May Carleton is a horse trainer and rich widow, who is enlisted by Thomas Shelby to train his horse for Epsom. She also enjoys the company of bad boys.
Background
May Carleton comes from a well-to-do family. She is well connected with everyone from the war-office to racing-board. Since her husband’s death, she has lived alone in her late husband’s mansion. Though she's a rich widow and a successful race-horse trainer, she is lonely and bored with her strait-laced life.
Series 2
May Carleton is at the horse auctions with her father, when Thomas Shelby and his gang arrive. Her interest is piqued by the bad boy Thomas, and she bids on the race-horse he's trying to buy to gain his attention. Afterwards, she offers to train Thomas's new horse.
Thomas eventually does hire May to train his new horse, who he names Grace’s Secret, believe it or not. When she comes to collect the horse, he asks May, point blank, if she wants to fuck him. "The horse is why I’m here," she tells him rather unconvincingly.
Thomas invites himself over to May's mansion to see just how the other half live and get a progress report on his horse. She reveals that she has lived alone since her husband’s death, and allows herself to be seduced by Thomas.
Later, Thomas visits May to confess that he still loves Grace and that they should break-up. But May is made of sterner stuff, and tells him: 'You’ve told me about her like a gentleman – now kindly behave like a gangster for me again,' she said, before adding: 'I will win you.'
At Epsom, Thomas bids a cryptic goodbye to May as she prepares his horse for the Derby, where the Peaky Blinders plan to hold up their rival Darby Sabini’s bookmakers and burn their licenses. May has influence with the Board, and can make sure that all the applications for legal pitches from Sabini's men at the Derby will be denied and instead allocated to Thomas's bookies.
After the race, May and Grace both wait for Thomas to turn up in the bar and find them, but instead find each other. They competed for his affections, they have a contempt exchange of words. May can ensure that the bookie’s licences go with the Peaky Blinders, while Grace fires a parting shot about the horse’s name.
At the end, Thomas announces that he's planning on getting married. The cliffhanger stands at it either being Grace, who is carrying his baby, or May, who carries the connections that will satisfy his business ambitions.
Quotes
Grace: "There's business and there's love."
May: "Is there? With Thomas Shelby?"
Grace: "What do you want?"
May: "Same as you. I want to feel alive."
"I'm May Carleton. I train Thomas Shelby's horse. And you're the woman he said would sail away." — May during her first encounter with Grace Burgess