|Portrayed by||Christopher Stanley|
|First appearance||My Old Kentucky Home|
Henry Francis is the Director of Public Relations and Research for Nelson Rockefeller, New York's governor. He meets Betty Draper at a party hosted by Roger and Jane Sterling. After Henry's political maneuvering helps Betty and other housewives thwart a development project, he tells Betty that he enjoys making her happy and kisses her.
Unhappy in her marriage, Betty secretly starts to write Henry letters. "I suppose I wonder too much where you are and what you're doing," she says in one. Soon after, Henry shows up at the Draper's house, saying, "I wanted to see you." Betty decides to host a Rockefeller fundraiser in order to hide the true purpose of Henry's visit from Don. When Henry doesn't attend the fundraiser, Betty drives to his office to demand an explanation. "You had to come to me," he contends. "You're married." The two kiss, but when he locks his door she breaks away from him: "It's tawdry," she announces before leaving.
After Betty discovers Don's true identity, Henry reinforces his desire to make her happy and asks her to marry him. The two meet with a lawyer, who suggests that Betty divorce Don in Nevada. Henry asks Betty not to request a financial settlement. "I don't want you owing him anything," he says.
Almost a year after Betty and Don's divorce, both he and his new wife were still living in Don's home, a house he still was paying for. Don requests that if they do not move out soon, he will need to start collecting rent. After Don leaves, Henry tells Betty that he agrees with Don and that it is time for Betty to start looking for a house, and is promptly rebuffed by Betty.
Glen Bishop tells Sally that Betty and Don will never get back together, but that Betty and Henry will decide to move soon. While the family is out of the house, Glen and a friend trash the house. Henry searches the house, to find the rest of the house trashed.
After Sally cuts her hair while under the supposed care of Don, Betty slaps her upon her return. Henry tries to tell Betty that young girls do these sorts of things, taking notice from his own time raising his now grown daughter, to which Betty calls him soft. After Sally is caught masturbating at a friends house, Henry suggests professional help. Betty admits to a shocked and speechless Henry that at one point she saw a psychiatrist.
Ralph Stuben, a a New York political operative for Congressman John Lindsay, joined Henry and Betty for dinner at a restaurant the same night that Don was having dinner with Bethany Van Nuys. Ralph and Betty joined Henry in walking over to extend courteous hellos to Don, and then went on their way to their own table. Once they walk away Don mentions to Bethany that Ralph is about to have a horrible dinner. Betty was aggravated at the mere sight of Don and spent most of the dinner glaring at Don, and drinking copiously, embarrassing Henry. Later, on the way home, he tells Betty that she carries too much anger towards Don, comparing the situation to that of him and his own ex-wife, saying "Hate's a strong word, Betty. I hate Nazis. I have an ex-wife. She bothers me. I don't like seeing her. I don't hate her...I'm an adult." They get into an argument, and he also wonders out-loud if he and Betty got married to quickly, which aggravates Betty, as she was six-months pregnant when they met. On his way to work, he rammed his car into boxes that Don was storing in the garage. He then called Don and told him to pick up the boxes the day before Gene's birthday. He picked up the boxes, which were on the curb, and saw Henry mowing the lawn. Henry was slightly shocked when he saw Don show up for Gene's party, though Betty comforted him, telling him that she had everything.
After a visit by agents investigating Don's background, Betty told Henry that she didn't want any secrets between them.
Henry was happy to finally hear that Betty was ready to move out of the house.