In November 2016, Allergan CEO Brent Saunders announced that he had bought $1 million worth of his company's stock, and since then, the pharma giant's shares have rallied almost 27 percent.
Earlier that year, JPMorgan CEO Jamie Dimon made an even larger purchase in the face of a potential Clinton victory and no interest rate hikes in sight. He bought $26.6 million of his company's shares, and when that news broke, the stock jumped more than 8 percent in one day.
Same went for the CEOs of Restoration Hardware and Wynn Resorts, both of whose buybacks led to months-long rallies in their companies' stocks.
But Musk's and Dorsey's buybacks might be different, Cramer argued.
"I am concerned that Dorsey's a rich part-time CEO. He is also the CEO of Square, which is really pretty ridiculous when you consider how poorly Twitter is performing. Maybe his buy is much ado about nothing," Cramer said.
As for the CEO of Tesla, the move is more sound than Dorsey's, but Musk tends to be a showman, according to Cramer.
"Let's put it this way: neither man needed to buy," Cramer said. "But with both, I want to wait and see because neither company's making money and there's a lot more that could go wrong with these two companies than the others we have gone over."
Questions for Cramer?
Call Cramer: 1-800-743-CNBC
Want to take a deep dive into Cramer's world? Hit him up!
Mad Money Twitter - Jim Cramer Twitter - Facebook - Instagram - Vine
Questions, comments, suggestions for the "Mad Money" website? firstname.lastname@example.org