Three jailed for Medway aggravated burglary

Three men have been jailed after admitting their involvement in a targeted aggravated burglary in Medway.

During the ordeal on the evening of Monday 12 January 2026, attempts were made to rip the rings from an elderly woman’s hand, and her husband was attacked with CS spray.

The woman had stepped outside of her home in Rochester to take the rubbish to the bins, when a masked man appeared and pulled her to the ground before dragging 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 had found her husband in another room and sprayed CS spray into his eyes.

The victim was beaten and forced into handing over the watch he was wearing.

A search was carried out at the property, and a selection of watches and jewellery was stolen.

Four minutes after their arrival, the burglars left, locking the couple, who were in their 70s, in their own home and stealing their mobile phones to prevent them calling for help.

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

An investigation by Kent Police uncovered that the ringleader of the group was Jesse Eastwood, who had been planning the burglary for months.

Through regular calls to a serving prisoner he knew, Eastwood would talk about the information he was gathering, including descriptions of the victims, the layout of the house, the watches he wanted to steal and even how he planned to carry it all out.

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

The second man involved in the burglary was Thomas O’Sullivan, of Yalding Hill, Maidstone, who had known the victims through the kindness they had previously shown him and had even been on holidays with them. While living together, O’Sullivan had provided Eastwood with the information needed to create the plan to steal from them.

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

At the beginning of February, all three were arrested and charged with aggravated burglary which they admitted when they appeared at Maidstone Crown Court.

Sentenced

On Monday 12 October, 34 year old Eastwood, of Perry Hall Road, Orpington, was sentenced to 7 years and 8 months.
O’Sullivan, 27, was sentenced to 2 years and 5 months. Christopher David, of Downham Way, Bromley, received 6 years and 9 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. ‘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.’