Jon Lester shares the 2016 World Series Game 5 memory Cubs fans will never forget

Jon Lester might be the highlight of the 2016 World Series Championship team celebration at Cubs Convention. Lester was named a Cubs Hall of Fame inductee for 2026 along with Jody Davis and the late Vince Lloyd. While this entire weekend will be spent reminiscing with various members of that squad, Lester was the first to do it on the Marquee network after the opening ceremony.

Jon Lester reflects on 2016 World Series Game 5 changed everything for Cubs history

Lester discussed his crucial game 5 start in the 2016 World Series with the Cubs down 3-1 in the series and their backs against the wall. He mentioned his opening warmups well before the game started, and how the Wrigley Field stands were already full. There was also a humorous quip about "demons" entering his head, and he stared down battery mate David Ross after the first inning was over (he struck out the side in order).

So why not further reminisce about that jaw-clenching game?

One could argue it's the start that cemented Lester into eternal Cubs lore. The team was one loss away from heading to year 109 without a title. Even if it felt like a small glimmer of hope, it wasn't over until it was over.

The Cubs entered the game having scored a total of two runs in two games at Wrigley Field in the series. They were beaten 1-0 in Game 3 and trounced 7-2 in Game 4, with all the momentum seemingly on Cleveland's side. The Cubs were hitting .204 in the series as a team, with Anthony Rizzo, Kris Bryant, and Javier Baez going a combined 3-21 (.143) in games 3 and 4. A spark needed to happen and fast.

Lester gave up a solo shot to Jose Ramirez in the top of the second, and the Indians could taste victory. However, the big lefty buckled down and kept them in the ballgame. The series-changing rally in the bottom of the fourth is one for the ages. Bryant's leadoff solo shot, followed by a Rizzo double, Ben Zobrist single, Addison Russell infield RBI single, Jason Heyward strikeout, Baez bunt single, and Ross sac fly is all the Cubs would need this game.

It was a nail-biter the rest of the way. Lester gave up one other run in the sixth on an RBI single by Francisco Lindor, but that was it. He went 6.0 innings, gave up two runs on four hits, and struck out five, walking none. After Carl Edwards Jr. got one out in the seventh, it was on to closer Aroldis Chapman for the eight-out save.

This was a workload Chapman was not used to carrying, and it's known that Joe Maddon probably overused him in the postseason. That night, it was necessary, being a one-run game and no tomorrow. In 2.2 innings, he gave up one hit, no runs, struck out four on 42 pitches, getting those final outs to send the series to Cleveland.

Game 5 is the only World Series win at Wrigley Field for the Cubs since the end of World War II, and that night was filled with Hollywood-like drama. While thousands of Cubs fans traveled to Cleveland for the final two games, the roar of 40K at Wrigley when that final out in Game 5 was made brought goosebumps to even the most casual fan. Hopefully, there will be another moment like that soon at Wrigley Field.