Hindsight is 20/20 - we all wish we could have invested in GOOGL and AMZN in 1999, or basically any of the big tech giants of today (those that actually existed back then). Even investing across a number of equities by throwing darts at a board lined with ticker symbols during 'The Great Recession' would have paid off nicely as the markets have rebounded to new highs. Carl Icahn's investment in AAPL was an interesting one - a very wise move that proved to be quite successful, but it could have been far more lucrative if he had a little more patience with the tech giant, or perhaps he saw something that nobody else did. Now Warren Buffett is in AAPL - a most unusual investment for a man who loves businesses with stable growth and historic breadth (transports, industrials, etc.).

History

On August 13, 2013, legendary investor, Carl Icahn, sent a tweet stating that his firm, Icahn Enterprises, LP, had taken a large position in AAPL and that he believed the company was significantly undervalued.  Throughout August 2013 and May 2014, Icahn went on to acquire 52,760,000 shares of AAPL (post-split) with a cost basis of ~$3.74 billion ($70.84 per share). Icahn met with Cook and then CFO, Peter Oppenheimer, to engage them in discussions over upping the capital return program, which AAPL did. At one point, Icahn said that AAPL was worth $240 per share, which would equate to a market cap well north of $1 trillion. However, Icahn began unloading his AAPL position in December 2015 and at the end of 2015, had pared his position down to 45,760,000 shares.

Sour Fruit

In April-2016, after AAPL announced its first-ever iPhone unit decline in CQ1-2016 / FQ2-2016, Icahn acknowledged that he had unloaded his entire AAPL position. Icahn stated that he had concerns over the company's growth engine (China) and the potential for protectionist policies that would undermine AAPL's ability to compete in that market. Icahn stated that he made about $2 billion on the position. Based on my calculation, Icahn made roughly $1.7 billion (which includes both stock appreciation and dividends) - an extraordinary gain that any investor, on any level, would be happy with. 

However, since Icahn's disposition, AAPL has made quite an impressive run to all-time highs. Based on AAPL's closing yesterday (May 18th) at $152.54 per share, I believe Icahn left about $2.65 billion of gains had he held on to his entire original position of 52,760,000 shares. But who really knows? Perhaps Icahn was right and that this latest run is not indicative of the long-term trajectory of the company. Sometimes the ripest fruit turns out to go sour real fast, but I often wonder if he ever thinks about it.