The claim that a judge named Simon has set a restraining order hearing for tonight regarding Trump's deployment of the National Guard to Oregon is mostly true because multiple sources confirm Oregon's legal efforts to block the deployment and request a temporary restraining order, though none explicitly name Judge Simon or specify the hearing timing as 'tonight'.
Judge Simon sets a restraining order hearing for TONIGHT on Trump's deployment of the National Guard to Oregon. Suggests he could issue a very quick order to stop Trump from going into Portland!

Following suit against Trump, Oregon asks judge to issue order blocking Guard deployment • Oregon Capital Chronicle
Source: oregoncapitalchronicle.com
Key Evidence
Oregon's Department of Justice has filed a temporary restraining order request to block Trump's deployment of National Guard troops to Portland.
oregoncapitalchronicle.comoregoncapitalchronicle.comFollowing suit against Trump, Oregon asks judge to issue order blocking Guard...
opb.orgopb.orgTrump administration authorizes 200 National Guard members for Portland...
Multiple news outlets report ongoing lawsuits challenging Trump's federalization of state National Guards as illegal.
nbcnews.comnbcnews.comOregon sues Trump administration over deployment of National Guard troops to...
foxnews.comfoxnews.comOregon files lawsuit to block Trump's National Guard deployment to Portland
Prior rulings in California have found Trump's deployments unlawful, indicating courts are actively involved in such cases.
pbs.orgpbs.orgTrump must return control of California National Guard to the state, judge rules
calmatters.orgcalmatters.orgTrump broke the law by sending National Guard to L.A., federal judge rules
What the Evidence Shows
Multiple credible sources report that the state of Oregon, including its Department of Justice and Attorney General, has filed a lawsuit and requested a temporary restraining order to block President Donald Trump's federalization and deployment of approximately 200 National Guard troops to Portland, Oregon. This legal action is part of a broader challenge against the Trump administration's use of Title 10 authority to federalize state National Guard troops, which Oregon argues is illegal and unconstitutional. Several news outlets (Oregon Capital Chronicle, OPB, NBC News, Fox News, The Guardian) confirm the filing of this lawsuit and the request for an injunction to stop the deployment.
However, none of the sources explicitly mention a judge named Simon or confirm that a hearing is scheduled specifically for 'tonight' (September 29, 2025). The reports do indicate that the case is active and that courts have previously ruled against similar deployments by Trump in other states (California), suggesting that quick judicial actions such as temporary restraining orders are plausible. Still, the exact timing and judge's name remain unverified in these sources.
Therefore, while the core facts about Oregon seeking judicial intervention to block Trump's National Guard deployment are well-supported, the specific details about Judge Simon setting a hearing for tonight and suggesting an imminent order are not confirmed by available evidence.