As horses file into shed rows, consignors proudly hang their signs, and buyers shuffle into the pavilion for the Keeneland January Horses of All Ages Sale, auctioneer Scott Caldwell will take to the stand for his 48th year of selling at the historic venue.
The Caldwell name resounds from the very walls of the Kentucky auction house, with Scott's father, Tom, having joined the team back in the late 1950s. However, the family's history of auctioneering goes back even further.
Caldwell's grandfather owned multiple stockyards in Southern California, and naturally, he invited his son to participate in the venture—with Tom gladly obliging. While working there, he met one of Keeneland's first auction directors, George Swinebroad.
"When dad was very young, what happened was George had a tough night, had a little bit of a bug, and they started calling around (for backup) when they were doing the major sale in California," Caldwell said. "Dad being 'C' under Caldwell on the list of auctioneers was, if not the first one called, then the first one who accepted.
"At that point he had ridden lots of horses but never sold horses. He and George got to work together, and George said, 'You're my boy.' The very next time Keeneland came around, he was there and stuck around ever since, until his passing (in 2001)."
After kicking off his career in 1947, 10 years later, Tom became first assistant to Swinebroad, the head auctioneer at Keeneland in 1957. He took over leadership after Swinebroad passed in 1975.
"My dad was a legend in this business. He brought a lot of maturity and integrity that (the role) always had, but he pushed the envelope with people to build relationships," Caldwell said.
Scott, along with his brother Cris, joined the team that same year his father took over.
Born and raised on a ranch in California, Caldwell has dived into several different professions over the years, including working in the surfing industry as a sponsored athlete and later owning a surfboard shop. However, auctioneering was the passion that stuck. He eventually attended the Worldwide College of Auctioneering in Mason City, Iowa, where he spent two weeks learning how to announce at schooling auctions and then live auctions.
"I would say the auctioneering business is a lot like doctors (in that) it seems that doctors' kids end up being doctors. and I think a lot of auctioneers' sons enjoy following in their father's footsteps, as did I and my boys. Nepotism in our family is rampant," Caldwell said with a smile.
Both of his sons, Ramsey and Kenny Caldwell, work as automobile auctioneers in California.
Heartbreak struck the Caldwells in 2001 when Tom lost a battle with pancreatic cancer at the age of 72. The same disease claimed Cris in 2020 at only 63. Despite those losses, Caldwell returns time and time again to the place that holds countless memories of his family.
"It was extremely tough when my father passed away. It gets me pretty good. He was a legend in my mind, and my brother the same. Cris had nothing but good things to say about this place and loved it dearly, as did my father," Caldwell said.
"I often say that if they didn't pay me here, I would still come. It's in my blood, and I love it. I love the consignors. A lot of these people have become close, personal friends, and they shared in both Cris and Dad's death as well. Lots of people reached out to my mom and myself and it was very special."
One person who shared in Scott's loss was track and sales announcer Kurt Becker, who has been friends with Caldwell for most of his life.
"Our two families came to know each other through the Standardbred business," Becker said. "My father worked Standardbred sales as an announcer, and he and the Caldwell family worked them together... I remember it was August of 1978 when I met Scott for the first time because he came to our home state of Illinois to work a Standardbred yearling sale.
"I was nine years old, and I'll guess Scott was in his mid-twenties... Here's a guy that's a good-looking, popular young member of the horse business and he comes along and is willing to let you sit next to him at dinner with your folks and pays attention to you, it makes you feel like you've been accepted into the club, so to speak. I remember how generous Scott was to me at a very young age, and I've never forgotten it."
In November of 2021, Becker lost his father, Carl, a well-known and respected track announcer in Standardbred racing, after a brief illness. Kurt returned to Keeneland in January of the following year and credits his relationship with Scott, as well as the rest of the team, for his success through the difficult time.
"There was a quiet reassurance in knowing there were other people around that table, other people on that auction stand," Becker said. "They've been there, they know what it's like, and the example they have set by being strong and going forward, that helped me as much as anything."
Along with handling grief, Caldwell says another difficult part of his job has been not feeling satisfied after a sale. He says he often thinks he could have done something different, which would have created a more positive ending.
"There's a lot of sleepless nights when you re-think about what you did during the day," Caldwell said. "I have a lot of nights where I think to myself, 'If I would've just done this or done that'... Especially when the consignor thinks (he/she) has a big horse, you try to sell it like a big horse."
Despite the valleys which will evidently come with any profession, Caldwell, who will turn 72 in 2023, reflected on some of the higher points of his life spent in the industry. He recalls seeing horses such as Knicks Go , Animal Kingdom, Mitole , Drefong, and Justify go through the ring.
However, Caldwell has always kept humility at the core of his profession. He says when horses go on to perform well on the track and make names for themselves, he only thinks about the sale and wonders if he did the best possible job that he could.
"Selling Justify was just like any other horse in the ring. As it was, he brought half a million dollars, and turns out he was worth $100 million. Probably the guy that sold him thinks I did a pretty poor job. It's probably one of those things that keeps me up at night.
"That's what's so amazing here. You sell so many champions. If you looked at the average race call in Southern California at the end of the day and the top three horses at least one, if not two, had been sold at Keeneland at some point in their career... What an amazing place to work for."
Caldwell has also kept his family at the center of his work. He commutes from California to be at Keeneland as well as other auction venues around the country. His wife Leslie often joins him, and as much as he can, he attends events for his grandchildren. When he is not working, he lets down by fishing and hunting.
"There's very little ego in that man. Here's a guy who's got more seniority than pretty much any of us, yet he never holds that over our heads. I've never heard him pull rank on any of us," Becker said. "He values our input; he values our opinion. He just enjoys being part of the team. I think it's the lack of ego on Scott's part combined with the way he priorities things in his life, putting family first."
Keeneland president Shannon Arvin said the Caldwells have been instrumental in building the atmosphere on the sales grounds.
"The Caldwell family, beginning with Scott's father, Tom, and later with Scott and his brother, Cris, helped establish Keeneland as the world's premier sales company," Arvin said. "Scott combines expertise, talent, and professionalism with a passion for the horse and a desire to provide consignors and buyers with the best environment for success. We feel very fortunate to have Scott as an important part of our Keeneland team."
Caldwell echoed Becker's thoughts regarding the team element, recognizing that every person involved does their part to make each day, down to the last minute, go as smoothly as possible. Other important elements of the Keeneland team include vice president of sales Tony Lacy, director of sales Cormac Breathnach, and director of auctioneers Ryan Mahan.
"It starts off with Shannon and then Tony and Cormac, Ryan, and all the rest of us, and then it gets down to the ringmen," he said. "At times you feel like an octopus. You're up at the top, but you have all these tendrils... It's seamless, I think."
As yet another year at Keeneland rolls around, Caldwell will be where he belongs and is most at home—on the stand. Although his family may not be up there with him any longer, he still carries his father's words with him and makes sure to live them out.
"He said, 'You know, son, I've got money in the bank, and it will not buy me out of this pancreatic cancer. I wish I'd spent more time with you, your brother, your sisters, doing family things.'
"That stuck with me. From that day forward, my wife and I have taken whatever family we have...We go somewhere for a week," Caldwell said. "Mom and I pay for it. If we beg, borrow, steal the money every year, we get it done. It is so important to me."
