Howard, a staunch Royalist, raised a mortgage on his estates and used the money to raise and equip a body of men to fight under his command on the side of King Charles I, during the civil war. He was a brave and ferocious fighter in the royalist cause and received many commendations for his bravery. However, when the roundhead army was victorious, he lost his estates and with no income to live on was forced to take to the highways.
While he made a living from those he robbed, the money seemed to be secondary to his need for revenge against those that had murdered his king and stolen all that he had owned. To that end he picked as his victims only those that he considered as his enemies, i.e. The Parliamentarians.
The Earl of Essex, a former Parliamentary Commander-in Chief, was one of those that he targeted early on in his new career and he took from the Earl £1200 despite the fact that the Earl had a least six retainers with him.
On another occasion, Howard heard on the grape vine that General Fairfax had been given a gift of a quantity of silver plate while in Newcastle-upon-Tyne and was sending the plate and a covering letter to his wife by means of a courier. This was too good an opportunity to miss, so he waylaid the courier; unfortunately the man fought back and in the resultant shootout was killed. Taking the plate and the letter Howard made his escape and after stashing the silver plate in a safe place, he then made his way to the Fairfax house, handed over the letter and presented himself to Lady Fairfax as the courier. When the Lady asked where the plate was, he explained that having heard that a gang of robbers were patrolling the road, he has thought it best to leave it with an honest innkeeper and with her permission he would collect and return with the plate in two days.
Whatever else he said, he seemed to have convinced Lady Fairfax of his sincerity, so much so that she offered him a bed for the night in the servant's quarters. Howard accepted the offer and later that night after tying and gagging the servants a gunpoint, it was said that he raped Lady Fairfax and her daughter, filled his pockets with valuables and exited via the front door.
Incensed at the violation of his womenfolk and his household, to say nothing of the lost of his property, General Fairfax offered a reward of £500 for the capture of Howard. The resultant heat generated by the reward, forced Howard to flee to Ireland where he stayed until the hue and cry died down.
On returning to England, Howard travelled to Chester, where he booked into an inn. Imagine his surprise when he found that the Lord Protector, Oliver Cromwell himself was staying there. Howard introduced himself to Cromwell as a fellow puritan and after spending the evening in amiable conversation, was invited by the Protector up to his room for prayers. Once in the room Howard tied up Cromwell and after helping himself to some valuables, couldn't resist the urge to tip the contents of the chamber pot over the Lord Protectors head.
Another time while continuing his vendetta against his chosen enemy Howard waylaid the Earl of Portsmouth and his manservant. After robbing the Earl and shooting his horse, he couldn't resist adding insult to injury. He did this by forcing the men onto the remaining horse and after tying then together back to back, sent them on their way with the manservant facing forward and the furious Earl facing the animal's rump.
Howard continued his personal war against the puritans, but overstepped the mark at Blackheath near London when he unwisely decided to take on six parliamentarian officers at the same time. Despite killing one and wounding two of the men, Howard was eventually overpowered by the other three. After his arrest he was taken the Maidstone jail to await execution. While there he was visited by none other than Oliver Cromwell himself, though there is no record of what passed between them. The visit however did nothing to prevent the 32 year old Howard being executed for murder and robbery in 1652.
escape and after stashing the silver plate in a safe place, he then made his way to the Fairfax house, handed over the letter and presented himself to Lady Fairfax as the courier. When the Lady asked where the plate was, he explained that having heard that a gang of robbers were patrolling the road, he has thought it best to leave it with an honest innkeeper and with her permission he would collect and return with the plate in two days. 
some valuables, couldn't resist the urge to tip the contents of the chamber pot over the Lord Protectors head.