The Many Marriages of Sidney Reilly

Yet another Week of Weddings two-partner, this time looking at the many marriages of Sidney Reilly, just in time for Throwback Thursday.


Sam Neill as Sidney Reilly during his first wedding on Reilly: Ace of Spies.

Sam Neill as Sidney Reilly during his first wedding on Reilly: Ace of Spies (Episode: “An Affair with a Married Woman”).


Sam Neill as the former Shlomo Rosenblum, now Sidney Reilly, an ex-professor hired as an informant for the British Secret Service

Southampton, Summer 1901

Series: Reilly: Ace of Spies
Episode: “An Affair with a Married Woman” (Episode 1)
Air Date: September 5, 1983
Director: Jim Goddard
Costume Designer: Elizabeth Waller


Hopefully you know all about Reilly from the first Reilly: Ace of Spies post on this blog. What? You don’t want to go back and read all million paragraphs I wrote? Too bad, here’s a million more:

The first episode, “An Affair with a Married Woman”, quickly establishes Reilly as a cunning man who will stop at nothing in pursuit of his goals. In the summer of 1901, the young Reilly’s primary goal is money. Thus, the following sequence is appealing to him:

  1. Reilly meets a young woman who is married to a rich older man
  2. Reilly sleeps with the young woman, who falls in love with him
  3. The rich older man dies, leaving the young woman with a lot of money

In the series, Reilly meets the woman, namely Margaret Callaghan, while she is traveling with her elderly husband, Rev. Hugh Thomas, through Baku in the late months of 1900. Reilly is on a mission and is suspected to have compromising documents. He uses his affair with Margaret to escape. Six months later, all parties are back in London. After a tempestuous reuniting, Margaret falls for Reilly. She begins ignoring her increasingly sick husband. Come May, the man is dead. Reilly arrives at the house and sees a casket. Margaret raises a bottle of champagne, two glasses, and smiles: “He’s dead!” We next see the happy couple on ship, tying the knot.

Interesting, right? Here’s what really happened:

Suspected of murder, young Rosenblum (named either Georgi, Shlomo, Solomon, or Sigmund!) arrived in London from Paris. While in London, he established the Ozone Preparations Company, using his chemistry background to sell “miracle cures”. In late 1897, the elderly Reverend Thomas came to him in need with a kidney inflammation. Thomas had two things Reilly wanted: a hot young wife and a substantial amount of money. Reilly made the steps to obtain both, first by engaging in a torrid six-month affair with Margaret. Next, Reverend Thomas altered his will, naming Margaret as its executor on March 4, 1898.

A week later, Thomas and his nurse showed up at the London and Paris Hotel, where Thomas died overnight. He was examined by Dr. T.W. Andrew, who quickly determined the cause of death as generic influenza and left, signing papers stating there was no need for an inquest. After the passing of 36 hours, Reverend Thomas was buried at the insistence of his grieving young wife Margaret, who inherited £800,000 six weeks later. Although not considered “appropriate” grieving time in late Victorian London, Margaret married Sigmund Rosenblum/Sidney Reilly on August 22, 1898.

Reilly eventually moved on past Margaret, with at least two or three additional marriages and countless affairs, but he now had money, a bed companion, and the means to a new identity, that of Special Branch operative Sidney George Reilly.

Who was Dr. T.W. Andrew? Odd that no record can be found of him in London or anywhere in England at the time. Contemporary descriptions reveal a young man, possibly under 30, with Jewish features. Naturally, this man was Reilly. In an interesting turn, Reilly was in Paris in 1908 when Louisa Lewis, the daughter of the proprietor of the hotel where Thomas died, recognized Dr. Andrew at a Paris hotel. She was never seen again.

What’d He Wear?

We only see the top half of Reilly’s wedding attire, but it is a fine example of Edwardian wedding wear.

"Why, you damnable rogue!" - someone who probably would've called him this back then

Why, you damnable rogue!

Reilly wears a rich brown wool frock coat, which were on the verge of extinction as cutaway coats and lounge suits were taking over. Brown frock coats remained in style for grooms until around 1914, when more world innocence was lost in the Great War and practicality began dictating fashion. Reilly’s coat is wool with satin-faced peak lapels and a double-breasted opening, however it is worn correctly when unbuttoned. On the Edwardian-style cuffs are three small uncovered buttons. Given the celebration, Reilly wears a white carnation on his left coat lapel.

The waistcoat underneath is a dark chocolate brown double-breasted vest with peak lapels and welted hip pockets. It covers much of his shirt, which is white with a detachable standing collar and French cuffs. The cuffs are fastened with large round silver links. Through the shirt, Reilly wears a dark brown silk cravat with tan polka dots throughout. The cravat is held in place by a pearl stickpin.

Reilly wears his gold pocket watch strung through the waistcoat buttonholes, worn “double Albert” style in his vest’s welted left pocket.

Ace of Spies indeed.

Ace of Spies indeed.

What pants would go with attire such as this? The standard black and white sponge bag trousers would likely contrast too much with Reilly’s brown tones, so the pants probably feature a brown pattern: either stripes, a shepherd’s check, or a Prince of Wales check.

How to Get the Look

Reilly gives us the top half of his attire but leaves the bottom half to our imagination. Either that or he’s just very ready to consummate his marriage.

  • Brown frock coat with satin-faced peak lapels and 3-button cuffs
  • Dark brown double-breasted waistcoat with peak lapels and welted pockets
  • Brown patterned flat front “sponge bag” trousers
  • White shirt with detachable standing collar and double/French cuffs
  • Dark brown (w/ tan polka dots) silk cravat
  • Pearl stickpin
  • Gold pocket watch on gold chain, worn “double Albert” style across waistcoat
  • Large round silver cuff links
  • White carnation, worn on left coat lapel


Sam Neill as Sidney Reilly on his final wedding day in Reilly: Ace of Spies (Episode: "The Last Journey")

Sam Neill as Sidney Reilly on his final wedding day in Reilly: Ace of Spies (Episode: “The Last Journey”).


Sam Neill as Sidney Reilly, world-weary ex-British agent now raising money for anti-Bolshevik terrorist groups

London, summer 1925

Series: Reilly: Ace of Spies
Episode: “The Last Journey” (Episode 11)
Air Date: November 9, 1983
Director: Jim Goddard
Costume Designer: Elizabeth Waller


By the time of “The Last Journey” in summer 1925, Reilly is tired from his quarter century of service to the British Secret Service and has been spending the last seven years raising money for groups such as Boris Savinkov’s splinter group and The Trust, an OGPU organization designed to lure in anti-Bolsheviks such as Reilly.

The previous year, Reilly met actress Pepita Bobadilla (real name Nellie Burton) in a Berlin hotel. Despite a large age difference, the two were married the next year in London.

Slightly adapted for fiction, the real story found Pepita with her mother and sister at the Hotel Adlon in Berlin (where Michael Jackson infamously dangled his son over his room’s balcony) in December 1922. Soon, Pepita spied Reilly across the room, staring at her. Reilly got a member of the British delegation to introduce them and they became secretly engaged by the end of the week.

They were married on May 18, 1923 at the St. Martin Register Office in Covent Garden, with Captain George Hill, Pepita’s sister Alice, and Stephen Alley – an MI6/SIS officer – standing in as witnesses. Following the ceremony, the wedding party was joined by fellow Secret Service acquaintances and theater friends of Pepita’s.

Nellie Burton, aka Pepita Bobadilla, Reilly's last wife, in London, 1919.

Nellie Burton, aka Pepita Bobadilla, Reilly’s last wife, in London, 1919.

Pepita was likely the most fetching of Reilly’s wives; I haven’t seen photos of the others but – as they were married for convenience rather than lust – it’s probable that the actress was the best-looking of the bunch.

Here she is naked! (sort of)

It was also Pepita that showed the most true devotion to Reilly; Margaret, long abandoned, now only seemed to want money from him and the Secret Service and Nadia was equally prone to philandering. Reilly is known to have had at least six mistresses during his five year marriage to Nadia. However, with Pepita, he broke off a three year relationship with 21-year-old art student Caryll Houselander as soon as he became engaged. If Reilly had ever in his life altruistically married for love, Pepita was it.

What’d He Wear?

Again, Reilly’s wedding is only briefly seen, so a few things are left up to convention or guesswork to decide.

The look is a 1920s take on the “black lounge” alternative favored by James Bond in On Her Majesty’s Secret Service, with a proper black lounge coat. The coat has the appropriate peak lapels and 1-button cuffs, closing in the front with a single button. Naturally, there is a white carnation on his left lapel. Underneath the coat is a dove gray 6-button vest with no lapels or watchchain. Although he is wearing a lounge coat instead of a cutaway coat and is thus less formal, Reilly keeps all six buttons fastened rather than unbuttoning the bottom one for comfort.

Despite the presence of his wife, Reilly still thinks it's cool to be a dick to a Bolshevik who just wants to congratulate him.

Despite the presence of his wife, Reilly still thinks it’s cool to be a dick to a Bolshevik who just wants to congratulate him.

This time, Reilly’s pants are visible, a pair of gray flat front trousers with thin black stripes, as appropriate with this type of attire. Unfortunately, we don’t see his shoes but they are likely a pair of black leather oxfords or balmorals with black socks.

The shirt is white with a detachable wing collar, French cuffs, and gold collar pins in the front and back to fasten the collar into place. His gray necktie has thin right-down-to-left American-style stripes and is tied in a four-in-hand knot.

Reilly confers with Hill, his co-worker, best friend, and witness to his wedding.

Reilly confers with Hill, his co-worker, best friend, and witness to his wedding.

How to Get the Look

Reilly’s particular morning dress style was very appropriate for a 1920s wedding.

  • Black single-breasted 1-button lounge coat with peak lapels and 1-button cuffs
  • Dove gray 6-button vest with no lapels
  • Gray flat front trousers with thin black stripes
  • White formal shirt with detachable wing collar (with gold pins) and double/French cuffs
  • Gray four-in-hand necktie with thin white stripes (right-down-to-left)
  • White carnation, worn on left coat lapel
  • Black leather oxfords/balmorals
  • Black dress socks

Go Big or Go Home – Wedding Edition

The Venues

Perhaps since neither of Reilly’s marriages were out of love, the venues were small and practical. The first wedding, in summer of 1901, is seen with the reception on board a ship bound for East Asia, where Reilly and new wife Margaret will be making their life in Manchuria as Reilly spies on oil deposits and fleet movements. Romantic.

Later, in the middle of 1925, Reilly has nothing on his mind but counter-revolution. No time for a large church ceremony, especially since Reilly is secretly a Jew, so he and Pepita are married in a small civil ceremony without even time for celebratory cigars and champagne…

(The actual May 1923 wedding took place at the Registrar Office on Henrietta Street in Covent Garden, followed by a grand reception at the Savoy Hotel. Evidently, the real life Reilly had a little more time to celebrate.)

The Refreshments

… Hey, speaking of cigars and champagne, guess what Reilly had at his 1901 reception? Cigars and champagne. Probably Moët & Chandon, which featured on the show plenty and also happens to be delicious.

Notable Guests and Gifts

Since his marriages were for convenience and money, it would make sense that Reilly’s boss attend both. On the show, the jolly Cummings (played by the excellent Norman Rodway) is there to give Reilly a proper send-off both times. In real life, this would have been Captain Mansfield Smith-Cumming, aka “C”, the head of the British Secret Service since its inception in 1909. Cumming was likely not present at either wedding. In 1898, Cumming was still eleven years away from his MI6 career and almost twenty years away from actually meeting Reilly. By the time of Reilly’s final wedding, in 1923, Cumming was less than a month away from death and – in real life – quite angry with Reilly for the way he had abused his commission in MI6 and lied about his RFC title on several occasions.

An interesting look at the back of the jacket but doesn't Norman Rodway look just delighted to be in this scene?!

Doesn’t Norman Rodway look just delighted

to be in this scene?!However, there definitely was a government presence at the weddings. At Reilly’s first wedding on August 22, 1898 (1901 in the show), the two witnesses at the ceremony were Admiralty clerk Joseph Bell and government official Charles Richard Cross. Both Bell and Cross eventually married the daughters of Henry Freeman Pannett, one of William Melville’s associates. William Melville was Reilly’s first British Secret Service mentor, a role replaced by Cumming in the show’s early episodes. In real life, Melville abruptly quit Special Branch – of which he was superintendent – and directed the first British Secret Service organization, MO3, from his flat in London. He was the man behind the transformation of Sigmund Rosenblum into Sidney Reilly.

For his second wedding, set in the middle of 1925 in the series’ timeline, Reilly is among friends, including Captain George Hill – his fellow agent from Russia – and of course, Cummings. Many others are present, including an ex-Bolshevik who introduces himself to Reilly and is refused a handshake. It turns out that The Trust followed Reilly to his wedding, imploring him to help their cause. This would be the last happy moment of Reilly’s life, as The Trust turns out to be a false organization, created by Felix Dzerzhinsky for the express purpose of capturing anti-Bolsheviks like Reilly.

The Trust presents Reilly with the poster condemning him to death if he ever steps foot on Russian soil. Simultaneously the coolest and the shittiest wedding gift ever.

The Trust presents Reilly with the poster condemning him to death if he ever steps foot on Russian soil. Simultaneously the coolest and the shittiest wedding gift ever.

Sadly, Reilly’s ex-mistress, a plain artist named Caryll Houselander, is also present for the ceremony and is forced to run out, crying. In one of the show’s stranger moments, Hill runs outside and comforts her with a hug as he looks off into the skies as the show’s theme plays.

The real life wedding, on May 18, 1923, actually did find Captain George Hill serving as witness, as he does in the show. No word on whether or not Caryll was there, but it is doubtful.

Do Yourself a Favor and…

Buy the series.

Reilly is shown getting married in the first episode (“An Affair with a Married Woman”) and the penultimate eleventh episode (“The Last Journey”).

He also marries Nadia Massino in 1910, presumably around the time the sixth episode (“Dreadnoughts and Doublecrosses”) comes to a close.

The Quote

At his 1901 wedding, the former Rosenblum reveals his idea for a new name to Cummings, his boss.

Cummings: I’m not sure about this name Reilly – it’s Irish!
Reilly: Exactly. You see, the Irish are welcome in every country in the world, except this one.

Interestingly, Norman Rodway – who played Cummings – was Irish.

Doubly interesting, the man that Reilly would’ve been having this conversation with in real life would’ve been William Melville, an Irishman whose first wife’s surname was Reilly.


  1. Pingback: Sidney Reilly’s Edwardian Gray Suit | BAMF Style
  2. Pingback: 10 Shocking Crimes Of The Real James Bond – Go Viral Now
  3. Pingback: Sidney Reilly’s Corduroy Suit in Manchuria | BAMF Style
  4. Pingback: Sidney Reilly’s 1920s Black Lounge | BAMF Style
  5. proxy free list

    Hello,I read your blog named “The Many Marriages of Sidney Reilly | BAMF Style” on a regular basis.Your writing style is awesome, keep doing what you’re doing! And you can look our website about proxy free list.

  6. Pingback: 10 Unbelievable Crimes Of The Real James Bond - Factboyz - Top 10 Facts
  7. Morgan

    Bravo! Please do some more articles on the Ace of Spies fantastic wardrobe. They were a treat to see every single episode of this great series.

Leave a Reply