Lets find out.
Wikipedia tells us:
- ESL was worth $3.1 billion in March 2012,
- ESL became CEO of Sears Holdings in January 2013,
- ESL was worth $2.2 billion in August 2016
What if ESL liquidated everything in 2012, and decided to spend the decade golfing?
First he'd pay the LTCG tax. Top Federal LTCG rate was 15% in 2012. Connecticut was 6.7%. NIIT is another 3.8%. Total tax haircut of 25.5%. Not all investments will get this hit, and if ESL had time and patience he would have reduced the tax hit. But lets just assume he sold everything all at once and got out of managing a hedge fund.
He'd then have $2.3 billion. Now what if he took that $2.3 billion and dumped it in an S&P 500?
The S&P 500 gained 56% between March 2012 and August 2016. Our man ESL would have $3.6 billion in net worth on August 2016, and a he-l of a golf swing. That's significantly more than what he was actually worth in August 2016.
The S&P 500 gained nearly 199% between March 2012 and May 2021. That's nearly $7 billion in net worth, placing him firmly in the top 100 richest Americans. Instead he doesn't even rank on the Forbes 400 now.
For another perspective: Drooling mo--ns bought shares of Hertz in an initial bankruptcy offering knowing full well that IT WAS BANKRUPT, and those drooling mo--ns made bank less than a year later. In this screwed up market where people with 0 IQ manage to make money hand over fist, it is all the more remarkable that ESL managed to burn through his wealth.
ESL was the worst thing to happen to Sears. ESL was the worst thing to happen to Kmart. Now we know that ESL was the worst thing to happen to ESL.