Jack Penn was born in Bloomington, the son of Clement and Mary Penn. His first occupation was with the Boyce Dray Line, a hauling company in Bloomington, (27 June 1927) and then with JF Humphreys, grocery wholesalers. It was in 1901, at the age of 36, he became a patrolman with the Bloomington Police Force. In all of these occupations, he worked with his long time friend, William Young.
The first time that Penn's name appeared the Pantagraph in connection with an arrest was on September 9, 1902. He was a patrolman responding to a call of shots fired in the Union Saloon at the corner of Main and Grove. Tom Purcell had been shot by "Big Dick" Reynolds and was treated at the police station. Penn and Patrolman Luckinbill were sent to look for Reynolds, who apparently was not difficult to find. He was located near the Union depot and arrested there. In reading the police reports, a definite pattern of arrests near the Union depot emerges, probably because this was one of the few ways for a suspect to leave town.
He quickly rose through the ranks and became a plainclothes detective, where he was quite successful in his work. The Pantagraph admired his detecting skills when he was able to find a stolen bicycle with very few clues. (20 Apr 1911) the number of arrests for individual officers were sometimes printed in the paper and in September of 1920 Jack Penn was the leader in arrests, with 13 arrests. (8 Oct 1920) One of those arrests was pharmacist William Krebs, who was selling Jamaica ginger -- a patent medicine popular during prohibition. (8 Sep 1920)
Some police work was extremely dramatic. On June 7, 1909 Charles Agle of 1101 E Jefferson Street called to report a suspicious person in his backyard. Penn went to the scene with Sergeant Boyce, and upon establishing that there was more than one suspect, they called William Young in and deputized a young man at the Agle home to help them. All four men were armed as they chased down the suspects. Three men were routed by the officers (and volunteer) and the chase continued for an hour. They chased through yards and alleys, firing off their guns in an attempt to bring down the suspects. However, since it was dark "they did not aim to kill" in case they hit one of their partners. The chase ended at Heafer's brick yard, without any arrests being made. (8 Jun 1909)
Jack Penn's sometime partner, William Young, was quite the prankster. The Pantagraph reported about his jokes in the station house. In 1918 Young decided that alarming his fellow officers by pretending to be a drunk wagon driver would be amusing. He had seized a wagon during an arrest and tipped off one officer of his intentions, asking him to warn the beat officer that a drunk was driving a wagon in his direction. He was rewarded with a chewing out by the officer who managed to stop his erratic course.
Jack Penn was died of injuries sustained in a pedestrian vs auto accident at age 65. His wife Minnie Scannel survived him, along with their eight children. His funeral involved a procession from his home at 907 East Chestnut to Holy Trinity Church. The procession involved 16 uniformed officers, the entire city council, 3 Bloomington motorcycle policemen and three Illinois State motorcycle police. Graveside services were at St. Mary's cemetery.