In 2004, Diamond entered third party politics. He ran simultaneously for the U.S. House of Representatives and the state legislature as a Libertarian Party candidate. He was defeated in both races. In 2005, after members of the state legislature voted themselves a pay raise during a midnight session, Diamond created PACleanSweep.com, a website dedicated to ousting every incumbent legislator in the state. PACleanSweep eventually found candidates for two State Senate districts and 44 State House Districts. On May 16, 2006, the day of the primary election, 35 of the CleanSweep candidates won their primaries. 16 of the winners were running in contested races and 7 of them defeated incumbents. Diamond was named one of three "Citizens of the Year" by The Philadelphia Inquirer on January 1, 2006, for his efforts to defeat the incumbents.
Gubernatorial run
In 2006, Diamond ran for governor as an Independent. Diamond advocated abolishing the property tax, funding public education out of general revenues, auditing all government expenditures for efficiency and usefulness, calling a constitutional convention to modernize the state's constitution, repealing legalized slot machines, and "stimulat economic development" by reducing taxes and regulation. He promised to serve only one term and not run for re-election. He selected Tom Lingenfelter, a former Republican state committeeman and Democratic candidate for Congress run with him for Lieutenant Governor. Diamond abandoned his run when he fell well short of the signature requirements to qualify for the statewide ballot.
Personal Controversy
Two women filed for and were granted Protection From Abuse orders against Diamond, in 2002 and 2013, respectively. In both cases, the orders were withdrawn months later. Court documents state that one woman claimed Diamond "pushed her in the face seven times and scratched her under an eye" and "threatened to kill her if she disconnected the cable". The second woman to file for a PFA against Diamond told the courts that when she wouldn't leave his apartment,"he knocked her down and dragged her to the doorway." Diamond was later fined $200 for violating the second order. In 2014, members of the Lebanon County Republican Committee sent Diamond a letter asking him to withdraw from the race for House of Representatives, citing his "string of unsuccessful runs for office" and the apparent history of violence evidenced in court documents. Diamond responded by saying no one should be discussing orders that were dismissed, no matter whether it took "six months or one day" for the women to change their minds. He continued: "This was a long time ago...all is fair in love, war and politics. But let's talk about the truth, the whole truth, and nothing but the truth. Let's not cherry-pick just to make the other guy look bad." Lebanon County District Attorney David Arnold Jr. also made a public statement about the letter, saying: "It's not as simple as them being filed and then the next day, someone realized they made a mistake and they were withdrawn...to me, that's a disturbing pattern of behavior with this guy...but he admits no culpability and makes light of it." In fall of 2015, Diamond admitted to being an alcoholic after being cited for public intoxication. In July 2020, Diamond plagiarized a statement by a doctor speaking against transphobia, replacing the term "LGBTQ" with the word "unmasked" as a way to allege discrimination of those who refuse to wear masks during the Covid-19 pandemic.
Schism with PACleanSweep and the Reform Movement
Critics point to efforts by Diamond to prevent PACleanSweep from searching for gubernatorial candidates as evidence that Diamond planned to seek office from the start. In March 2006, Diamond attempted to remove five of the ten members of PACleanSweep's Board of Directors. Diamond requested the resignations of all board members, and cut off access to those who refused. Ironically, Diamond continued to operate PACleanSweep, with the assistance of board members who had submitted their resignations, over the protests of many in the reform movement. Diamond would later attempt to add four individuals to the group's board, and then resigned in April 2006 to run for governor. In April 2006, several members of PACleanSweep's Board of Directors represented by attorney Charles A. Pascal, Jr., sued Diamond for violating nonprofit corporation law and the organization's charter. A Lebanon County judge declared that the four board members Diamond attempted to add were not legal directors of PACleanSweep, and ordered that corporate access and voting rights be returned to the rightful Board of Directors.
Current status
With PACleanSweep's Board of Directors now divided, Diamond then attempted to change the voting structure by granting himself and Lingenfelter voting rights, despite a unanimously-passed corporate policy that prohibited political candidates from exercising control of the corporation. When this move failed, Diamond and his supporters attempted to disband the corporation entirely. He was unable to garner even a simple majority for dissolution. Diamond and four others then refused to discuss business with the organization's other board members, and filed court papers seeking the involuntary dissolution of corporation. A hearing was held on August 7, 2006, in Lebanon, Pennsylvania, where a judge granted the motion to dissolve PACleanSweep. Inc. Diamond continues to operate a website, PACleanSweep.com, suggesting that the dissolution attempt was simply a means to undermine the clout of Diamond's personal detractors.
2008 campaign for the State House
Diamond challenged Republican incumbent Mauree Gingrich for the 101st district in the 2008 election. On April 22, 2008, he finished second in a three-way Republican primary behind Gingrich with 22.9 percent of the vote.
Candidacy for Lieutenant Governor
Diamond made a bid for candidacy in the 2010 Lieutenant Governor race. He garnered 4.5% of the votes in the Republican primary.
2014 Campaign for the State House
Diamond successfully ran for the 102nd district after being endorsed by retiring representative RoseMarie Swanger. The campaign was contentious and controversial. Diamond's supporters filed legal challenges against the campaigns of Joe Eisenhauer and Wanda Bechtold. Eisenhauer was removed from the ballot for failing to file a financial statement, while Bechtold's nominating petition was found defective. As a result of these challenges, Diamond was the only candidate on the ballot in the May primary. Unopposed, he won the Republican primary with 56.7 percent of the vote, while Democrat Jake Long won the Democratic primary as a write-in. Diamond won the general election with 45 percent of the vote, defeating Democrat Jake Long, Independent Robert McAteer, and Bechtold, who ran as a write-in candidate.
