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(Jason Mark Anderman illustrates the logistics problem well in this comment to a backdating post on Ken Adams’s blog.) There’s nothing inherently illegal or unethical about backdating contracts, although backdating can certainly be both unethical and illegal, depending on the situation.
If someone presents you with a spreadsheet of the last month's stock prices and asks you to pick the date on which you want to pretend that you granted, or were granted, several million options, might that not at least spur further inquiry?
When then-general counsel Nancy Heinen emailed Apple (AAPL) CEO Steve Jobs such a spreadsheet on January 30, 2001, she noted that it was a bad idea to choose January 2 as the grant date--even though that was the day the stock had been at its lowest--if they wanted "to avoid any perception that the Board was acting in appropriately [sic] for insiders prior to Macworld announcements." (They ultimately chose one of the next-best dates from after Macworld.) Now isn't it obvious to everyone on that email that shareholders are being misled?
For more information on batches, read Managing automatic batches from the Staff site.
In the context of mutual funds, a feature allowing fundholders to use an earlier date on a letter of intent to invest in a mutual fund in exchange for a reduced sales charge, e.g.
She's saying that shareholders will naively think that the options were really granted on January 2, leaving them suspicious of springloading.