It was no secret that Guy Ray used to really enjoy match racing. Not only was it a time when he could show off his fast horses it also gave opportunity to demonstrate his wit and understanding of people.

Match racing was fun. It was the only way a person could make much money with your horses back then. Guy Ray’s reputation of having the fastest horses around kept growing. It became difficult for him to get a match. He would even load up the old stock truck with five or six horses and send the neighbors with the horses to match at Altamont, Nowata or wherever they ran while he sat at home. Guy Ray had more fun match racing than just about anything he ever did.

June (Oscar) Jeffers was one of the leading breeders of racehorses back in the ‘60’s. He owned Mr Bar None, the sire of Bayou Bar. He owned a Ford dealership in Wagoner, Oklahoma. Guy Ray and June seemed to have that friendly rivalry between them, each thinking that they raised better horses than the other. Of course, back then; the way to resolve any disputes of who had the faster horse was simply to match ‘em up. Scheming and plotting was all a part of getting the next match race set up. So it came. 

In the late 50’s, June had a little horse called NR Negraleeta. She had quite a reputation matching across Oklahoma and Arkansas. The word was out that he had something Guy Ray Rutland couldn’t outrun and he would put up as much money to prove it as it took. Back then, it wasn’t necessarily the money that generated the most match races, but the bragging rights. A few negative remarks about someone or their horse made for an interesting race. Guy Ray had a daughter of Gold King Bailey named She’ll Do It. She hadn’t run much yet officially, but Guy Ray knew she had talent. One Sunday afternoon he and son Cliff, his jockey, loaded her up and headed to Pryor, Oklahoma to the races. Guy Ray really didn’t want to run against NR Negraleeta but if June would give him daylight then he would take a chance. It didn’t take long with June bragging about his horse that the match was on.

They each went back to their trailers and took care of whatever business they did back then…and got their horses saddled. As they got to the track Guy Ray leaned over to leg Cliff on and quietly whispered “Just run lapped up on him. We’ve got daylight.” Cliff nodded and rode off to warm up. When the dust settled, NR  Negraleeta had won the race, but only by about ¾ of a length. “My horse didn’t get away good,” cried June Jeffers. “I want a rematch.” So a rematch was settled on for two weeks from that day. Guy Ray was always “nice enough” to allow someone a chance to get their money back. He wanted to win fair and square, but Guy Ray would still need daylight if he was about to run against such an outstanding horse.  It was agreed.

So two weeks came and passed. This time as Guy Ray legged Cliff up he whispered “Let him outrun you about a half-a-side.” Cliff grinned and jogged his mare down the track. They loaded up and away they went, NR Negraleeta winning by a solid half a length. Jeffers was furious, “Something had to have gone wrong.  How lucky can that Rutland be?” Guy Ray, offering his feelings of disbelief, said “I’ll tell you what June, I will just run you for double or nothing, heads-up.” June Jeffers couldn’t believe what he was hearing. He had already outrun this mare twice, and now Rutland wanted to run for that kind of money without having to spot him daylight. The match was on.

So came two weeks later. This time, the word had circulated around eastern Oklahoma, Kansas and western Arkansas that there was quite a match race going on. A big crowd gathered beside the football field in Pryor to watch history being made. A lot of side bets were now being made, everyone wanted a piece of the action. Same preparation took place, this time as Guy Ray threw Cliff up he said “Let her win, but make it as close as you can, a nose would be good.” Cliff knew that he had a lot of horse under him but to gauge that and allow her to win by such a close margin made him a little uncomfortable. That was quite a lot of responsibility for a 16-year-old kid. But he would try. What a horse race it was! The crowd went wild. She’ll Do It won by a slim nose! The horses hadn’t even gotten back to be unsaddled yet and Jeffers wanted yet another rematch. Guy Ray obliged. Two weeks later She’ll Do It won by a little over a head. June Jeffers was ready to tuck his tail and walk away when Guy Ray went up to him and said “June, I don’t think this has been quite fair. To show you what kind of a guy I am, I am going to give you a chance to get all your money back. I am going to match you once and for all and I am going to give YOU daylight.” Jeffers thought for a minute of how close he had come to winning every bet they had made over the past month and finally agreed to one final race between these two.

Of course you should be able to guess the ending by now. Guy Ray legged Cliff up this time only to say, “Let her run today, Son.” She’ll Do It and Cliff outran NR Negraleeta by over a length and a half. The huge crowd that was on hand couldn’t believe what had just happened. June Jeffers went up to shake Guy Ray’s hand and said “Rutland, that’s enough. I am going to stop before you own that Ford dealership.” They both chuckled and went on their way. They parted friends but never did have any more match races between the two of them.

Never was a time when Guy Ray would ever make an enemy. Whether he won or lost the race, he always made sure that a friendship wouldn’t be affected.  The love of the game meant too much to him for it to be ruined by hard feelings. People would enjoy listening to his antics and humor that made him the likeable person he was. But he seemed to also have that knack for knowing just what needed to be said or done to get that “next match set up”.