The outlook for Walgreens Boots Alliance keeps darkening with CEO Tim Wentworth presenting investors with an uncertain picture filled with headwinds. Crain’s health care reporter Katherine Davis talks with host Amy Guth about challenges ahead for the pharmacy giant — plus, an update on Howard Brown Health.

Plus: Weeks after bombshell report, Guaranteed Rate board hasn't met to discuss founder's leadership; Deere reportedly laying off hundreds amid decline in farming demand; dealerships sue CDK for 'negligence in protecting users of its systems,' downtown arts college shutting down; and developer nears $1B refinancing for portfolio that includes 5 Chicago towers.