Three men jailed over violent targeted burglary at elderly couple's home in Rochester

A woman was grabbed by a masked man outside her home

Author: Maria GreenwoodPublished 13th Oct 2026

Three men have been jailed after admitting their involvement in a targeted aggravated burglary at an elderly couple's home in Rochester, Medway.

Kent Police said attempts were made to rip the rings from the woman's hand and her husband was attacked with CS spray during the burglary on the evening of Monday 12th January 2026.

The three men are ringleader Jesse Eastwood, Thomas O'Sullivan and Christopher David.

How the burglary unfolded

The woman had stepped outside her home to take the rubbish to the bins when a masked man appeared.

He pulled her to the ground and dragged her into the house.

He was followed by other intruders, all dressed in dark clothing.

As the man unsuccessfully tried to remove the rings from her fingers, one of the other attackers found her husband in another room and sprayed CS spray into his eyes.

The husband was beaten and forced to hand over the watch he was wearing.

The house was searched and a selection of watches and jewellery was stolen.

Four minutes after arriving, the burglars left.

They locked the couple, who were in their 70s, inside their own home and took their mobile phones to stop them calling for help.

The offenders left in a stolen car on false plates, which was found by police the following day.

How police identified the men

A Kent Police investigation found the ringleader was Jesse Eastwood, who had been planning the burglary for months.

Through regular calls to a serving prisoner he knew, Eastwood talked about the information he was gathering.

This included descriptions of the victims, the layout of the house, the watches he wanted to steal and how he planned to carry it all out.

After the burglary, he reported back about the experience and how the victims had been assaulted, likening it to a "horror story".

The second man involved was Thomas O'Sullivan, of Yalding Hill, Maidstone.

He had known the victims through the kindness they had previously shown him, and had even been on holidays with them.

O'Sullivan provided Eastwood with the information needed to create the plan to steal from the couple.

Forensic testing on a jewellery box belonging to the victims revealed the third offender to be 41-year-old Christopher David.

Charges and sentences

At the beginning of February, all three men were arrested and charged with aggravated burglary.

They admitted the offence when they appeared at Maidstone Crown Court.

On Monday 12th October, 34-year-old Eastwood, of Perry Hall Road, Orpington, was sentenced to seven years and eight months.

David, of Downham Way, Bromley, received six years and nine months.

The 27-year-old O'Sullivan was sentenced to two years and five months.

Detective Aaron Chapman said: "Eastwood spent nearly a year planning this burglary and recruiting others to assist him, yet officers worked quickly to uncover his identity and within weeks he had been charged along with his co-offenders."

He added: "The victims have remained courageous and steadfast throughout the investigation despite what they were forced to go through at the hands of their attackers. We thank them for their support of the case and hope the result will bring them peace and reassurance."

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