
Is Chicago About to Hit Rock Bottom?Nov 21
after decades of corruption and chronic mismanagement, chicago might be ready to admit it has a problem — and its far-left crony mayor pushing the city to the brink might trigger a revival
Oct 30, 2025

In 2024, Boston’s commercial property sector was struggling. Office occupancy and retail volume hadn’t fully recovered from the pandemic,1 and market values were believed to be substantially below official city assessments. The city, which derives 35 percent of its revenue from commercial property taxes, was projected to face a $1.5b shortfall.
Increasing residential tax rates would anger voters and likely cost votes in the upcoming election, though residential valuations were seeing strong growth; increasing commercial tax rates would further depress valuations and could therefore decrease aggregate receipts.
Mayor Michelle Wu, ignoring the warnings of think tanks and business leaders, chose the riskier commercial tax hike strategy, for which she needed the approval of the state legislature. Office towers don’t vote, after all. And when the legislature rejected her proposal, citing the risk it posed to the city’s economy and that of the state as a whole, Wu’s assessing department took a different approach. First, it assigned the commercial properties in question valuations that exceeded any fair market value. Second, when the owners of these properties appealed their assessments, the assessing department “quietly and systematically increas[ed] property tax assessments” on the properties under appeal.
This was an unconstitutional but hard-to-prove act of retaliation, seemingly designed to bring property owners to heel and deter future attempts to push for fair assessments.
The assessment case is ongoing, and it’s just one illustrative example among many of Mayor Wu’s broader approach to governance: prioritize the interests of your supporters (whether they be voters or private interest groups) above the economic health of the city and the rule of law within it.