Oscar Willing began playing golf at an early age. His family lived near Waverley Country Club in Portland and, as a youngster, he’d earn spare change by caddying at the club. He soon developed a flair for the game that would lead him to the top echelon of Northwest golf.

Willing played golf while in dental school in Montreal during World War I. Once Willing turned his attention to the tournament trail upon returning to Portland and joining Waverley in 1918, he became known for his long drives, crisp iron play, and phenomenal short game. Willing rapidly rose to national prominence, giving budding Oregon golfers a role model and helping establish Portland as one of America’s golfing hotbeds.

Oscar’s ascent in the golf world began when he captured the 1919 Oregon Coast Invitational at Gearhart. He followed that victory by winning the Portland City Amateurs held at Eastmoreland in 1920 and 1921. In 1921 Willing enjoyed the first of his many “big” years when he won the first of two consecutive state events and played in the U.S. Amateur in St. Louis, losing in the second round to a young Bobby Jones. Oscar went on to win five Oregon Amateur titles, the last in 1938, and was runner-up twice.

The 1924 PNGA Men’s Amateur Championship was held at Shaughnessy Heights Golf Club in Vancouver, B.C., where the Calcutta pools picked former British Amateur champion, Willie Hunter, and Vera Hutchings to win their respective events. Hunter certainly had outstanding credentials. He was the low amateur in the 1920 British Open, winner of the 1921 British Open, and semifinalist in the 1922 British Amateur. Hunter lost in the semifinals of the 1922 U.S. Amateur, and won the 1923 Southern California Amateur Championship. Chandler Egan, the only competitor from the Northwest who was said to be able to challenge Hunter, did not enter the 1924 PNGA.

“Doc” Willing and Hunter made it through the preliminary rounds. Then, before a crowd of 2,500 spectators, the Portland dentist defeated Hunter in one of the most sensational matches in PNGA history. Commented Hunter after his 2 & 1 defeat, “I have just received my greatest golfing lesson.” The match was a triumph in steadiness over brilliant shot-making. After nine holes, Willing was 5-down as Hunter was seemingly en route to a new course record. But Hunter began encountering difficulties at the 10th hole and, after the first 18, Willing was only 1-down. The good doctor grabbed the lead in the afternoon round and never relinquished it.

Another monumental year for Willing was 1928, when he won the second of his two PNGA Men’s Amateur titles, as well as the Oregon and Northwest Opens. The latter two events found him overcoming the best golf professionals on the West Coast.

All of the Northwest’s finest players gathered at Portland Golf Club for the 1928 PNGA Championship, the season’s major golfing event and what developed into the largest PNGA event to date. The old saying, “youth must be served,” was not true that year. After all the silverware was distributed, the top two trophies went to the “King and Queen of the Northwest Fairways,” Dr. Oscar Willing and Violet Pooley Sweeny.

Willing, by then a veteran campaigner and a member of the USGA’s Walker Cup team, played superbly from tee to green throughout 1928. In all the tournaments he entered, the Waverley member schooled his less experienced opponents. In the Northwest Open, he defeated Walter Pursey, then gave young Don Moe a golfing lesson in the PNGA Men’s Amateur final. Though shooting one-under-par in the opening 18 on the final day, Moe was still 3-down.

The only real opposition Willing had in 1928 was from fellow Portlander, Eddie Hogan, who entered his first PNGA event that year. Young Hogan and the doctor tied for medalist honors; Eddie was not asked to enter a playoff as Willing waived his claim by giving the youngster medalist honors.

The 1929 campaign found Willing a finalist in the U.S. Amateur at fabled Pebble Beach Golf Links, where he bowed to Harrison Johnston of Minnesota. In the quarterfinals, the dentist had defeated the famed long-hitting British Amateur champion, Cyril Tolley, 4 & 3. In the semifinals, Willing bested fellow clubmate Chandler Egan, 4 & 3.

In 1931 Willing continued his stellar play, reaching the semifinals of the Western Amateur at Portland Golf Club, which was won by another Rose City resident, Don Moe. Later, Willing joined the Northwest Seniors Golf Association, winning the group’s 1954 championship.

Willing was the first Northwest golfer named to the USGA’s prestigious Walker Cup team. First appointed in 1923, Willing was also on the 1924 and 1930 teams. During his tenure as a Walker Cup competitor, the steady-playing dentist won each of his matches. His late victory in 1923 in England decided the matches in favor of the Americans. During his time in England for the 1923 Walker Cup Matches, Willing played in the St. George’s Gold Vase tournament, Great Britain’s annual stroke-play classic for amateurs, where he tied for first with the incomparable Francis Ouimet.

Willing considered his narrow win in the 1928 Oregon Open at Waverley — when he nipped Johnny Farrell, the 1928 U.S. Open champion, by a single stroke — his greatest victory. Willing’s fondness for that win probably stems from what happened the previous year, when he lost in the Oregon Open, at that time a professional tour event.