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But since then, all four major contenders — Apple, Amazon, Alphabet and Microsoft — have lost traction, particularly during the sell-offs U.S. stocks endured in the fourth quarter of 2018. In those three months, Apple's stock lost 30 percent of its value, Amazon's shed 25 percent, Alphabet's fell 13 percent and Microsoft's sank 11 percent.
"This time, ... the odds are very different," Cramer said on Thursday. "Now that many of these mega-cap tech stocks seem to have found a bottom here, I think it's time for us to start handicapping the race back to $1 trillion."
Apple, for one, re-entered the race in a less-than-ideal position, he said. Its last day as a trillion-dollar player was on Nov. 1, when the iPhone maker issued a disappointing forecast and announced a major change to its earnings reporting that some saw as a sign of slowing iPhone sales. On Jan. 2, Apple confirmed that it saw an iPhone slowdown in China.
Microsoft has also seen a change of fate, though its was notably positive. The stock had been trailing the other trillion-dollar contenders for most of 2018, but it held up in the marketwide declines, ending the year as the most valuable public company in the country.
Now, Amazon has retaken first place with an $810 billion market cap, Microsoft is a close second at $795 billion, Alphabet is in third place at $747 billion and Apple is trailing the pack at $730 billion.
And this time, "I think Amazon is the odds-on favorite, and not just because it's already in the lead," Cramer said.
The "Mad Money" host favored Amazon for several reasons: its stock still ended 2018 up 28 percent, which Cramer called a "pretty pedestrian" result for the e-commerce giant. Amazon is also finally seeing earnings growth after years of earnings losses coupled with revenue expansion, a common model for growing tech companies.
Lastly, its three businesses — the cloud-based Amazon Web Services, the advertising business and the consumer-facing retail segment — look to be performing strongly, which may be confirmed in its January earnings report.
Even so, "Microsoft is a real challenger" in the race, Cramer argued. Its Azure cloud services product is second only to Amazon, it has invested in growth with its LinkedIn and GitHub acquisitions, and its stock, according to Cramer, is "the safest of the bunch."
Google parent Alphabet might also put up a fight as its advertising arm continues to outperform and its "moonshot businesses," particularly self-driving car project Waymo and life science research subsidiary Verily, gain steam, Cramer said.
Apple, unfortunately, will remain in the "penalty box" until Wall Street sees tangible earnings and sales improvement, he said.
"I don't think Apple will win the race back to a trillion, but I do think it represents incredible value here," the "Mad Money" host said. "Bottom line here? In the race back to a trillion, Amazon's the new favorite and the competition's not that close, although I think both Alphabet and Microsoft are absolutely worth buying here. As for Apple, I think it's being chronically underestimated, but we shall see."
Disclosure: Cramer's charitable trust owns shares of Apple, Amazon, Alphabet and Microsoft.