Charcot arthropathy is characterized by joint dislocations, pathologic fractures, and debilitating deformities. Syphilis was believed to be the most common cause of Charcot arthropathy a century back, but now, it is one of the rare causes which get missed in the routine evaluation. We present a rare case of syphilitic Charcot joint in a middle aged, paraplegic, wheel-chaired bound male, who presented with a history of recurrent painless joint swelling. He underwent multiple surgeries on the left elbow to deal with his soft tissues and bony infections along with multiple courses of systemic high end antibiotics including anti-tubercular drugs without much benefit. He was even planned for midarm amputation. Timely opinion of dermatologist and correct interpretation of serological tests clinched the diagnosis. This case highlights a high index of suspicion and correct interpretation of serological test of syphilis is essential to diagnose tertiary syphilis. Timely management with injection benzathine penicllin resulted in life time gratifying outcome.