James "Jim" Bailey

A Saturday, April 6 visitation is scheduled from noon-4PM at Drake & Son Funeral Home, 5303 N. Western Ave. A service with full military honors will take place at 4PM. Flowers and contributions to the American Diabetes Association (ADA) are welcomed. Interment is private.

“At heart, Jim Bailey was a proud, tough ex-Marine, who was devoted to his family, and loved playing and coaching 16-inch Chicago-style softball,” said Monica Bailey, his wife. Bailey’s proudest coaching moment was helping Lane Tech High School’s 16-inch softball team, along with Hall-of-Fame coaches Tom Horn and Dave Ruhle, win the 2000 public league Chicago high school championship. After attending Roosevelt High School, Bailey followed the career path of his father and joined the U.S. Marines. He attended Radio Communications School, then served for three years as a Field Radio Operator at Camp Pendleton, CA. After boot camp, and earning a Rifle Marksman Badge, he returned to Chicago and married his first love, Erica Henger.

“Jim nearly died in a helicopter crash while on Marine maneuvers in California,” said Henger. “Later, as a passenger in a Jeep, he was involved in an accident on a sharp curve while returning from an operation in the field. He was thrown, the vehicle rolled, and crushed his right foot.” The doctor at the military base had to manually pop his broken bones back into place and told him he would probably not walk well, much less run and play softball again. Bailey was at a life crossroad in 1983. He vowed to show everyone he would walk and run again. “His doctor was amazed at his recovery. But he did not re-enlist, and was granted an honorable discharge,” Henger said. In 1984, Bailey started working at the U.S. Post Office in Skokie, a career that spanned more than 40 years. His last assignment was a service-vehicle trainer.

In 1991, Bailey met Monica Lawrence, his second wife. In 1994, they were married at Concordia Evangelical Lutheran Church in Chicago. The Bailey’s had two children, a son Joshua Ethan in 1997 (wife Hayley) and daughter Shannon Marie in 2002. “We had a crazy life together but his children were always the light of Jim’s life,” said Monica. “When our kids were small Jim played a lot of softball, so we would go to his games. Jim also helped raise his nephew T.J. and opened up his home to many of his family and friends.

He had such a big, caring heart. Bailey also coached football at the Neighborhood Boys and Girls Club on Irving Park Rd. and eventually Joshua’s football team there. He was a “sideline” coach to Joshua as he played football at Gordon Tech and to Shannon as she played basketball at Lane Tech.” Jim truly was a great coach and teacher in all fields of sports,” said Monica. “He was just a natural athlete and excelled at any sport. He loved to shoot pool and play poker.” Jim was also a diehard Cubs fan and went to many a game as his mother Joan worked at Wrigley in concession stands.

Over the past two years, Bailey encountered medical problems that resulted in the amputation of his right leg below the knee. Ironically, it was the same foot that was crushed in that 1983 Jeep accident. Unfortunately, diabetes took a toll on Bailey’s body and he succumbed to a heart attack on March 26th.

“Jim always was an unselfish man who put other people first,” said Bob Egan. A friend and veteran softball player who visited him in January after the amputation. “Jim was upbeat, working on learning to walk with his prosthetic. Bailey grew up in the North Center neighborhood near Bell Elementary School, where he played schoolyard 16-inch softball with future Hall-of-Fame pitcher Horn, and many others,” recalled Egan.

In 1980, Bailey joined “The Rox,” a fine young team, as the back-up pitcher to Tom Horn. In the early 1980’s, The Rox won championships at Clarendon, Hamlin, Revere and Welles parks. In 1983, the team finished fourth in the state tournament, and climbed into the final eight in the World Tournament. “Jim Bailey’s first wife’s family owned a weekend getaway from in Grass Lake, WI,” Egan recalled. “Several of The Rox players would stay there when we played in major softball tournaments in Trevor, WI. We socialized at Furlands Dugout, and had some great times. We were young, 16-inch players who loved the game.” Later, Bailey, a great organizer, launched his own “Under Age” softball team with a nucleus of talented, young former Lane Tech championship players. “Forming and coaching Under Age was one of Jim’s major softball accomplishments,” Egan said. “The team had much success, winning many games at Horner Park, and other North Side parks and in tournaments. Most of the players Jim coached moved on to the highest level of ‘AA’ 16-inch softball in the Mount Prospect Leagues,” Egan noted. Bailey also coached women’s teams. His first wife’s team was called “Bad Habit,” because of its losing record. The next season Bailey, who hated to lose, coached the women to a championship, and they renamed the team “Sure Thing.” Later, Bailey formed another team called “Shockers” with his second wife. “Jim will be missed by all who grew up and played with him he will always be remembered,” Egan said.

Jim is survived by his wife Monica; his son Joshua (Hayley), his daughter Shannon; loving Uncle, father figure to TJ (Elba) and Maggie, former husband to Erica; nephew to Barbara; loving cousin and loyal friend to many. He is preceded in death by his father, James Sr., mother Joan, and siblings Timothy and Donna. The family would like to acknowledge and thank his many health care practitioners, most especially: Dr. Alan (therapist), Dr. Flannigan (foot doctor), Paul (home healthcare nurse), and Max (physical therapist).