Shortly after moving to Wisconsin, Troupis became a prominent lawyer for the
Republican Party of Wisconsin. He was one of the lead attorneys for the Republican Party in 1992 litigation over
redistricting, culminating in the federal court case , The named plaintiff in that case was Troupis' client,
David Prosser Jr., then the Republican minority leader in the
Wisconsin State Assembly. In 2001, Troupis applied for appointment to a newly created federal judgeship in the
United States District Court for the Eastern District of Wisconsin. That appointment ultimately went to
William C. Griesbach. Troupis again represented Republican legislators in litigation for the 2000 redistricting cycle. In this cycle, he petitioned for the
Wisconsin Supreme Court to take jurisdiction over the redistricting case, hoping this time to avoid a map drawn by the federal court. In the case of
Jensen v. Wisconsin State Elections Board, , the Wisconsin Supreme Court declined the case in a per curiam opinion. The maps were eventually redrawn by a federal court panel, in the case . Through the following decade, Troupis was involved in more litigation on behalf of the state Republican Party. He represented state senator
Joe Leibham in a recount of his senate election in 2002. Leibham sought federal intervention to set uniform counting standards, and prevailed by 46 votes. In 2007, Troupis represented recently elected conservative Wisconsin Supreme Court justice
Annette Ziegler after she was accused of violating the state code of judicial ethics. In her ten years as a circuit judge, Ziegler had ruled on more than 30 cases in which she or her husband had a direct financial interest. Ziegler settled the case with the state Ethics Board for $17,000, and Troupis then represented her at a hearing before three state Court of Appeals judges assigned to adjudicate the ethics complaint. Troupis reassured the judges that she would not make that mistake again. The panel ultimately recommended a reprimand; the Wisconsin Supreme Court then voted to reprimand her in a 5–1 decision. In 2008, Troupis represented the state Republican Party as an intervenor in the state Attorney General's lawsuit to force the state elections board to implement more strict voter identification rules before the
2008 United States presidential election. The lawsuit was dismissed in October 2008. The next year, he represented former state Veterans Affairs Secretary John Scocos in a lawsuit against the state Veterans Affairs Board over his firing. Discovery in the lawsuit revealed that the board had agreed to fire him a week before taking action and had coordinated their communications with the governor's office, technically a violation of the state open meetings laws. In 2011, Troupis represented David Prosser again. The former Assembly speaker was, by then, a justice of the
Wisconsin Supreme Court. After a narrow re-election victory in April 2010, Prosser retained Troupis as legal counsel to handle any challenges arising from the close election. At the same time, Troupis was involved in litigation before the state Supreme Court. He was then representing
Tea Party groups which sought to strike down new state campaign finance rules. But his primary business in that legislative session was, again, the redistricting process. For the first time in decades, Republicans held full control of state government for redistricting; the map they passed became infamous as one of the most dramatic gerrymanders in American history. Troupis worked on the legal strategy around crafting, passing, and defending the map. He coordinated an unprecedented non-disclosure process in which nearly all of the state's Republican lawmakers signed an agreement not to comment on the redistricting plan before the maps were released. Litigation followed the passage of the maps. In the case,
Baldus v. Members of the Wisconsin Government Accountability Board, Troupis tried unsuccessfully to avoid being deposed, asserting attorney-client privilege over the redistricting process. The case ultimately led to minor revisions in the map. In 2015, Governor
Scott Walker appointed Troupis to serve as a
Wisconsin circuit court judge in
Dane County. Shortly after taking office, Troupis announced he would not run for election to a full term in the overwhelmingly Democratic county. Following the sudden death of Wisconsin Supreme Court justice
N. Patrick Crooks in October 2015, Troupis sought appointment to succeed him. That position ultimately went to Walker ally
Rebecca Bradley. The following April, Troupis' longtime ally David Prosser announced he would retire from the Wisconsin Supreme Court in the middle of his term. Troupis again sought appointment, and ultimately resigned his judgeship in May 2016 while pursuing the position. Troupis was passed over again, as Walker appointed attorney
Daniel Kelly. In 2021, at the urging of chief justice Annette Ziegler, Troupis' former client, the Wisconsin Supreme Court voted to appoint him to the state Judicial Conduct Advisory Committee. That committee provides informal advisory opinions to state judges on compliance with the code of judicial conduct.
Trump campaign and indictment Days after the
2020 United States presidential election, Troupis began working on behalf of
Donald Trump and
his campaign's efforts to challenge the results in Wisconsin, where the unofficial tally then showed Trump losing the state by about 21,000 votes. He initially represented the campaign in a recount effort, but it resulted in almost no change to the election outcome. He also participated in litigation to the Wisconsin Supreme Court, which was also unsuccessful. On November 18, 2020, Trump attorney
Kenneth Chesebro emailed Troupis and other lawyers for the Trump campaign a memo in which he advocated that Trump's Wisconsin electoral slate should meet and produce
alternate electoral paperwork which could possibly be used to replace or nullify the official Wisconsin electoral votes during the January 6, 2021, counting of the electoral votes. Chesebro and Troupis continued to discuss the plan with other Trump attorneys and aides over the course of the next several weeks, as the plan was expanded from Wisconsin to other states with close election results.
Rudy Giuliani and
Boris Epshteyn then requested that Troupis and Chesebro draft alternate electoral certificates for Pennsylvania, Georgia, Michigan, Arizona, Nevada and New Mexico. The day before the electors prescribed meeting day, December 13, 2020, Chesebro again messaged Troupis and told him that national figures in Trump's campaign understood that this [alternate elector plan] would not be happening without Troupis having pushed for it. The Wisconsin Supreme Court ultimately ruled against Trump on December 14, the same day the electors met. Troupis and Chesebro then flew to
Washington, D.C., and met with Donald Trump at the
White House. Days later, Trump made his call for a rally on the
National Mall on January 6, 2021. Troupis later communicated with Wisconsin's Republican U.S. senator
Ron Johnson and his chief of staff about how to get the alternate electoral documents to Vice President
Mike Pence on January 6. As rioters were
breaching the
United States Capitol on January 6, Troupis texted Chesebro, "History is made!" Troupis and Chesebro subsequently settled the Law Forward litigation in March 2024, turning over additional documents to the plaintiffs and agreeing not to participate in a similar scheme again. On June 4, 2024, Troupis was
indicted in Wisconsin on a single felony
conspiracy charge, alongside Chesebro and Trump campaign aide
Mike Roman. Subsequently, the Wisconsin Supreme Court voted to suspend Troupis from his role on the state's Judicial Conduct Advisory Committee. ==Personal life and family==