Milton Stubbs

"When my wife, Lena left me and took our boy, I fell apart."

Milton loves his job as Vice Principal at Newcrest High, but his affections don't end there, as he seems to have a thing for his boss, Claire Sullivan. Milton seems good-hearted, but little is known about him, apart from the fact that his wife, Lena took their only child and moved away.

Season 1
Milton enters Claire's office and tells her that her daughter, Stacey Sullivan has provided reporter Mary Munroe with private information about her and an article has been written, damaging Claire's reputation. The two go and read the article. Milton is with Claire when she is being questioned by the School Inspector about pupil Lola Blackwell's teenage pregnancy, and comforts her afterwards. He advises her to get go of Lola as it may impress the School Board. Claire refuses and tells the School Board she plans to keep Lola at Newcrest High. Milton accompanies Kara Belic and Noah Belic in Claire's office when their grandpa, Arthur Belic dies, and introduces them to Samuel, a social worker who has been called to take Kara to Willow Creek. He comforts Noah, who eventually lets Kara go.

Season 2
Milton talks to Claire before her wedding and suggests that Claire is rushing things with Frank Sullivan. He reveals his wife Lena took their son and left, which almost destroyed him. Claire ignores his advice and proceeds with the wedding. Milton looks unhappy when Claire and Frank marry at the alter. At the Wedding reception, Milton congratulates Claire, who calls him a good friend. Milton witnesses Claire's wedding go south as Frank's depravity is laid bare by their daughter, Katie Sullivan. Milton comforts Claire a lot, eventually confessing his attraction to her. He helps Claire visit Frank and order him to sign their divorce papers, and when Frank refuses, Milton is furious.