Longtime Woodstock attorney, William Caldwell, dies at 77

Ever the champion of fresh starts, longtime Woodstock attorney William “Bill” Caldwell encouraged his children to start each day with a deep breath of fresh air.

“ ‘Take in a big breath. Fill in your lungs with air,’ ” Caldwell’s daughter, Laura Caldwell said, quoting her father. “He wouldn’t let you in the car until you took in a couple lungs full of air.”

A longtime Woodstock attorney and lover of the outdoors, William “Bill” Caldwell, 77, died Monday in Surprise, Arizona, where he was visiting family during the winter months.

Caldwell was the father to four children, Laura Caldwell, 52, Katie Caldwell Kuhn, 50, Matt Caldwell, 47, and Christi Smith, 43. Funeral arrangements were pending as of Tuesday evening.

Caldwell, a Loyola University graduate, earned his law license in 1967 and went on to work at his father’s law practice in Woodstock. The firm later served as the backdrop to the recurring conversations between Bill Murray and Stephen Tobolowsky in the 1993 film “Groundhog Day.”

“Every time Needlenose Ned steps out, you can see Caldwell Berner and Caldwell swinging there,” Laura Caldwell said.

The law office at 100 Cass St. in the Woodstock Square is somewhat of a family landmark. For Bill Caldwell’s father, William Caldwell Sr., the business represented the former Chicagoan’s new life in suburban McHenry County.

Generations of Caldwells would eventually pass through the office’s doors as attorneys, including Bill’s brother and retired McHenry County Judge Michael Caldwell, and his daughter. Bill Caldwell closed the office for good last year.

“I actually got to work on a couple cases with my dad and even appear in court with him just in the last couple months,” Laura Caldwell said.

Following in her father’s footsteps, author Laura Caldwell went on to work as a civil trial attorney and the founding director of Life After Innocence, which offers re-entry assistance for the wrongfully convicted.

In more recent years, Bill Caldwell served as one of the attorneys representing the multimillionaire Cancer Treatment Centers of America founder, Richard Stephenson, in his divorce from his ex-wife, Alicia Stephenson.

“They call lawyers counselors,” Laura Caldwell said. “I don’t know that a lot of them fulfill that role these days, but he really did.”

A person didn’t need to be a relative of Bill Caldwell’s to glean inspiration from his career, however. Attorney Ed Donahue of the the McHenry-based firm Donahue and Walsh had never even met Bill Caldwell when Donahue chased him in the courthouse parking just to pick his brain.

“When I came out here 30 years ago, he was one of the lawyers you tried to emulate,” Donahue said. “I remember when I first came out to McHenry County, I watched Bill try a case and I literally chased him down in the parking lot to ask him about a trial.”

Bill Caldwell obliged and answered each of Donahue’s questions, the attorney said.

“He was always a complete gentleman,” Donahue said. “He was a great lawyer, and more importantly a great human being.”

Law was an inseparable part of Bill Caldwell’s identity, but there was much more to the man whom Laura Caldwell remembers as a “ferocious reader,” “active dad” and “man of ritual.”

“He was a very available dad,” Laura Caldwell said. “He was the kind of dad who sat through many a French horn concert and my sister’s Irish dancing.”

At other times, Bill Caldwell could be found relaxing in a hammock with a good book, walking one of the family poodles or skiing in the Colorado snow.

“He used to take us out to Colorado and ski and he always loved getting one or two ski trips a year,” Laura Caldwell said. “He just loved being outside.”

A former Marian Central Catholic junior varsity football coach, Bill Caldwell also reigned as the school’s first homecoming king. Whether he was watching his daughter cheerlead on the sidelines, or scouting new talent for the varsity football team, Caldwell was very much a cheerleader in his own right, Laura Caldwell said.

“I think people found that he was just very encouraging,” Laura Caldwell said. “’You can do this, you can get this done.’ In general, he seemed to be able to encourage a lot of people to pick things up and start over.”