In 2001, Richard approached Juliet Burke in Miami. This meek fertility doctor was still under the watchful eye of her ex-husband, Edmund, as she conducted experiments in the hopes of impregnating her barren sister, Rachel. Ben sent Richard to recruit Juliet in the name of Mittelos Bioscience in his attempts to find the reason and cure for pregnant woman dying on the island. Alpert's assistant referred to him as "Dr. Alpert;" however. Juliet addressed him as "Mr. Alpert," suggesting that he might hold a Ph.D. but not be a doctor of medicine. Juliet declined after a cheerful slideshow about the Mittelos facility, supposedly located just outside Portland. She then joked bitterly that the only way she would be able to unisciti Mittelos was if Edmund were hit da a bus.
Later, Juliet discovered that her experiments had been successful, but as she told Edmund about it, he stepped off the curb and was hit da a bus bearing an Apollo Bar advertisement. After Juliet identified Edmund’s body, she was once again approached da Richard in the morgue, this time accompanied da Ethan. She was stunned as she remembered her dark joke to Richard, though he denied even remembering the comment. He once again offered Juliet a six-month job at Mittelos, carefully telling her that the facility wasn’t “quite in Portland.” ("Not in Portland")

Later, as Juliet and Rachel detto goodbye to each other at Herarat (an anagram reference to Amelia Earhart) Aviation, Richard and Ethan came down to greet them, telling them that unfortunately, they had to say goodbye at the gate. After Juliet signed the appropriate paperwork, Richard added powder to a glass of arancia, arancio succo, succo di frutta for her. When she asked warily about it, he was very forthcoming about it being a strong sedative for the "intense" journey. After Juliet drank the contents of the glass, Alpert presumably traveled to the Island on the Galaga with Ethan and Juliet. ("One of Us")