What if you bought CVS in 2000?
US Health · Pharmacy. The hindsight answer, year by year, against the only benchmark that matters.
Could you have picked it? Play3.8× · S&P 500 same money: $4,626
$1,000 in CVS at the start of 2000 would be worth about $3,750 today. A plain S&P 500 index fund over the same years would have made more — the boring option won.
The story
CVS started as a pharmacy chain and spent two decades trying to become an entire healthcare system. In 2007 it merged with Caremark, a pharmacy benefit manager, and in 2014 it made headlines by stopping cigarette sales. In 2018 it bought the health insurer Aetna for about $70 billion, and it later added primary care with Oak Street Health. The idea was a single company covering insurance, prescriptions and clinics.
Shareholders have not yet been convinced. The stock peaked around 2015 and spent the following decade going nowhere, as reimbursement pressure squeezed drugstores, the Aetna debt weighed on the balance sheet, and Medicare Advantage costs rose faster than expected in 2024. The CEO was replaced that year, and the company announced store closures and cost cuts before a recovery in 2025. Over the full period, CVS still beat its rival Walgreens comfortably, but someone who bought in 2015 spent a decade with little to show for it. It illustrates how integrating many healthcare businesses does not automatically produce value for those who own the shares.
The lesson: Big acquisitions that sound strategically elegant can quietly destroy shareholder value when they are financed with debt and depend on regulatory goodwill.
$1,000 invested at the start of each year
| Bought in | Price then | Worth today | S&P 500 would be | Multiple |
|---|---|---|---|---|
| 2000 | $20.00 | $3,750 | $4,626 | 3.8× |
| 2003 | $25.00 | $3,000 | $7,727 | 3.0× |
| 2005 | $45.00 | $1,667 | $5,763 | 1.7× |
| 2007 | $30.00 | $2,500 | $4,789 | 2.5× |
| 2008 | $40.00 | $1,875 | $4,626 | 1.9× |
| 2010 | $32.00 | $2,344 | $6,071 | 2.3× |
| 2012 | $41.00 | $1,829 | $5,312 | 1.8× |
| 2015 | $96.00 | $781 | $3,301 | 0.8× |
| 2018 | $73.00 | $1,027 | $2,519 | 1.0× |
| 2020 | $74.00 | $1,014 | $2,092 | 1.0× |
green = beat the S&P 500 · red = lost money
Best entry point in our set: 2000, turning $1,000 into $3,750. 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. CVS is one of 258 positions on the wheel — including the ones that went to zero.
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