michael Schmeling

Six years ago, I met Olin Gentry when he interviewed me for a position at Gaines-Gentry Thoroughbreds and I was hired. I knew nothing about the horse industry at all other than going to Keeneland during the spring and fall meets. I learned so much from him. The Thoroughbred industry was in his blood and you could tell that he loved doing what he did. A few years later, after leaving Gaines-Gentry Thoroughbreds, he became a client of mine and I got to know him on a friendship level as well. My memory of him will be a man that loved horses and loved his friends. He had a very kind heart and I will miss him terribly. My thoughts and prayers are with his family and those whose lives he touched. –Jeanette Patrick