President Donald Trump is facing one significant failure after another, and at least one former conservative is mocking his repeated setbacks amid his fixation on "winning."

Ex-conservative columnist Jennifer Rubin wrote in her Monday column for "The Contrarian" that Trump simply cannot stop "losing." She said the president is not only under fire for his performance at the White House Correspondents' Dinner, as critics have argued, but is also continuing to lose in the courts and at the polls.

Several polls released last week showed how poorly Trump and Republicans are doing with fewer than 100 days until the midterm elections. DDHQ chief elections analyst Geoffrey Skelley told The Hill's Julia Mueller on Sunday that both chambers are now officially in play. For much of the summer, it was assumed the House would likely flip, but the Senate is now also in play as the Iran war drags on and gas prices rise again. Reports have said Republicans are in panic mode.

Meanwhile, Rubin said Trump is "burying them in new taxes (tariffs) that worsen their struggle to get by, and plundering the treasury to glorify himself with garish monuments and tacky tributes that have marred the nation’s capitol."

Legal defeats are mounting as well, and they have not been simple losses; in Rubin's view, they have also produced rebukes for the Justice Department from judges.

One case unfolded last week when The New York Times prevailed in its ongoing fight with the administration over demands for reporters' and their families' phone records. In that case, the judge gave the DOJ the choice of withdrawing its subpoenas or risk having them all quashed. The judge also sharply criticized a prosecutor who tried to bypass him to seek approval from another judge.

That development adds to what Rubin called "a truly stunning victory" in which Democratic state governors managed to block the MAGA-aligned media purchase of Warner Bros. Discovery by "Trump sycophant David Ellison." The merger is now on hold until June 2027, when the matter is expected to go to court. The Ellisons have already purchased CBS/Paramount and now plan to merge it with Discovery and Warner Bros. Rubin's colleague, Norm Eisen, also filed a lawsuit in the U.K. over the merger, she said on BlueSky Monday.

"The dramatic consolidation of news and entertainment businesses under the auspices of a MAGA mogul who expressly sought to curry favor with Trump had seemed like a done deal just weeks ago; now it may come to naught thanks to a major public campaign by the media/entertainment community and the diligent efforts of state AGs determined not to allow the feckless Department of Justice have the last say," Rubin said.

Trump also abandoned his effort to subpoena a list of Jewish people at the University of Pennsylvania as part of a lawsuit that has been underway for a year. Politico reported: “Court documents filed Thursday reveal that the Equal Employment Opportunity Commission and the university reached an agreement in which the agency will not enforce its subpoena seeking information on university employees.”

Rubin also pointed to the Justice Department's 17th consecutive loss. That case is part of Trump's demand that states turn over all of their election rolls. The assumption is that the White House wants to search the rolls to determine whether undocumented immigrants are registered to vote and to use voting records to locate them or accuse them of voting illegally.

"District Judge Claria Horn Boom, the eighth Trump appointee to slap down this effort, cited a Sixth Circuit ruling rebuking the Trump voting intimidation scheme," Rubin wrote.

The developments come as four more American soldiers were killed as a result of the Iran war. The election is 99 days away from Monday.