Battle of Chakan

The Battle of Chakan was fought between the Maratha Empire and the Mughal Empire in the year 1660. Shaista Khan was ordered by Aurangzeb to attack Shivaji per the Mughal-Adilshahi accord. Shaista Khan, with his better equipped and provisioned army of 150,000 that was many times the size of the Maratha forces, seized Pune and the nearby fort of Chakan. At the time, Firangoji Narsala was the killedar (commander) of fort Chakan, which was defended by 300–350 Maratha soldiers. They were able to withstand the Mughal attack on the fort for one and a half month. The Mughal force was numbering over 21,000. Then, a burj (outer wall) was blown up with explosives. This created an opening to the fort allowing hordes of Mughals to breach the exterior portion of the fort. Firangoji, himself led the Maratha counterattack against a larger Mughal army. Eventually, the fort was lost with the capture of Firangoji, who then was brought before Shaista Khan, who, appreciating his bravery, offered him a jahagir (military commission) on the condition that he join the Mughal forces, which Firangoji declined. Admiring his loyalty, Shaista Khan pardoned Firangoji and set him free. Firangoji returned home and Shivaji awarded him a fort named Bhupalgad.

Shaista Khan pressed his advantage of larger, better provisioned and heavily armed Mughal army and made inroads into some of the Maratha territory. Although he held Pune for almost a year, he had little further success. He had set up his residence at Lal Mahal, Shivaji's palace, in the city of Pune.

Shaista Khan kept a tight security in Pune. However, Shivaji planned an attack on Shaista Khan amidst tight security. In April 1663, a wedding party had obtained special permission for a procession; Shivaji planned an attack using the wedding party as cover. The Marathas disguised themselves as the bridegroom's procession and entered Pune. Shivaji, having spent much of his youth in Pune, knew his way around the city and his own palace of Lal Mahal. Chimanaji Deshpande- one of the childhood friends of Shivaji aided him in this attack offering his services as a personal bodyguard. According to Babasaheb Purandare, since Mughal army also consisted of Maratha soldiers, it was difficult for someone to distinguish between Shivaji's Maratha soldiers and the Maratha soldiers of the Mughal army. Thus, taking advantage of this situation, Shivaji, along with a few of his trusted men, infiltrated the Mughal camp.

After overpowering and slaying of the palace guards, the Marathas broke into the mansion by breaching an outer wall. Chimnaji and Netaji Palkar entered first along with Babaji Deshpande, another of Shivaji's long time loyal associates, they approached Shaista Khan's quarters. Shivaji then personally confronted Shaista Khan in a face to face attack. Meanwhile, perceiving danger, one of Shaista's wives turned off the lights. Shivaji pursued Shaista Khan and severed three of his fingers with his sword (in the darkness) as he fled through an open window. Shaista Khan narrowly escaped death and lost his son and many of his guards and soldiers in the raid.

Within twenty-four hours of this attack, Shaista Khan left Pune and headed north towards Agra. An angered Aurangzeb transferred him to distant Bengal as a punishment for bringing embarrassment to the Mughals with his ignoble defeat in Pune.