MacAndrew arrived in New York in 1899 to go to Chicopee Falls, Massachusetts, to supervise the manufacture of golf clubs for the Spalding Company.
During this time, Spalding became embroiled in a dispute with its former supplier, Overman Wheel Company, and business suffered.
[5] MacAndrew was subsequently offered a job by one of Spalding's competitors, Crawford, McGregor, and Canby, another of the early U.S. golf club makers.
MacAndrew began to develop a reputation, said 1930 Tennessean sportswriter Tony Scheffer, "as a teacher of note turning out some wonderful golfers under his diligent tutelage".
[3] A group of prominent citizens had aspirations of forming a golf-based country club with a golf course rivaling the quality of those in Scotland; they hired MacAndrew to design and build it.
[2] MacAndrew's four sons followed his career path to become professional golfers: James, Robert, John (Jock) and Charles.
He rode "Saggy", the horse that famously defeated the previously unbeaten Citation (ridden by Eddie Arcaro) in the Chesapeake Trial Stakes at Havre de Grace Racetrack on April 12, 1948.