Investors love tracking insider buying and insider selling by corporate executives. When corporate insiders sell shares of their company, it may be for myriad reasons: buying a house, tax purposes, charity, spending cash and so on. When a corporate executive buys shares, the reason is generally considered to be that they think the stock is undervalued.

24/7 Wall St. routinely tracks insider buying and insider selling by corporate executives. The sales by corporate insiders are frequent, and the purchases are generally kept in check with their finances. So what are investors supposed to think after the chairman of Chesapeake Energy Corp. (NYSE: CHK) made a purchase larger than most people will make in their entire lives?

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Archie W. Dunham, chairman of the board, was reported as having purchased 1 million shares of Chesapeake Energy’s common stock. While the filing was listed as being March 31, the transaction date for the purchases was listed as March 27, 2015. The average price (VWAP) was listed as $13.9793. Tuesday’s SEC filing said:

This transaction was executed in multiple trades at prices ranging from $13.915 to $14.05. The price reported above reflects the weighted average purchase price. The reporting person hereby undertakes to provide upon request to the SEC staff, the issuer or a security holder of the issuer, full information regarding the number of shares and prices at which the transaction was effected.

Dunham is now listed as beneficially owning some 2,635,270 Chesapeake shares. This purchase date was after Chesapeake announced its planned capital spending cuts as well.

What investors will notice here is that this was almost certainly meant to be strategic in its statement. Most insider buying does not come with a price tag of $13.979 million — nor does such buying come with such an even number of shares. Another issue that was recently brought up is that Chesapeake was shown to be one of the worst S&P 500 stocks of 2015 so far and that it has been worse than its peers on a relative performance basis. Chesapeake was also shown to be among the most heavily shorted NYSE stocks as well.

Activist investor Carl Icahn recently bought more shares of Chesapeake as well. Icahn’s average price was $14.15, so Archie Dunham slightly beat Icahn on the price level.

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Chesapeake shares closed up 1.3% at $14.16 on Tuesday, and shares were up almost 1% at $14.30 in the after-hours trading session after the insider filing was seen. The natural gas player has a market cap of $9.4 billion and a 52-week trading range of $13.38 to $25.92 per share.

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