Raffles is visited by old school chum Harry 'Bunny' Manders, who has fallen on hard times. Penniless himself, Raffles comes up with a scheme to pay off Bunny's gambling debt by getting the money from the most obvious source—a plot that launches the duo into a life of crime.

Visiting a reception at the Italian Ambassador's one evening, Raffles and Bunny conspire to steal an item of jewellery which is on display. But for the help of Faustina, a maid who works at the Embassy, they would have been caught. To repay her assistance, Raffles arranges to rescue her from the Embassy where she is being kept against her will by Count Corbucci, the evil Ambassador. All goes well, but there is a very nasty shock in wait for Raffles, and an endless night.

Kaiser Wilhelm of Germany is seeking to embarrass the British Government by using Herr Von Heumann, one of his agents, to hand back a priceless black pearl, which had once been a gift from Queen Victoria to her daughter, to the tribal leader from whence it originally came in the South Pacific, an area dominated by the British. Raffles is naturally infuriated at the behaviour of the Kaiser, but he is also very interested in acquiring the pearl for his own use. He wants to be able to spend the season playing the tables at Monte Carlo with Bunny with the proceeds of the sale of it. He feels very much put on the spot when he is approached by the British Government who want him to steal the pearl for them. This conflict of interests makes Raffles play his cards very close to his chest as he endeavours to successfully acquire the pearl for himself. Raffles and Bunny both end up joining the hunting set at a house party where Herr Von Heumann is also a guest.

Wandering the streets of London one night with Bunny, Raffles, who is becoming bored and blase about the ease with which he is able to steal from the rich, acts on the spur of the moment and breaks into a house while the owners are actually present. To his astonishment he finds that he has chosen the house of an old flame of his, a long lost love who is already married. He is discovered by this lady in the act of stealing her jewellery, but she confesses to Raffles that she still loves him, and wants him to go away with her. Raffles still loves the lady, but he also loves his life at The Albany, and playing cricket for England, and stealing diamonds. Raffles must find a way of maintaining the status quo.

Raffles and Bunny swipe the famous Royal Gold Cup from the British Museum, but a group of criminologists track them down, suspecting Raffles of the theft. The gentleman thief is forced to come up with an ingenious way to prove them wrong.

Brash and crude, Reuben Rosenthall is a real 'rough diamond': a self-made millionaire who wears his wealth in the most ostentatious way possible. In other words, he's an irresistible target for Raffles, if not for the more hesitant Bunny. But as the duo find out, Rosenthall has a trick or two up his own sleeve.

Bunny feels he needs to do more to justify his share of their ill-gotten gains, so the partners in crime plan a job in which he takes the lead. But when things don't quite go as expected—leaving the partners in a tight corner—Raffles has to take charge to get them out.

Raffles has his eye on the Van Den Berg's wedding presents, but finds that he has an engagement at Lord's to play cricket on the day that they go on display, so Bunny goes in his place. Bunny falls into the hands of Netje, the trigger-happy younger daughter of the Van Den Berg family who has taken it upon herself to guard the wedding presents from rogues and thieves.

Sir Arthur Rumbold, the pompous Secretary for Home Affairs, announces that he wishes to introduce much tougher penalties for offences against property. Raffles, believing this to be a step back into the dark ages of Botany Bay and transportation for life, is furious and determines to teach Sir Arthur a lesson by burgling his own substantial London home. Announcing to Bunny that the burglary will be an unplanned affair, Raffles goes enthusiastically to work, but it is not long before events start to go drastically wrong.

Loud mouthed Barney Maguire is America's champion heavy weight boxer. At Raffles' Club one evening he brags to Raffles and Bunny that he has a trap which would trap the cleverest of Cracksmen. He also insults the noble game of cricket and ridicules his English boxing opponent. This is enough to tempt Raffles into breaking and entering Maguire's premises, but he is unaware of the nature of the trap which awaits him. It is left to Bunny to save the day.

A friend of Raffles', Teddy Garland, finds that he is in debt to the vicious moneylender, Brigstock. Raffles and Bunny pay a visit to Brigstock and manage to pay Garland's debt back. Brigstock asks Raffles to steal a letter which is evidence in a court case pending against him. Raffles agrees, but has an agenda about which Brigstock knows nothing. Ultimately Raffles puts Brigstock into a position where he must choose between his love for his money and life itself.

Raffles tells Bunny that he is going off to Scotland to improve his Scots dialect. During his absence his rooms at The Albany will be renovated, and it becomes imperative that certain items are not found in Raffles' flat. Therefore, Bunny is entrusted with a chest full of silver, and Raffles requests that he lodge the chest of silver with the Bank. Bunny complies, but are things quite what they seem?

Somebody is setting himself up in opposition to Raffles as another gentleman thief, and Raffles doesn't like it, as he is being accused by Inspector Mackenzie of things which he did not do. Eventually Raffles pinpoints the thief as Lord Ernest Belville, and he and Bunny break into Belville's rooms in quest of some stolen loot. Eventually there is a confrontation between Raffles and Lord Ernest Belville, and things go very wrong indeed for one of them.