His coat may be fluffy and faded from spending his days grazing in a paddock with his miniature horse companions, but at 30, Diplomacy’s eyes are bright. Even after years of retirement at show jumper Georgina Bloomberg’s Gotham North in North Salem, New York, he still carries the regal expression that helped him win so many junior hunter championships at the country’s biggest horse shows.

“He’s just always been one of favorite horses of all time, not just because he accomplished so much and won for me and was such a great horse to ride, but mostly because I just really love him,” said Bloomberg, 35. “We’ve always had a great relationship. That horse gave me so much, so it’s nice to be able to give him the retirement that he deserves.”

Diplomacy in his retirement. Photo by Jump Media.

Bloomberg bought Diplomacy, or “Henry,” a bay Thoroughbred gelding (Presto Lad—Tudor’s Joy), in November 1997. “I’ll never forget that the first time I laid eyes on him; he took my breath away. I knew at first sight that this horse was special and that my life was about to change with him in it,” Bloomberg said. “He was so incredibly beautiful. I still whisper that in his ear sometimes.”

Bloomberg and Henry won championships in the large junior hunter, 15 and under, division throughout 1998 and picked up their first Pennsylvania National tricolor that fall. In 1999 they claimed the Winter Equestrian Festival (Florida) circuit championship and the grand junior hunter championship at Devon (Pennsylvania). They collected tricolor after tricolor all year, ending the year with the large junior hunter, 15 and under, championship honors at the National Horse Show (New York). In 2000, they were WEF circuit champions again, champion at the Capital Challenge (Maryland) and reserve at the Pennsylvania National.

Diplomacy and Georgina Bloomberg jumping in Wellington, Florida, in 2000 during the gelding’s heyday. Photo by Molly Sorge.

“He was so scopey; his jump was incredible. He was so big and long that he had a very unique rocking canter. He felt magical. I remember the feeling of being on him and just knowing I was sitting on incredible talent,” Bloomberg said.

But Henry wasn’t a push-button horse. “He was always tough. He was a hard horse to ride, and he made you work for it. If you let your guard down, he’d buck you off,” Bloomberg said. “I have so many great memories of him challenging me—and of him bucking me off!—and then coming back the next show and winning. He always made you appreciate the victories because the week before you might have been in the dirt after getting bucked off.

“He was one of the horses that when you put the work in and deserved to win, it would pay off, but you had to put the work in,” she said. “I appreciated the opportunity to ride him every time. Whether we won or not, I knew he was special and that I was lucky to be on him. He was the nicest horse I had ever sat on. He had the potential to win it all if you worked hard and rode well, and I took that challenge seriously and never took my opportunity with him for granted. He made me realize that if you work hard, eventually it will pay off.”

Diplomacy on his way to one of his many Devon (Pa.) tricolors. Photo by Tricia Booker.

Henry picked up more championships in 2001, but at age 13, he was slowing down. The Pennsylvania National that year would be his last show. He and Bloomberg were called back to jog first in one of the large junior, 16-17, classes, but Henry wasn’t quite even.

“I had my other horse, New Hope, in the class as well,” Bloomberg said. “Erin Stewart was jogging him for me, and I jogged in with Henry. They made us re-jog and then ended up excusing me for him not passing the jog.

“I remember walking out of the ring with him, and Erin said to me, ‘Do you want to switch and get the ribbon with New Hope?’ And I told her, ‘No, he got me in here, the least I can do is walk out with him.’ I wasn’t going to hand him off because he didn’t win that last blue ribbon. Even at a young age, I realized the importance of how much he’d done for me. Standing by your horses when they don’t win is as important as when they do. I was just as proud to walk out of the ring with him that day as I was to ever walk in and get a blue ribbon with him.”

Diplomacy with his current companions, Lola and Harley. Photo by Jump Media.

Henry spent a few years turned out at a farm in Virginia before Bloomberg added on to Gotham North and shipped him to North Salem for the rest of his retirement. “When we bought that farm, I always wanted to have as many of our retired horses as possible there,” said Bloomberg. Henry shares a paddock with two rescues, Lola and Harley. Bloomberg rescued Lola from an auction, and the mare turned out to be in foal. “Henry spends all day eating grass, and he still gets plenty of treats,” said Bloomberg. “I visit him as much as I can and give him his favorite treats, Ginger Snaps and Cracklin’ Oat Bran.”

The Chronicle will be on-site at the Pennsylvania National bringing you beautiful photos, interviews and more, so check back throughout the competition. Don’t forget to follow the Chronicle on Facebook, Twitter and Instagram @Chronofhorse. We will have full analysis of the competition in the Nov. 5 issue of the magazine.