With a runner on first and the score tied at 2 in the second inning at Wrigley Field, Clint Barmes hit a comebacker to Lester.
The ball got stuck in the webbing of Lester's glove. He took three steps toward first, couldn't get the ball loose, took a couple more steps toward first baseman Anthony Rizzo and flipped his glove with an underhand toss.
Rizzo dropped his glove and cradled Lester's mitt - with the ball still inside - for the out.
Lester has been criticized for his throwing trouble to first base on pickoffs. In his last start on Monday against the Reds, Lester threw a wild pickoff past Rizzo.