|Portrayed by:||Patrick Cassidy|
In the late 1980s, Laura Lang separated from her husband Lewis, and Laura and Henry dated. During their time together, Laura conceived Lana, but shortly afterward, reconciled with Lewis and raised Lana as their own.
Henry is a lawyer and married to Jennifer Small; they have two children together, son Tyler Small and daughter Kaitlyn Small. He once lost a high-profile case against Lionel Luthor and his company, casting Henry's reputation down the drain, and causing him to have a long hatred of the Luthor family.
Henry with his daughter Lana.
When Lana was sixteen, she found a photograph of her mother and an unidentified man, and took it to Lex Luthor to analyze and trace. Knowing her parents had separated, she began to believe the man could be her biological father. When she discovered the man was Henry Small, Lana approached Henry with her theory and he was shocked. He told her that he already had a family and that she shouldn't bother him again. However, Lana wrote him a heartfelt apology letter, and Henry had a change of heart. He met Lana at the Talon (a coffe shop founded and managed by Lana) and told her that he did want to know the truth.
After DNA testing confirmed that Lana was his biological child, they attempted to forge a relationship. However, the matter drove a wedge between Henry and his wife. Jennifer told Lana that Henry often seemed enthusiastic about new things, but eventually lost interest.
Lana asked Henry to help her and Clark Kent stop LuthorCorp from developing and destroying the Kawatche Caves. However, shortly after, Jennifer Small decided to divorce Henry because throughout their marriage, Henry never committed to anything, not even their children, and she felt it was unfair that he was attempting so hard to have a relationship with Lana. Lana backed away because she did not want to be the cause of the dissolution of Henry's marriage, even though Henry was unaware of this. They regrettably parted ways and the two have not made contact since.