Speaking with The Wall Street Journal, Cook said he was "surprised" to see the 8 percent drop in share price immediately following the release of Apple's quarterly results and wanted to pounce on the opportunity.
In a move he called "aggressive" and "opportunistic," Cook authorized the $14 billion repurchase, which brings the grand total to $40 billion worth of shares in the past year. To put that in perspective, Apple spent $16 billion on buybacks over a full quarter in 2013.
"It means that we are betting on Apple. It means that we are really confident on what we are doing and what we plan to do," Cook said. "We're not just saying that. We're showing that with our actions."
Apple announced in April 2013 a $100 billion capital return program that includes $60 billion in share repurchases and an increased quarterly dividend of 15 percent. The plan is scheduled to run through 2015.
Cook also offered insight into Apple's financial plans, saying the company purchased 21 companies over the past 15 months, with none of the deals exceeding $1 billion.
"You want to be able to adjust for the long-term interest of the shareholders, not for the short-term shareholder, not for the day trader," Cook explained. "We may see a huge company tomorrow that we want to acquire or something may happen in the stock market that's unpredictable."
Google, on the other hand, continues its buying spree with high-profile deals including robotics contractor Boston Dynamics and smart home device firm Nest. In the case of Nest, Google spent $3.2 billion to bring the company cofounded by former Apple employees Tony Fadell and Matt Rogers into the fold.
While Apple has yet to spend nearly that amount on a single buy, Cook said such an acquisition is not out of the realm of possibility.
"We've looked at big companies. We don't have a predisposition not to buy big companies," Cook said. "The money is also not burning a hole in our pocket where we say, 'let's make a list of 10 and pick the best one.' We have no problem spending ten figures for the right company, for the right fit that's in the best interest of Apple in the long-term. None. Zero."