The top-tier executives -- head of marketing Philip Schiller, general counsel Bruce Sewell and chief operations officer Jeff Williams -- each gained control of 525,000 shares on Monday.
At Monday's closing price, the shares were worth $55.6 million.
The shares were the second half of an award given in early November 2011, when Apple awarded 150,000 shares each to six men. Since then, Apple's shares split 7 for 1, making the original allotment 1,050,000 shares. Three of the six awardees are no longer with the company.
At the time, Apple granted "restricted share units," or RSUs, which were not given immediately, but instead were vested in two equal parts on June 21, 2013, and on Monday. Each executive had to remain with the company to collect those vested shares.
While the grant was worth a putative $59.8 million at the time it was awarded, the subsequent increase in Apple's stock price pushed the total considerably higher. At the time each half vested, the total value of the RSUs was worth $80 million to Schiller, Sewell and Williams.
Apple's grants to the executive team followed a much larger award given to CEO Tim Cook in August 2011, after he took the top spot when Jobs stepped down. The board of directors awarded Cook 1 million shares -- which with the split became 7 million shares -- that were to vest over a 10-year stretch.
Companies often award large stock grants to senior leaders to entice them to stay. It's not a foolproof way to retain executives, as companies often grant stock to incoming new executives to match what they lost when they left their previous employer, and their unvested shares on the figurative table.
Apple did just that when it hired Angela Ahrendts to become its head of retail and online sales, handing her about $37 million worth of shares to replace the equity she had accumulated as the CEO of luxury retailer Burberry before leaving for Apple.