John Joseph Montgomery began serious work in aeronautics in 1881-82. In the summer of 1884, he flew a monoplane glider between 100-200 m (325-650 ft) at Otay Mesa, California. In the late 1890s, early twentieth century, he experimented with tandem-wing gliders suspended beneath a balloon, which were then released to glide back to the ground.

The great San Francisco earthquake of 1906 ended Montgomery's aeronautical work for several years, but he resumed his efforts in 1911 with a new monoplane glider called the Evergreen. Between October 17-31, 1911, in the Evergreen Valley, just south of San Jose, Montgomery made more than 50 glides with his new aircraft, each approximately 240 m (785 ft). On October 31, flying at an altitude of less than 6 m (20 ft), the Evergreen stalled, sideslipped, came down on the right wingtip, and turn over. Montgomery hit his head on an exposed bolt and died from his injury two hours later.

John Joseph Montgomery was one of the earliest aeronautical experimenters in the United States. Born in 1858, he exhibited a boyhood interest in flight, making several aircraft models. He began serious work in aeronautics in 1881-82, developing models with flat wing surfaces. After these proved unsatisfactory, he patterned the lifting surfaces of his models after the curved wings of birds. In the 1884-1886, he built three full-sized gliders. The most significant was a monoplane glider spanning slightly more than 6 m (20 ft), and with it he made a glide between 100-200 m (325-650 ft) at Otay Mesa, California, in the summer of 1884. The glider had little means of control and was not flown again. At this time, Montgomery was working in isolation. Whatever merits his 1884 glider had, they were not disseminated among the aeronautical community until 1894, when Octave Chanute mentioned it in his compendium of flight research up to that time, Progress in Flying Machines. But even that account was very brief.

In the late 1890s and the first years of the twentieth century, Montgomery began experimenting with tandem-wing gliders. The first ones were small, unpiloted craft, typically flown tethered on a line between posts. Between 1904 and 1906, he built 3, possibly 4, larger tandem-winged gliders intended to carry a pilot, spanning 6-7 m (20-24 ft). The first was built and tested in 1904, again tethered to posts, with Montgomery on board. A slightly larger version followed, which was carried aloft suspended beneath a balloon, and then released to glide back to the ground. Montgomery enlisted Daniel John Maloney, a balloonist and parachutist, as his pilot. In 1905, they gained great attention with this glider, named the Santa Clara, after a series of public demonstrations in the spring and summer of that year. Maloney made several impressive glides on March 16, 17, and 20 in Santa Cruz, California. Then, on April 29, they made their first major public demonstration of the Santa Clara. Before 1,500 people, at Santa Clara College, Maloney ascended to an altitude of 1,200 m (3,900 ft) suspended from the balloon. After cutting the suspension rope he descended safely to the ground, much to the amazement and delight of the crowd.

The next major demonstration was scheduled for May 21 at the Alameda Race Track in San Jose, California. To raise funds for further aeronautical research and experimentation, admission to the event was charged. As before, Maloney began his ascent in the Santa Clara by balloon, but on this occasion the suspension rope snapped at an altitude of 45-60 m (150-200 ft). He managed to reach the ground safely, but the spectators, expecting more, were disappointed and booed Montgomery and Maloney. A second attempt was made with a back-up glider, similar to the Santa Clara, called the California. Once aloft, problems arose with the balloon and the glider and, in the interest of safety, Maloney simply descended with balloon and glider still connected, landing 50 km (31 mi) away. The failures were humiliating after the triumph of April 29.

On July 18, 1905, Montgomery and Maloney were back at Santa Clara College for another attempt to fly the Santa Clara. Again a problem occurred, but this time Maloney was not so fortunate. As the balloon was released, one of its handling lines, unnoticed by Maloney, was caught up in the structure of the Santa Clara above the wings. Montgomery saw the mishap and called to his unsuspecting pilot to just ride down with the balloon. Maloney failed to hear him and ascended to 1,200 m (3,900 ft). After cutting the suspension rope as normal, the errant handling line damaged the glider. Maloney struggled unsuccessfully to gain control of the crippled craft and crashed to his death.

Undeterred by the mishap, Montgomery resumed his experiments late in 1905 and early 1906. He returned to the earlier method of flight testing his gliders tethered to posts arranged on a hillside. On February 22, 1906, however, another balloon ascension with a suspended glider was made, presumably with the repaired Santa Clara or the California, or possibly some other glider. The pilot, David Wilkie, lost control of the glider as it separated from the balloon at 600 m (2,000 ft), only regaining equilibrium at 90 m (300 ft) when he could hear Montgomery shouting instructions from the ground. The glider was slightly damaged upon landing. Wilkie convinced Montgomery to let him make a second try a few days later, but the balloon was damaged during inflation so no flight could be attempted. Montgomery then decided not to allow Wilkie another balloon-assisted flight trial.

The great San Francisco earthquake of 1906 ended Montgomery's aeronautical work for several years, but he resumed his efforts in 1911 with a new glider called the Evergreen. Moving away from his basic tandem-winged design of the pre-1906 period, the Evergreen was a monoplane glider with a conventional tail with the pilot seated below the wing. Montgomery flew the Evergreen himself. Between October 17-31, 1911, in the Evergreen Valley, just south of San Jose, he made more than 50 glides with his new aircraft, each approximately 240 m (785 ft). On October 31, after making an adjustment to the angle of the horizontal stabilizer, he was airborne once again. Flying at an altitude of less than 6 m (20 ft), the Evergreen stalled, sideslipped, came down on the right wingtip, and turn over. Montgomery hit his head on an exposed bolt and died from his injury two hours later.

After his death, the remains of Montgomery's gliders were given to the University of Santa Clara. In 1947, the Smithsonian Institution acquired from the university parts of the Evergreen and what was believed to be a wing panel from the Santa Clara. In 1979-80 the Evergreen was restored. At that time, the university sent some further original parts of the Evergreen that were not included in the original Smithsonian acquisition in 1947. This enabled the restored aircraft to be 80-85 percent original. The museum also has, from the 1947 acquisition, one wing panel from one of the tandem-winged Montgomery gliders of 1904-05. Initially believed to be from the Santa Clara, in which Maloney was killed in 1905, it is shorter in span, has many fewer ribs than the Santa Clara wing, and is therefore almost certainly from the slightly smaller, earlier tandem-winged first prototype. It is preserved in its original condition.