Widows Freckles and Austin Shepard
Widows Freckles and Austin Shepard together made an impact after the stallion's aged-event career.

Saying Goodbye to Widows Freckles, a family’s ‘Dream Horse’

Top cutting competitor and sire Widows Freckles has died, those closest to the stallion announced on Tuesday afternoon.

The sorrel stallion was 26.

“We received the news this morning that our boy Widows Freckles, or as his family knew him, ‘Obi,’ was laid to rest,” Lauren Middleton said through a social media platform. “It is hard to put into words what this horse meant and the impact he made on our family and for the Shepard family.”

Obi, by the renowned Freckles Playboy and out of The Widow Wilson (by Son Ofa Doc), had an Equi-Stat record of $122,981. He flourished under the ownership of Robert and Debbie Middleton, who purchased him from Sam Wilson in 1999.

Obi was, Lauren Middleton said, “Dad’s dream horse.”

“Dad saw him as a 4 year old and loved him from day one,” Lauren said. “He had to have him and was determined to figure out how to buy him.”

Since 2006, Obi has lived under the ownership of David and Stacie McDavid of Fort Worth, Texas. 

The Middletons took Obi to Austin Shepard, then a young trainer, after his aged-event career. Since 1999, Obi won $196,955 working under mostly Robert Rust, Shepard, and Lauren and Robert Middleton in the non-pro divisions.

His last run was a dandy, at the NCHA World Championship Finals, where he turned in a field-best 228 for Shepard for a check of $7,400.

“He was probably one of the grittiest, an old-school type tough kind of horse,” said Shepard. “As sweet as he could be to be around. He hurt his hock one time really bad. He fractured his hock. I got done showing him, we took the boots off of him, didn’t see a thing. He didn’t start limping until we got him back to the trailer. That’s tough. Tha’s like you breaking your leg and walking on it until your adrenaline wore off.” 

Shepard remembered being “tickled” to get the opportunity the Middlletons gave him on Obi, who between his life as a performer and a sire, “sure helped me get my foot in the door” in the industry, Shepard said.

Of Shepard, Lauren Middleton wrote: “Dad asked him about hauling Obi down the road for him a little bit to see what they could accomplish and the rest is history! They had many wins and Obi made some incredible memories for the Shepards and for us! He carried all of us to Championships during his career.”

That relationship with the Middletons, Shepard said, began because of Obi. “It’s like our two families are families and it all started because of that horse.”

Obi was a winner as a sire, as well, siring 83 off-spring performers for a total of more than $1.5 million in show pen earnings. 

“He passed on that same style to his” foals, Shepard said. “They were low headed, stopped hard and cowy.” 

Widows Intentions, a 2000 gelding trained by Shepard, is Obi’s top performer having earned $353,065 in his career, according to Equi-Stat.

“If he’s not the best gelding I’ve ever ridden, he’s in the top two or three,” Shepard said. “He may be as good a horse as I’ve ever had.” 

Shepard’s first victory at Fort Worth’s Will Rogers Coliseum was on Widows Intention at the NCHA Super Stakes 5/6 Year-Old in 2006.  They were the last to go in the finals, Shepard recalled.

“A typical run like his daddy. Work two cows and hold it to the buzzer. They didn’t mind a challenge.”

Smart Freckled Cat, a 2007 gelding, had an Equi-Stat record of better than $135,000, and Widows Tears, a 2000 mare, earned $92,741.

“It is a sad day, but at the same time we think back to how much he blessed us, and there are not many horses that can do that for not one, but two, families,” Lauren Middleton said. “We want to thank the McDavids for taking such wonderful care of him and Clint Allen as well. 

“We know he lived his best life even after he left our home. We will never forget him running in our front pasture. Dad’s dream horse. Rest in Peace, old friend. Until we see you again!”