2. Debt plus opioid overhangs: While a turnaround could potentially lead to Walgreens being a multi-bagger from here, there is also a non-zero chance of a total loss on one's investment, due to the company's debt load and opioid settlement payment overhangs. As of last quarter, the company had roughly $9 billion in debt, along with another $5.9 billion in opioid litigation settlement payments that Walgreens will have to pay out over time. With these overhanging liabilities, Walgreens is definitely on the clock to get its profitability in order.