Despite reports of a dead deal, Wall Street's rumor mill never quite let go of the possibility of a mega merger between the two giant software makers, even until late last year.
It also didn't help that Benioff gave a somewhat odd answer to CNBC Jim Cramer's question about a potential deal last month, when he failed to outright deny the notion of selling.
But Microsoft's $26 billion deal for LinkedIn on Monday should finally put a nail in the coffin for any Microsoft-Salesforce acquisition rumors, at least for now.
The sheer cost of the deal, which is the largest in Microsoft's history, is one thing. But the work process involved in combining the two organizations should make it almost impossible for the Redmond company to even consider another mega deal with a company of the size of Salesforce anytime soon.
"Microsoft is going to have its hands full with the LinkedIn acquisition for the time being. I think it lowers any probability of a Salesforce acquisition for the time being," Wedbush Securities analyst Steve Koenig told Business Insider.
Salesforce now seems more focused on achieving growth through its own set of acquisitions. Earlier this month, it announced the biggest deal in history, acquiring Demandware for $2.8 billion. It's also picked up its pace of acquisitions over the past 6 months, already outpacing the number of companies it bought over the two previous years.
Friends but enemies
Despite the bromance between Salesforce and Microsoft that developed over the past year, it's hard not to notice the tension that seems to be building up between the two companies lately.
In fact, Microsoft CEO Satya Nadella's comments following the LinkedIn deal suggest that he wants to go after the
"This is really all about expanding the opportunity we have, going beyond productivity and collaboration tools to having a professional network," Nadella told Business Insider's Matt Rosoff, adding it helps target "sales professionals, talent people, and recruiting folks, as well as marketeers who are looking for B2B marketing targeting."
On top of that, there has been reports of competition between Salesforce and Microsoft intensifying after talks of a deal fizzed out, with Microsoft not being too cooperative when it comes to integrating the two products.
Plus, Benioff's narrative has noticeably shifted away from Microsoft in recent quarters. Last year, Benioff touted his newly found friendship with Microsoft in almost every public event, culminating in Nadella's keynote speech at Dreamforce, the first by a Microsoft CEO.
But in the most recent earnings call, Benioff was all over Amazon and its CEO Jeff Bezos instead, failing to make a single mention of Microsoft at all. The fact that Salesforce announced a big partnership deal with Amazon Web Services over Microsoft Azure also doesn't play too well in their partnership, either.
In any case, it's safe to bet that M&A in the software space will continue to heat up. This year is already shaping up to the best most active M&A market in years, and many Wall Street analysts expect the M&A frenzy to only intensify for the rest of the year.