Five times teams had a sure win in their grasp, but just dropped the ball

Losing a game on a dropped pop fly in the 13th inning on a school (or work) night, as the Mets did in a 2-1 loss to the Giants on Monday, is high tragedy. 
But, what is comedy but tragedy plus time? Let's go back in time to similar ballgames where the pain isn't so fresh and where we, hopefully, can look back and laugh. 
Here are some other memorable moments when a game was lost on a dropped popup. 
Brant Brown gets the call of a lifetime
The 1998 Cubs ended up winning the National League Wild Card by one game over the Giants. Had they failed to do so, the name Brant Brown might be as well known as Fred Merkel and Steve Bartman.
Brought on as a defensive replacement for Glenallen Hill in the 8th inning against the Brewers on Sept. 23, 1998, Brown was there to catch what should have been the game-ending out on Geoff Jenkins lofted fly ball. Unfortunately, he dropped it and three runs came around to score. 

Even more famous than the drop was Ron Santo's call -- a guttural scream of "oh no!" that every Cubs fan at home could feel. You can listen to it here. 
Luis Castillo's dropped ball
Unfortunately for Castillo, this is the gold standard of game-losing errors. It had everything, including the backdrop of a Subway Series and Alex Rodriguez. With runners on first and second in the bottom of the ninth on June 12, 2009, Francisco Rodriguez got A-Rod to hit a popup to shallow right field. 
A moment later, K-Rod could only hold his hands over his head in disbelief: 

Russell Martin's winner
The best part of these plays is listening to the announcers as they prepare to call an easy out before launching into hysterics. "Looks like we're going to extra innings," Greg Brown intoned in the clip below before his voice jumped about 40 decibels in volume as the Pirates defeated the Astros, 5-4, on May 17, 2013. "Oh no! The Pirates win it! The Bucs win it! They [The Astros] dropped the ball!"  

The slip
Bases loaded, bottom of the 12th... what could go wrong? How about the very earth beneath your feet betraying you? Gregory Polanco had to suffer that indignity against the Cubs on May 15, 2015, and, perhaps even worse, was how his stumble to the ground resembled a piece of new-age dance. 

The infield fly
While some of these plays featured infielders, they all happened in the outfield. That was not the case on April 7 of this year when the Astros and Padres faced off. With a 3-2 count in the bottom of the 10th of a 0-0 game, Alex Bregman popped a ball up on the infield. Three infielders converged, but the ball chose the route less taken. Namely, the sweet grass. What a way for the game's only run to score.