In the summer of 1929, Smith began courting Anne Ludlow Cannon, the granddaughter of industrialist
James William Cannon and an heiress of the
Cannon Mills textile fortune. He often flew to
Concord, North Carolina, in order to take her on rides in his plane. Anne's father, Joe F. Cannon, insisted that the couple be married. In the early morning of November 16, 1929, he had the couple and himself chauffeured to
York,
South Carolina, arriving around 2:00 a.m., to be married in a
shotgun wedding. The marriage quickly deteriorated; at the annual society
Christmas party at the Robert E. Lee Hotel in Winston-Salem, Smith and Anne got into a fight. Afterward, the pair returned to their apartments at the
Carolina Hotel to host a dinner, still incensed. In the presence of Smith's friends, the fight escalated to the point where Smith twice slapped Anne and sent her to bed. Afterwards, he sat at an open window and sullenly threw dinner plates at the
streetcar tracks nine stories below. In her 1980 interview, Smith's sister Nancy recalled: "I know he had a very bad temper. Really, when he got angry, he was really angry." By early 1930, despite Anne being pregnant, the pair had effectively
separated. In August 1930 she gave birth to a daughter,
Anne Cannon Forsyth, who was sent to live with her grandparents in
Blowing Rock, North Carolina. About a month into the marriage, Smith's friend
Dwight Deere Wiman, heir to the
John Deere tractor fortune, visited Winston-Salem. Wiman was the producer of a hit
Broadway musical,
The Little Show. In April 1930, Smith went to see Wiman's touring company of
The Little Show in
Baltimore and was dazzled by star
Libby Holman and her performance, including her signature song "
Moanin' Low". After being introduced, Smith followed up with flowers and notes. Holman would spend the summer of 1930 in
Florida with friends; Smith followed her down in his plane, becoming part of her entourage. She would later claim that "Smith asked me to marry him that first summer, almost right after he had met me...I said no, I didn't think I should marry him because he was so young. And, of course, he hadn't his divorce yet and was still married. I told him I thought he had better wait a while. Besides, I was in the theater and didn't think it was fair to marry while still in the theater. He first agreed to that, to wait five years. Then he came to see me and said, 'You go on in the theater, Libby. I need you now. I never had any love in my life and I want someone like you, and as soon as I get my divorce I want you to marry me. I have been alone all my life.'" Holman's friends disliked Smith's brooding attitude but tolerated him as he paid for visits to
nightclubs,
speakeasies and mixings with New York's elite. His constant presence led to
Clifton Webb calling him Holman's personal mascot: "Smitty, the traveling bear."
Libby Holman Holman had a variety of relationships with
both men and women during her lifetime, most prominently with
DuPont heiress
Louisa d'Andelot Carpenter. Although friendly and affectionate to Smith, who was eight years her junior, friends felt she treated him like an "amiable buffoon." Smith continued to follow Libby in his plane, behaving increasingly erratically: in summer of 1930, he rented a cottage nearby Carpenter's house, with whom Holman was staying. When the pair sailed to Europe, he had
private detectives find where they were staying in
Paris and appeared on their doorstep. After following her back to the U.S., the two quarreled often as Smith repeatedly implored Holman to quit her career to marry him. They would fight in front of Holman's friends at the
Harlem speakeasies they liked to frequent. After one particular row, Smith flew west and passed the remaining summer in
California and
Colorado, though still continued to call Holman regularly on the telephone. On one occasion he landed in
Denver, checked into the
Brown Palace Hotel, and called Holman's apartment drunk. Over the call, he told her that if she didn't promise to marry him, he would kill himself. Holman managed to talk him down, then took a taxi to Webb's house to furiously vent to his mother that she'd "put herself on the spot for that damn fool kid." Holman went on to star in the hit Broadway revue
''Three's a Crowd''. Smith joined her in New York as the show cycled through over 200 performances; he saw almost every performance, sitting in the front row. Although they began dating and were identified as a couple, they continued to fight and Smith continued to threaten suicide. In June 1931, Smith rented a home near Holman's residence in
Sands Point, New York. While they continued to see each other, tension arose as Holman continued her longtime relationship with Carpenter. On one occasion, Holman and Carpenter, along with Holman's sister Marion,
Tallulah Bankhead and Bankhead's sister Eugenie, left Smith behind and sailed the
Long Island Sound for a week on a
yacht belonging to Louisa's father. After their return Smith and Holman were able to spend time together, but continuously fought. At one point, after Smith allegedly came across Holman and Carpenter together, he angrily sped off in his
Rolls-Royce roadster, drove it off a four-foot
retaining wall and crashed into the ocean. Flight instructor Peter Bonelli later remembered an episode in which Smith expressed
suicidal inclination. Holman, but not Smith, had been invited to a party hosted by the actress
Beatrice Lillie; upon learning he was being excluded, Smith hurried to the nearby airfield. Bonelli found him readying his plane for takeoff in tears: "I thought he had had another fight with Libby - he was always upset after these - and tried to kid him out of his mood...He told me that Beatrice Lillie was trying to break up his affair with Libby, that she was throwing a party for Libby but failed to invite him, although she knew that he was staying at Libby's cottage." Then, "He hopped off without giving his motors more than a minute's warming up. He zoomed up off the ground crazily. I thought he was going to crash. His plane wobbled but he held her nose up, then, straight as a crow flies, he headed out into the ocean...He was gone for seven hours and when he returned he admitted that he had intended flying straight out until, gas exhausted, he would fall into the ocean. The least little mechanical trouble would have finished him." On the opposite side of the spectrum, Smith also showered Libby with affection: once, he flew a low-flying plane over the Sands Point house, dropping rose petals by hand along the cottage's private walk to the beach. During the investigation into Smith's death in 1932, Holman would claim that he was deathly afraid of being kidnapped for
ransom. She described incidents of
paranoia, such as Smith leaving a dummy on top of his bed while he himself slept under it; lurking around the house with a
pistol if he heard a strange noise; accidentally firing said pistol inside the cottage on one occasion; and, once, upon hearing people talking outside the house, jumping out the back window and running two miles for police. However, biographers
Patrick Reynolds and
Tom Shachtman doubt the veracity of these statements. Police reports describing any of these incidents were never filed; furthermore, Holman claimed he was petrified of kidnappers before the time that the
Lindbergh kidnapping had gripped the national public consciousness.
Divorce and remarriage On August 26, 1931, Smith had his Savoia-Marchetti plane hauled aboard the
Cunard liner and sailed to
Southampton, then flying to London, to begin his 1931 round-the-world flight. However, he contracted the
flu while staying in a London hotel. Newspapers quoted alleged despondent letters said to have been sent to Holman while he was horribly ill: "I have been sick. I don't know what's the matter, but I never felt more like dying in a long time." Another alleged letter dated to September cabled her: "Why return now? Meet you later — but suicide is preferable. This is the last cable. Love, Smith," and another of the alleged same day: "Darling Angel. I would gladly come home if you were not going on with the show. I'll gladly give up this trip or anything I have to devote all my time to you, if you would do the same for me. If I get to the point where I simply cannot stand it without you for another minute, well, there's the old
Mauser with a few cartridges in it. I guess I've had my inning. It's time another team went to bat." In their book
The Gilded Leaf, biographers Patrick Reynolds and Shachtman speculate that Reynolds' purported repeated references to suicide were a form of emotional manipulation to obtain affection from Holman. A
mastoid infection forced Smith to return to the U.S. for treatment. After a successful surgery, he flew Anne out to
Reno,
Nevada, known informally as the "Divorce Capital of the World." In 1927, the required residency for citizenship — and then a
divorce — had only been six months; in 1931 it was further reduced to only six weeks. A variety of "divorce ranches" were created to cater to the wealthy coming to seek "quickie" divorces. Anne stayed at the "Lazy Me" ranch owned by Cornelius Vanderbilt Jr. to put in her residency. In the
deposition of the divorce, she reported that Smith made her feel "terribly nervous and upset." Smith testified that they separated because: "She likes big parties and I like small parties." The divorce was finalized November 23, 1931. The terms of the separation included that Anne would receive $500,000 of the trust he would come into, with their infant daughter Anne receiving the same amount. In his 1932 diary, after Smith's death, Brackett wrote: "... Smith Reynolds, when he came to New York, evidently felt a
Theda Bara lure in her [Holman] and they were married. I am sorry to report that
Howard Dietz [Libby's friend] tells me that early in the acquaintance Libby said, "'If the Cannon girl got a million out of this, why shouldn't I get five million?'" Six days later, on November 29, 1931, Smith married Holman in the parlor of the
justice of the peace in
Monroe,
Michigan. There was no time for a honeymoon: the new Libby Reynolds left to go back on tour, and Smith took his 17,000-mile journey. Both agreed to meet in Hong Kong for an official honeymoon. After the trip was over, the couple returned to the U.S. and settled for the summer at the Reynolda House. ==Death==