"Do you double down, betting something happens [that is] good, or do you ring the register, maybe take some profits here and now?" the "Mad Money" host asked.
To many investors, the latter may sound tempting, despite Whole Foods stock's 10 percent jump on the Jana news. Competitors like Wal-Mart and Kroger have encroached on he high-end grocery chain's turf by bringing cheaper organic and natural options to their shelves.
And although Whole Foods has tried to differentiate with its cost-saving 365 brand, array of prepared food options, and community service initiatives, Cramer argues that the brand cannot escape its too-expensive perception.
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"The legend of Whole Paycheck, with is image that only the rich can afford to go there, can't seem to be shaken," he said. "Cheaper is a word that's almost never associated with Whole Foods."
But Cramer also wonders if Jana, now Whole Foods' second-largest shareholder, can really make a difference in the company's prospects.
Not only does Cramer have little faith in Jana's directorial nominees, it has become clear to him that Jana is not just out to buy back shares of Whole Foods, a strategy that has not paid off much since company leaders announced it in 2015.
Jana's other initiatives could be to push executives to cut its overhead, boost sales, connect more with customers, or spend on better technology to improve point of sale and customer relations management.
Cramer, however, is concerned that Whole Foods' "wildly independent" CEO John Mackey will be reluctant to hand control over to a newcomer.
"If anything, he'll ignore Jana and just keep doing it his way," the "Mad Money" host said.
Cramer said the best hope for a turnaround — and Jana's possible next move — is "a foreign buyer who wants to take on German Trader Joe's."
While Jana could get bailed out if food inflation returns, if the activist fund does not have some interested overseas buyers up its sleeve, Cramer sees no way up for Whole Foods' stock.
"Only a sale can make this thing go higher," he said. "So unless Jana has a buyer lined up, I bet you're going to wish you sold Whole Foods if it somehow gets back to that vaunted $34, $35 level."
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