Stranded at home the past couple of months with no trips for tournaments or travel features, I have reluctantly taken on a few projects, one of which has entailed cleaning out the garage. In doing so, I uncovered some long-forgotten gems: a box of clips from my first newspaper job, which I started at the Burlington Free Press the night in 1981 when Bernie Sanders was elected mayor of that Vermont city, a stack of Grateful Dead albums, and perhaps best of all, my last set of persimmon woods, which bore the signature of the man who designed them, Toney Penna.
The heads of those clubs are tiny, 190cc for my old driver versus 460cc for the titanium bomber in my bag today. And the tops are a luscious light brown, with thin, dark streaks of grain. As for the sweet spots, they feature a plastic called cycolac that is red in color and attached to the face with four screws. I admired the sheer artistry of the sticks and recalled the euphonious sounds they produced on those rare occasions when I made good contact.
As I considered the craftsmanship, I also reflected on the man who had designed the clubs and the mark he made in the game. As a fierce competitor with five professional victories in the 1930s and ’40s and a pair of top-10s in both the Masters and the U.S. Open. As a clubmaker and designer who held four patents and ran the tour program at MacGregor Golf for more than three decades. As the person who gave Bing Crosby the idea for the annual pro-am that came to be the Crosby Clambake, putting Penna’s friends from professional golf together with the crooner’s cronies from Hollywood. And as the founder in 1967 of the Toney Penna Golf Company, whose clubs were used by the likes of Tom Watson and Lee Trevino to win major championships.
Born in Naples, Italy, in 1908, the son of a carpenter, Penna emigrated to the States with his parents as well as his sister and two brothers when he was just 5 years old. After being processed on Ellis Island, the family moved to the town of Harrison, New York, in Westchester County some 30 miles northeast of Manhattan.
Penna’s introduction to golf came at age 11 when he started caddying at the Apawamis Club in the nearby town of Rye. It was not an easy one. Barely 5 feet tall at the time, Penna often found himself fighting with older and bigger loopers who were especially fond of hurling ethnic slurs at him. The beatings were tough, but Penna never backed down.
The work was no picnic either. His pay came to 35 cents for an 18-hole round. But in time he started developing an affection for golf. In addition to caddying, Penna learned how to swing a club and took an interest in clubmaking and repair as he watched the professionals at Apawamis tend to their members’ sticks. Soon, he became a favorite of the caddie master, a fellow named George Hughes.
According to his charming autobiography, My Wonderful World Of Golf, Penna started looping at the neighboring – and now defunct – Green Meadow Country Club when Hughes took a job there as a professional. Many of the Apawamis caddies also followed Hughes to his new place. Penna was delighted that his old boss asked him to work in the bag room on occasion.
“Tom Watson, Lee Trevino, Seve Ballesteros and Gary Player all won majors playing his clubs. And at one point, some 20 percent of the professionals on the PGA Tour had one or more Toney Penna woods in their bags.” – Nathaniel Crosby
Around then, Penna’s father told his son it was time to learn a trade. Penna asked if it was all right to work in the golf business, and the old man approved, so long as Toney was sure that was how he wanted to make a living.
Penna’s next gig was as a caddie at Westchester Country Club, where his first loop was Tommy Armour, the eventual winner of three major championships as well as the club’s golf secretary. In addition to becoming the Silver Scot’s regular caddie, Penna started working in the shop of Westchester head professional Alex Smith, the native of Carnoustie, Scotland, who had captured the 1906 and 1910 U.S. Opens. From those two gentlemen, Penna received what were effectively advanced degrees in the mechanics of the golf swing as well clubmaking and repair. Sometimes Smith organized games for Penna with members, imploring him to listen to how they spoke and to watch how they acted – and to learn from those interactions.
After two years at Westchester, Penna left when Armour became the head professional at Congressional Country Club near Washington D.C., and asked his old looper to be his assistant. Five years later, in 1925, Penna assumed the top job for the first time, at the city-owned Osceola Golf Club in Pensacola, Florida.
While in Florida, Penna developed into an accomplished teacher and a good enough player to compete on the PGA Tour. He continued to play the circuit even after he moved to Chicago, Illinois, to assume the head professional position at nearby Itasca Country Club.
One day, the president of the MacGregor Golf Company, Clarence Rickey, called on Penna in his new job. A friendship grew. Rickey eventually asked Penna to join the clubmaker as an “emissary,” for $500 a month. His mission was to travel the country on MacGregor’s behalf, playing in the dozen or so tournaments that made up the PGA Tour in those days while building relationships with fellow golfers who might become endorsers one day.

Rickey also wanted Penna to visit local club professionals at their places of business. The hope in both cases, of course, was to bolster MacGregor sales while also procuring feedback on how the company might improve its products.
Penna officially started with MacGregor in 1934. Soon after, he signed Ben Hogan, Jimmy Demaret, Byron Nelson and his old friend and mentor Armour to playing contracts. Louise Suggs and Babe Didrikson Zaharias as well.
Between tournaments, Penna often returned to the MacGregor plant to assist in the design of new clubs. Along the way, he managed to win a few tournaments, starting with the Pennsylvania Open and the Kansas City Open, in 1937 and 1938 respectively, and then the Richmond Open in 1946 and and the Atlanta Open in 1947.
Penna eventually became executive vice president of MacGregor and helped it become the No. 1 clubmaker in America, bigger than Spalding, bigger than Wilson. The endorsers he signed no doubt helped in that ascension, and so did the relationships he had nurtured with the club pros.
“Toney was a true innovator,” says Nathaniel Crosby, the youngest of Bing’s seven children and the 1981 U.S. Amateur champion as well as a longtime student of Penna’s. “He was always trying to make a better golf club. He was always looking for the next best thing. He was at the forefront of investment casting, with an iron called the TP Superblade. He used different inserts in the clubface.”
Penna also had flair. He introduced color in clubs, grips and shafts, even creating in 1976 a red-white-and-blue driver in honor of the American Bicentennial. Just 5 feet, 6 inches tall, he fancied tailored clothes and custom-made shoes. Penna drove big, powerful automobiles fast, one time making the trip from Miami, Florida, to San Francisco, California, in two days, outracing several state troopers along the way. He had what one writer described as “a piano-key smile” but also possessed a fierce temper. Penna had a sense of humor, too, naming one of his custom wood models the LFF, for “Let The (F—er) Fly.” And he didn’t seem to mind when his friend Perry Como started calling the toupee Penna came to wear in his later years, “the divot.”
Penna stayed at MacGregor for more than three decades, at which point he started the Toney Penna Golf Company. Crosby, Como and Bob Hope all backed the new venture, with Hope attending the factory opening, in Jupiter, Florida, in 1967. Business boomed.
“Tom Watson, Lee Trevino, Seve Ballesteros and Gary Player all won majors playing his clubs,” says Crosby. “And at one point, some 20 percent of the professionals on the PGA Tour had one or more Toney Penna woods in their bags.”
Nathaniel Crosby met Penna in 1977, just two weeks before Bing passed away, on a golf course in Spain. “Dad arranged for Toney to give me a lesson at the Burlingame Country Club, just south of San Francisco,” says Crosby, who was 15 at the time. “And in later years, as I started to build my thoughts around becoming a better player, I decided to go to the University of Miami, in part because Toney was based in Florida and I could work with him there.”

Crosby ended up working a lot with his friend. “He was a great teacher and good fun to be around,” says Crosby. “He knew where to put your golf swing, and he promoted a very athletic move.
“He also never charged me for a lesson,” Crosby added. “So, one time I gave him one of my father’s old watches, a Patek Philippe, as a way of saying thanks.”
Clearly, their sessions paid off, as Crosby won the U.S. Amateur at the Olympic Club, just a few miles away from where he took that first lesson with Penna, and then took low amateur honors at the 1982 U.S. Open on another California course with a close Crosby connection, Pebble Beach.
Later that decade, the relationship entered a different phase when Crosby led a group that purchased the Toney Penna Golf Company. Crosby was 26 years old when the deal closed, and Penna was 80. Crosby ran the company for a spell and while the business never came close to approaching its previous success, there was something wonderfully karmic about Penna hooking up again with a Crosby.
Seven years later, the old pro and clubmaker passed away.