1970s to mid-1980s — Douglas Bruce, a Los Angeles native, earns his law degree and practices for several years, before turning to real estate. He runs for the California State Assembly as a Democrat. He loses.
1986 — Bruce moves to Colorado Springs.
Fall 1988 — Bruce tries to petition his first version of the Taxpayer's Bill of Rights (TABOR, Amendment 6) onto the state ballot, but Secretary of State Natalie Meyer denies him for lack of valid signatures, forcing Bruce to gather more.
November 1988 — Amendment 6 is defeated.
November 1990 — Bruce's second version of TABOR, "Amendment 1," makes the 1990 state ballot and loses. Bruce blames his personality, telling the Gazette-Telegraph, "Some people said we needed a kinder, gentler person to push this amendment. I'm sorry Pee-Wee Herman wasn't available."
April 1991 — Bruce's retooled local version of TABOR passes in Colorado Springs. Bruce tells the G-T: "If I can give the Legislature two little pieces of advice, it's: You're next!"
August 1991 — Mayor Bob Isaac tells Bruce, "If you were a man, I'd take you out," following a dispute at City Council chambers over the city's intention to exempt city enterprises from TABOR. Bruce replies, "If it helps you any, I'll drop my pants."
Winter 1991 — Bruce tries TABOR a third time, as well as an election-reform issue. Meyer allows TABOR on the ballot.
November 1992 — Colorado voters approve a statewide TABOR amendment to the Colorado constitution.
Winter 1992 — Bruce claims TABOR will eliminate many government contracts. He threatens to sue various districts that raise taxes without voter approval. State Sen. Regis Groff is applauded by the Senate after calling Bruce a "fraud."
Spring 1993 — Bruce sues the city several times over TABOR issues.
August 1993 — Bruce is convicted of four misdemeanor violations of owning an unsafe building in Denver, where he has many properties. He's fined $2,400 and ordered to perform 150 hours of community service. It's the beginning of a 20-plus year saga for Bruce, who will face more charges in Denver, Colorado Springs and Pueblo. At one point in 1995, Bruce spends a week in jail after being held in contempt of court.
November 1993 — Bruce tries to push a statewide election reform package that would streamline signature-gathering to petition issues to the ballot, make it easier to recall elected officials, and set new standards and penalties for campaign donations. Amendment 12 would require that officials assume petition-signers are registered voters until proven otherwise.
• Ballot issues pop up across the state asking voters to allow governments to keep tax money collected over the TABOR cap. The Colorado Municipal League later finds that between 1993 and 2008, Colorado municipalities asked voters to keep revenues collected over the TABOR cap 508 times. Voters approved 87 percent of those requests.
• Voters shoot down the state tourism tax, but uphold other taxes, especially for police, fire fighters, sewers and other priorities.
February 1994 — Bruce begins collecting signatures to change the city charter and prevent a city subsidy for building the World Arena, force the sale of city parking garages, phase out city funding of bus service, ban employee severance and bonuses, and create minimum expenditures on public improvements and public safety. It fails to make the ballot for lack of signatures.
May 1994 — City Council approves limiting future city ballot questions to a single subject. Bruce causes a scene at the Council meeting.
November 1994 — Voters overwhelmingly defeat Bruce's Amendment 12 and approve Referendum A, a statewide single-subject rule for ballot proposals that prevents Bruce from running a question like TABOR again. Local governments around the state pass "de-Brucing" measures, making them immune from key TABOR provisions. Experts say Bruce's days of power are likely over.
June 1996 — Bruce challenges state Sen. Ray Powers. "There will never be anyone elected to the Legislature like me — if I'm elected," he tells the G-T. He loses.
Summer 1998 — Bruce's attempt to put tax-slashing measures on the state ballot are thrown out by the Colorado Supreme Court for breaking the single-subject rule.
Spring 1999 — The state Supreme Court throws out more tax-cutting Bruce ballot proposals.
July 1999 — Fed up, state lawmakers consider limiting the number of citizen-petitioned initiatives one applicant can submit to the state ballot. Bruce is responsible for 156 initiatives being considered for the November ballot. In February, Bruce is led out of a state Senate Judiciary Hearing after Sen. Gigi Dennis, R-Pueblo, accuses Bruce of threatening her.
February 2000 – The 10th Circuit Court of Appeals rules against Bruce, who claimed the single-subject rule was unconstitutional.
August 2000 – Bruce narrowly loses the GOP primary for state Senate District 10 to state Rep. Ron May, but not before following Republican Gov. Bill Owens, a noted enemy, down the street, shouting questions and dragging a little red wagon full of campaign materials behind him.
November 2000 — Voters reject a Bruce tax-cut plan, Amendment 21.
December 2001 — Bruce forms Active Citizens Together (ACT), the nonprofit that he'll eventually be convicted of funneling money through to avoid paying taxes.
May 2002 — Bruce and like-minded City Councilor Charles Wingate propose two city tax-cutting measures. Both are rejected for breaking the single-subject rule. Days later, they submit nine more ballot measures. A few days after that, Bruce submits seven more. Sixteen petitions are eventually approved, though Bruce and Wingate decide to pursue only three — then put off petitioning any.
February 2003 – Bruce plans to run for City Council with six personally selected others, to form a slate. But his idea falls apart when four candidates refuse to sign off on his plan, which includes eliminating city transit.
November 2004 — Bruce is elected county commissioner for District 2. Thirteen Republican officials who endorsed Bob Null, a write-in candidate, rather than Bruce, the official candidate, are asked to resign for breaking party rules. That request is eventually rescinded.
January 2005 — New Commissioner Bruce is upset when he fails to get the biggest office, and the county refuses to deposit his earnings, tax-free, into ACT. In November, Bruce settles with the county.
August 2005 — City Council members legally challenge Bruce ballot initiatives that would phase out city property tax, cut sales tax and end a controversial streetlight fee for Colorado Springs Utilities. After failing to get a judge to force the issue, Bruce asks the district attorney to file criminal charges against the Councilors.
November 2005 — Voters approve state Referendum C, a five-year timeout from spending limits set by TABOR. Bruce campaigned strongly against the measure.
August 2006 — The Colorado Court of Appeals sides with Bruce, ordering his tax-cut and debt-limitation initiatives onto the November city ballot. Issues 200 and 201 would limit the city's ability to borrow money and take away voters' right to choose whether the city can keep excess revenues. Both lose.
December 2007 — After Rep. Bill Cadman vacates House District 15 to fill a state Senate vacancy, Bruce is appointed to the seat by a Republican vacancy committee. Bruce announces that he doesn't want to be sworn in until after the legislative session starts, allowing him two extra years before he'd bump into term limits. Both parties respond angrily.
January 2008 — Bruce angers lawmakers again by demanding that the full House be seated when he's sworn in (late), and that he be allowed time for a speech. House Speaker Andrew Romanoff refuses to indulge Bruce's "vanity." Bruce is sworn in with only five other legislators in the chamber. He then famously kicks a Rocky Mountain News photographer who snaps a shot of him during morning prayer. The House considers expelling Bruce, which would require a two-thirds vote, and then votes nearly unanimously to censure Bruce — a historic first. Bruce refuses to apologize and compares himself to Jimmy Stewart in the 1939 film Mr. Smith Goes to Washington.
February 2008 — Bruce refuses to back a resolution honoring military veterans. Republican colleagues respond with scorn, then remove Bruce from the State, Veterans and Military Affairs Committee.
March 2008 — Mark Waller makes the primary ballot to challenge Bruce for the House District 15 seat.
April 2008 — Bruce refers to immigrant farm workers as "illiterate peasants" on the House floor, drawing gasps. Rep. Kathleen Curry, D-Gunnison, stops Bruce immediately, saying, "How dare you."
June 2008 — Bruce submits signatures for two city ballot proposals that would end the Stormwater Enterprise, and change the way other city enterprises are run, later verified as Questions 200 and 201.
August 2008 — Bruce loses the Republican primary to Waller.
November 2008 — Questions 200 and 201 are ditched by voters.
August 2009 — Bruce is ticketed for trespassing after collecting signatures for a city ballot measure at a local Costco, and refusing to leave. Costco doesn't allow solicitors and has warned Bruce in the past. A jury will acquit Bruce in December.
September 2009 — City Councilors allow Bruce's Measure 300 on the November ballot, despite Bruce's lateness turning in signatures. Bruce's initiative would phase out fees to city enterprises, eliminating the Stormwater Enterprise.
October 2009 — After being interrupted by Bruce, Vice Mayor Larry Small explodes on the dais, shouting, "Just shut up and let me have my say! You're an obnoxious, irritating individual. Now just shut up!"
November 2009 — Measure 300 passes. City leaders express confusion over the real effect, but vote 5-4 to end the stormwater fee at the end of the year. Bruce says it should end immediately. Council refuses to end payments from Utilities to the city.
January 2010 — Eight people who gathered signatures to put Amendments 60 and 61 and Proposition 101 on the state ballot are found to have lived in properties owned by Bruce. He denies any involvement in pushing the measures.
May 2010 — Bruce is ordered to serve as a witness in a campaign finance complaint involving the three state measures. He dodges being served 30 times, even as those proposing the initiative out him as the real muscle behind the campaigns. Bruce is accused of breaking state law by paying more than $200,000 for signature-gathering.
June 2010 — Attorney General John Suthers announces he will seek contempt sanctions against Bruce, who faces a second contempt charge, this time for ignoring two grand jury subpoenas from the 4th Judicial District. Bruce agrees to appear, and the contempt hearing is dropped. Bruce eventually agrees to cooperate after being granted immunity.
Summer 2010 — Bruce attempts to get a "strong mayor" issue on the April city ballot, but is sidetracked when Citizens for Accountable Leadership takes up the same cause.
November 2010 — Amendments 60 and 61 and Proposition 101 are defeated.
December 2010 — A legal hearing in Denver addresses allegations that Bruce's nonprofit, ACT, violated state law by spending more than $200,000 on the campaigns of 60, 61 and 101. Bruce doesn't show. Shortly afterward, Bruce dissolves ACT, and an administrative law judge fines ACT $11,300. Bruce claims the charity doesn't have funds to pay the fine, saying he was only the charity's bookkeeper.
February 2011 — Bruce announces that he will run for City Council alongside four allies who together call themselves the Reform Team.
• It's discovered that ACT did not properly disclose its political contributions for years.
March 2011 — Following an Independent story, Colorado Ethics Watch files a campaign finance complaint against the Reform Team, which has set up a political action committee to fund its campaign, sidelining reporting requirements.
April 2011 — Bruce's Reform Team loses. Days later, Bruce is arrested on charges of tax evasion after being indicted by a state grand jury for failing to pay taxes in 2005, 2006 and 2007. Bruce is accused of funneling money through ACT to avoid paying Uncle Sam. Bruce denies the charges.
May 2011 — Lawmakers file suit to have TABOR eliminated on the basis that it unconstitutionally eliminates representative government. On Wednesday, Feb. 15, the suit was scheduled to come before a judge who was expected to dismiss it.
June 2011 — The Bruce trial circus begins. Bruce tries to have the case dismissed, hamper the proceedings, suppress evidence against him and irritate the judge with long tirades. At one point, he says, "They would love nothing better than to strip Mr. Petition of his right to petition the government ... and put me in state prisons to be sodomized for 10 years." Denver District Court Judge Anne Mansfield grows so frustrated that she walks out of court one day.
• Bruce is accused of practicing law without a license and ordered to respond to the Colorado Supreme Court. Bruce says the claim is "illegal."
December 2011 — The trial begins, with Bruce charged with three felonies (tax evasion, filing a fraudulent return and attempting to deceive a public official) and a misdemeanor. Bruce shows up late to the first day of trial and launches into long attacks, portraying himself as a victim of government. His lengthy and heated speeches will characterize the trial.
• A jury finds Bruce guilty on all counts. His sentencing is set for Feb. 13. Bruce says he will appeal.
Feb. 13, 2012 — Bruce is sentenced to six months in Denver County Jail and six years probation, and is ordered to pay back taxes with interest, as well as prosecution costs. He calls himself a political prisoner.
Information sourced from previous reporting by the Colorado Springs Independent, the Gazette and the Denver Post.