Sherwood was a retired CIA officer who had recruited spies for the United States government and had been involved with the agency's operations in Cuba. He moved to Boulder in 1981. In 1997, he began a new life as a local activist for campaign-finance reform by running, unsuccessfully, for a seat on the Boulder City Council. Two years later he was victorious in an effort, along with fellow reformer Mark Ruzzin, to bring a citizens' initiative to the voters that authorized the City of Boulder to help fund local candidates who agree to limit their election spending.
Ruzzin, who became close to Sherwood while working on the effort and was one of the last people to see him alive, says he knew nothing of his friend's legal troubles. "He was a great man," Ruzzin told the Boulder Daily Camera after learning of Sherwood's death. "He cared very much about the community and making it a better place."
But while the public was hearing all about Sherwood's crusade for campaign-spending caps, the Boulder police were also becoming well acquainted with him. On April 23, 1998, a 51-year-old Boulder woman filed a restraining order against Sherwood. The woman (who didn't want her name used in this story and wouldn't comment on Sherwood, because she says she doesn't want to sully the image that's been painted of him in the press, and because she is afraid of retribution) told police that Sherwood had been stalking her, sending her unwanted flowers and postcards, riding his bike down her street and lingering outside her house.
The restraining order prohibited Sherwood from coming within one hundred yards of her, but according to Boulder police records, Sherwood violated the order on May 16, 1998, and again on May 22, when he rode by the woman's house on his bike. A neighbor saw Sherwood near the woman's home on those two dates and provided police with a written statement. On May 29, 1998, Sherwood sent the woman a letter saying that he would appeal the restraining order "to the U.S. Supreme Court, if necessary." The reporting officer noted, "He states that his intent is to make clear what he believes is at stake in this matter, that being his integrity."
On June 9, 1998, Boulder Police Detective K. Yamaguchi issued Sherwood a summons for violating the restraining order. In the police report, Yamaguchi detailed a June 8 phone call with Sherwood. "During my conversation with Sherwood, I learned the following: Sherwood acknowledged knowing [the victim]; Sherwood confirmed that he had been served a copy of a restraining order prohibiting him from contacting [the victim]; Sherwood confirmed writing and mailing the letter to [the victim] regarding his desire to appeal the restraining order; Sherwood denied riding his bike near [the victim's] residence; Sherwood strongly believed that the restraining order was improperly issued and will appeal the judge's ruling. According to the victim and suspect, Sherwood has never threatened physical violence against [the victim]. They have not been involved in an intimate relationship."
The exact nature of their relationship is unclear, but according to the incident summary written by the reporting officer, the woman "is concerned that Sherwood has not ceased his efforts to remain a presence in her life."
Sherwood continued that unwanted presence in September 1998, when he ran into the woman at an art exhibit at the Boulder Public Library. Advertisements for the exhibit had listed the woman as a participant. "Sherwood attended this event and [the victim] told us that she saw him 'four times in a 45-minute time span,'" reads another police report. "She avoided eye contact with Sherwood and did not speak to him. [She] feels that Sherwood knew that she was there and purposely attended for that reason."
Because Sherwood was appealing the restraining order, the woman waited until November to file the police report. Later that month, a detective called Sherwood to inform him that an arrest warrant was on file, but Sherwood wasn't home; Sherwood later called the detective back and left a message saying that he did not go to the art exhibit to see the woman and that he made no attempt to speak to her or to follow her. "In his message, Sherwood asked what he was supposed to do, if every place in Boulder he has to look over his shoulder and under his armpit. Sherwood said this is driving him crazy and that he is very upset... Sherwood also stated that nothing ever happened between him and [the victim] and that she made it all up," the report states.
On December 1, 1998, Sherwood turned himself in to the police, who arrested him for violating the restraining order.
Almost two years later, in October 2000, Sherwood apparently returned to the woman's home. She noticed him staring at her from approximately 75 feet away while she was in her front yard. When she yelled at him to leave, he started walking toward her, according to another report, and she ran into her house and called police, who later searched the neighborhood but found no trace of Sherwood. The authorities didn't leave empty-handed, though; the woman gave them seven unsigned postcards that she said were from Sherwood. One was sent from Scotland, one invited her on a trip to Spain. In one note, the author wrote, "You consist of exactly the right combination of qualities so that the juvenile archer's arrow with your name on it penetrated deep into mind and feeling, releasing huge flows of energy that had been stored to be put to good use with just such a combination... Sure, no matter how I twist and turn it, nor whomever I may squire about, I can't extract the arrow. I'm stuck with loving you saeculae saeculorum [forever]."
Another postcard reads: "Not once in the past decade have I seen you at the trailhead. Only once were you even in the area... Gave me a start this morning. Also, pained me a bit to note the revulsion on your face. You must know I go to some lengths to keep my disgusting self (your somewhat puzzling characterization of this rickety creature) out of your face. To spare you such unpleasantness, a reminder that I run the trail mornings and sometimes evenings until weather is no longer indulgent. Should you ever find relief from your Johnaphobia, may I assume you'll give me some sort of sign?"
Over the next few months, police investigated the woman's complaints. But Sherwood won his appeal: A Boulder District Court judge dismissed the restraining order "due to legal issues surrounding the language of the statute." Still, the investigating officer was concerned. "Although a restraining order was now not in effect, Sherwood had continued a pattern of following, sending cards and flowers and surveilling her," the officer wrote. "[The victim] told me that this has caused her severe emotional distress prompting her to seek and obtain psychiatric counseling."
In March 2001, five months after Sherwood was reported to have shown up at the woman's house, he was issued a felony summons, arrested and charged with harassment.
After police completed their investigation, they handed over their files to Boulder Deputy District Attorney Kathy Delgado, who determined that there was probable cause for issuing Sherwood a summons for stalking. "I talked to [the victim] about what she wanted," Delgado says. "All she wanted was for there to be a permanent restraining order; she didn't want him to go to jail."
Sherwood met with the DA's office and agreed to abide by the terms of a new restraining order, issued on May 25, which again prohibited him from coming within one hundred yards of the woman. In return, Delgado dismissed the stalking case. But on July 8, just a week before he committed suicide, Sherwood rode his bike by the woman's home one last time. The woman saw Sherwood as she happened to be riding her bike on the same street in the opposite direction, and she returned home to call the police. When an officer later spotted and stopped Sherwood on the University of Colorado campus, he "stated that he has taken this route for fifteen years. Sherwood also stated that he rides his bike to the trail and runs the path. Sherwood was aware of the restraining order against him... He didn't think the restraining order included her home when he was just riding his bike on a public street."
That day, Sherwood was arrested for the fourth and final time. He was released on July 9 after posting a $500 bond. Sherwood's past arrests didn't result in a trial because the previous restraining order wasn't considered valid while it was being appealed. This time, however, he was going to have to choose between agreeing to a plea bargain or arguing his case, publicly, before a jury of his peers. Sherwood never made that decision.
Sherwood's family members -- he is survived by his ex-wife, from whom he had been divorced for 25 years, two daughters in Colorado, two sons in California and five granddaughters -- have reviewed the police records in the three weeks since Sherwood killed himself, and they don't believe his legal troubles are to blame for his suicide.
"He told my mom twenty years ago that when he was done with life he'd jump off a cliff," says Sherwood's daughter Kimberley Sherwood, who adds that she didn't know about the arrests until after her father's death. "You can't know for sure. It's all speculation, but all I can go on is his letter, in which he talked about his health. There was no reference to this court stuff anywhere. If it had been a concern to him, I think he would have said something."
His other daughter, Jessica Sherwood, agrees. "I really think the timing is coincidental. He was a private person, but he did share stuff with us," she says. "I really think he would have hinted at it if it had been a factor at all."
Sherwood's friends didn't know about his criminal record either, before or after his death.
Daily Camera columnist Clint Talbott published a glowing tribute to Sherwood on July 19 titled, "Letter to an icon." In it, he wrote, "Dear John, We know it was important for you to be fit. Pedaling your bike through Boulder, stocking up at Whole Foods, trouncing an opponent in tennis, you were healthier than some folks half your age. So your knees were rickety, and your eyes were fading. Minor travails for a man of 76. Nothing to get overwrought about. Certainly not enough to propel you off a cliff. Obviously, you did not agree."
And, in fact, some have advanced theories about his death that have nothing to do with Sherwood's health or his legal problems; conspiracy theorists from Boulder and beyond are now musing over whether Sherwood's death was linked to his former intelligence work. In an article published in the July 19 edition of the Boulder Weekly, Boulder City Councilman Spense Havlick, who described himself as Sherwood's close friend and "soul mate," said the police should "examine this note carefully to be sure it was his and not written under duress, to assure no foul play is at work here."
Sherwood's daughters dismiss the conspiracy theories as ridiculous and remain convinced that their father's failing health was the only factor in his suicide.
"People have told me that they were just playing tennis with my father the other day and he seemed fine," Jessica explains. "But he had his own perception of his physical and mental decline. He held himself to a high standard. People can theorize about this all they want, but the fact is, he was ready to die."
