What if you bought Walgreens in 2000?
US Health · Pharmacy. The hindsight answer, year by year, against the only benchmark that matters.
Could you have picked it? Play0.4× · S&P 500 same money: $4,626
$1,000 in Walgreens at the start of 2000 would be worth about $395 today. A plain S&P 500 index fund over the same years would have made more — the boring option won.
What happened: Walgreens was taken private in 2025.
The story
Walgreens was for decades the model American retailer: a drugstore on seemingly every busy corner, steady growth and a dividend raised year after year. The stock did little in the 2000s, then rallied in the early 2010s as the company merged with Europe's Alliance Boots, completed in 2014, under the dealmaker Stefano Pessina. It looked like the birth of a global pharmacy giant.
It was closer to a peak. Walgreens' partnership with the blood-testing start-up Theranos became an embarrassment, its attempt to buy Rite Aid was cut back under antitrust pressure, and reimbursement cuts, Amazon's arrival in pharmacy and falling front-of-store sales squeezed margins. A large bet on the primary-care chain VillageMD led to multibillion-dollar write-downs. In 2024 Walgreens was dropped from the Dow Jones Industrial Average, replaced by Amazon, and cut its long-cherished dividend. In 2025 the private equity firm Sycamore Partners agreed to take it private at a price far below its 2015 high. From the peak, investors lost most of their money; even from 2000 they ended well behind.
The lesson: A long record of dividend increases says little about the future when the underlying business is being disrupted, and a high yield can be a warning rather than a gift.
$1,000 invested at the start of each year
| Bought in | Price then | Worth today | S&P 500 would be | Multiple |
|---|---|---|---|---|
| 2000 | $29.00 | $395 | $4,626 | 0.4× |
| 2003 | $29.00 | $395 | $7,727 | 0.4× |
| 2005 | $38.00 | $301 | $5,763 | 0.3× |
| 2007 | $46.00 | $249 | $4,789 | 0.2× |
| 2008 | $38.00 | $301 | $4,626 | 0.3× |
| 2010 | $37.00 | $309 | $6,071 | 0.3× |
| 2012 | $33.00 | $347 | $5,312 | 0.3× |
| 2015 | $76.00 | $151 | $3,301 | 0.2× |
| 2018 | $73.00 | $157 | $2,519 | 0.2× |
| 2020 | $59.00 | $194 | $2,092 | 0.2× |
green = beat the S&P 500 · red = lost money
Best entry point in our set: 2000, turning $1,000 into $395. The S&P 500 from that same year: $4,626.
Now try it without hindsight. The wheel decides the year and the asset class, you pick the position, ten seconds a pick, and we simulate to today. Walgreens is one of 258 positions on the wheel — including the ones that went to zero.
Play Sixty-40More in US Health
- What if you bought Pfizer?
- What if you bought Johnson & Johnson?
- What if you bought Merck?
- What if you bought Eli Lilly?
- What if you bought Amgen?
- What if you bought Gilead?