Bobby Cruickshank (Born, Grantown-on-Spey, Scotland, November 16, 1894; died, Delray Beach, Florida, August 27, 1975.) Known as “Wee Bobby” or the “Wee Scot” because of his small stature (5-foot-2 to 5-4), Cruickshank served in the British Army in World War I. Captured in action by the Germans, he was a prisoner of war and later successfully escaped with the help of a local woman he had befriended. He then rejoined his regiment and saw out the war with distinction as Sergeant RA Cruickshank.

Once the Great War ended with an armistice on November 11, 1918, Bobby returned to Scotland and resumed his promising golfing career. With the success he was enjoying, Cruickshank turned professional and left Scotland for America in February 1921. He rose to prominence in the United States after reaching the semi-finals of the PGA Championship in 1922 and 1923, but lost both times to eventual champion Gene Sarazen. Cruickshank was also the runner-up in the U.S. Open in 1923 and 1932, won by Bobby Jones and Sarazen, respectively.

As one of the star names in golf, Cruickshank was well placed to take advantage of the extra cash ($300 per appearance) that could be earned by way of exhibition matches. The Scotsman’s flair and colorful game brought him to Oklahoma City in the fall of 1924. On Sunday, October 12^th Cruickshank and his traveling companion Al Espinosa played in a best-ball match against Bill Creavy and Harold Long.

During that match, my 14-year-old father, who was the No. 1 caddie at Oklahoma City Golf and Country Club, was assigned the honor of toting Wee Bobby’s golf bag. As time passed, Dad’s admiration deepened for Cruickshank and he caddied for the Wee Scot every chance he could. In those days it was considered a privilege to caddie for a player the likes of Cruickshank. My father said that the Scotsman was the first truly distinguished golfer that he was able to observe. Cruickshank was a magnificent player with a beautiful style and my father paid particular attention to the distinctive and artistic way in which he played. Dad is quoted as saying, “But, Cruickshank too, experimented with his game and taught others what he had picked up along the way.”

Bobby Cruickshank was an active member of the P.G.A. tour from 1921 to 1950, winning 20 tournaments. His greatest year was 1927, when he won the Los Angeles and Texas Opens and led the tour with winnings of $17,800. In 1967, Cruickshank was elected to the PGA Golf Hall of Fame. When his competitive career was over, he took on a series of pro jobs across the country, until his death at age 80.

Without a doubt, Cruickshank’s was no ordinary life. He lived it without regret, and remained philosophical about his “near misses”. He made this clear in the 1974 interview: “I’ve no regrets. We had our chance, that’s the way the Lord makes it. I think things work out for the best. If you win, you win, if you don’t, you don’t. It’s fate’s work, you see.”

Bobby Cruickshank (left) and Thomas (Tommy) Dickson Armour were fierce competitors on the golf course and lifelong friends off it. In the above photo, Cruickshank and Armour are shown after turning in 66-66-132 total strokes to tie Jack Grout and Henry Picard 67-65-132 in the Mid-South Pro – Pro Best Ball Golf Tourney. The four-ball event was held at Pinehurst #2 in Pinehurst, North Carolina.  The title attached to these historical images is “Tying Pain in Southern Golf Tourney.” Below, is a photo taken of my father and Henry Picard upon completion of their round on November 16, 1938.