Kobe Bryant always looked up to Michael Jordan. It doesn't take long into any Kobe Bryant highlight reel to see the obvious influence 'His Airness' had on Bryant's game. So it must've been absolutely crushing when his idol told him he could "never fill" his shoes.
On Episode 52 of the 'No Chill Podcast', former NBA guard Gilbert Arenas told a story from the 2002-03 season, in which Arenas was a teammate of Jordan, who was in the second season of his NBA comeback with the Washington Wizards.
Earlier in the season, Arenas stated that after a game MJ told a young Bryant—metaphorically speaking of course—that he could wear his shoes, but "never fill them".