The claim is misleading because while President Trump has publicly described protests in Portland and Chicago as involving insurrectionists and has deployed troops to these cities, there is no verified evidence that these protesters are 'left-wing paid insurrectionists' as a confirmed fact; the characterization is largely based on Trump's rhetoric without independent confirmation.
President Trump confirms that Portland and Chicago are overrun with left-wing paid insurrectionists.

Donald Trump says he is deploying troops to Portland, Oregon - Portland | The Guardian
Source: theguardian.com
Key Evidence
Trump has authorized troop deployments to Portland and Chicago amid protests.
theguardian.comtheguardian.comDonald Trump says he is deploying troops to Portland, Oregon
cnn.comcnn.comOregon: Judge temporarily blocks Trump’s National Guard deployment in Portland
He has used strong rhetoric calling some protesters agitators or insurrectionists but without independent proof of payment or organized left-wing insurrection.
trump.news-pravda.comtrump.news-pravda.comBREAKING - PRESIDENT TRUMP GOES OFF: "Portland is burning to the GROUND
pbs.orgpbs.orgWATCH: Trump accuses some Los Angeles protesters of being 'paid...
Courts have blocked some of Trump's deployment efforts citing legal concerns, showing contested federal responses rather than clear evidence of insurrection.
nytimes.comnytimes.comJudge Blocks Trump’s Deployment of National Guard in Portland, Ore
foxnews.comfoxnews.comCourt halts Trump's National Guard deployment to Portland, Oregon, with TRO
What the Evidence Shows
Multiple sources confirm that President Donald Trump has taken aggressive actions regarding protests in Portland, Oregon, and Chicago, Illinois, including deploying National Guard troops and federal agents to manage unrest.theguardian.comtheguardian.comDonald Trump says he is deploying troops to Portland, Oregon
thehill.comthehill.comDonald Trump's National Guard move in Portland sparks backlash Trump has expressed strong language about the protests, describing them as violent and involving agitators or insurrectionists.+3 more However, the specific claim that these protesters are 'left-wing paid insurrectionists' lacks independent verification. The sources do not provide evidence that the protesters are paid or organized insurrectionists affiliated with left-wing groups. Instead, the descriptions come from Trump's statements and political rhetoric.
Judicial pushback against some of Trump's deployment efforts in Portland indicates controversy over the federal response but does not validate the claim about paid insurrectionists.nytimes.comnytimes.comJudge Blocks Trump’s Deployment of National Guard in Portland, Ore
foxnews.comfoxnews.comCourt halts Trump's National Guard deployment to Portland, Oregon, with TRO Coverage from more neutral or critical outlets notes that protests have been ongoing with varying characterizations, sometimes described as chaotic or absurd rather than a coordinated insurrection. Additionally, Trump's accusation of 'paid insurrectionists' was explicitly made regarding Los Angeles protesters in a separate context, not directly confirmed for Portland or Chicago.+3 more
Therefore, while Trump's statements confirm his view and actions against protestors in these cities, the assertion that Portland and Chicago are 'overrun with left-wing paid insurrectionists' is an unverified political claim rather than an established fact.