When the Chicago Cubs paid $155 million to bring left-handed starting pitcher Jon Lester to their team in the offseason prior to 2015, many theorized they added him simply to have an ace who they could feel good sending to the mound in a big game in the playoffs. So far, Lester hasn’t disappointed. In Game 5 of the 216 World Series, he did it again, leading the Cubs to a victory — and extending their chances of a drought–breaking championship win. He contributed his best in Game 7, and the rest is history. Here are the five best performances of Lester’s playoff career.
1. ALDS Game 4 vs. Los Angeles Angels (2008)
The wild–card Boston Red Sox accepted their underdog status when they went into their 2008 ALDS matchup with the Los Angeles Angels. The Angels boasted the best record in baseball that year. While Boston just won the World Series the season prior, they weren’t able to finish ahead of the Tampa Bay Rays in the AL East. The series sat at a critical point; Lester had just won in Los Angeles and Boston led the series, 2-1. They had a final game at home before a potential deciding game on the road.
But Lester didn’t let it get to the fifth game. Facing off against his future teammate and friend John Lackey — who is no stranger to winning big playoff games — Lester tossed an absolute gem. He held the high-powered Angels’ offense scoreless through seven innings, allowing four hits and two walks while striking out four batters. The Red Sox got two runs off Lackey, who pitched seven innings of his own. Boston won the game, 3-2, and moved on to the ALCS to face the Rays.
2. NLDS Game 1 vs. San Francisco Giants (2016)
The Cubs went 103-58 this season as the favorites in the National League. But this also created heavy expectations. Chicago opened the NLDS against the wild-card San Francisco Giants, who were just 87-75 during the season but won three of the last five World Series. Lester went to the mound for the Cubs, but the Giants’ Johnny Cueto countered him; he is no slouch on the mound, either.
Both pitchers threw well on a cool night at Wrigley Field that featured a strong wind blowing in from left field. Lester struck out five batters, allowing five hits and no walks in eight innings. He needed just 77 pitches, and probably would’ve come out for the ninth inning as well had Javier Baez not taken Cueto deep in the bottom of the eighth. The Cubs sent closer Aroldis Chapman out to save the game, topping off one of the finest performances of Lester’s career.
3. World Series Game 4 at Colorado Rockies (2007)
The first ever playoff start for Jon Lester was a big one. In the 2007 World Series, the Red Sox faced the Colorado Rockies — but it had been no contest at this point. Boston led the series, 3-0. Colorado hosted Game 4 at home, and the Red Sox turned to their rookie left-hander to give them a start against right-handed starter Aaron Cook of the Rockies.
Lester didn’t go deep into the game, pitching just 5 2/3 innings. But he held the Rockies scoreless, allowing just three hits and three walks with three strikeouts. It might not be the sexiest stat line, but for a 22-year-old kid in his first playoff start, it was huge. The Red Sox bullpen nearly gave up the game, allowing three runs. However, the Sox squeaked out a 4-3 victory and lift the World Series trophy for the second time in four seasons.
4. World Series Game 1 vs. St. Louis Cardinals (2013)
Lester’s second World Series start was a big one, too. In 2013, Lester and the Red Sox faced the St. Louis Cardinals, and he drew the assignment in Game 1. Cardinals ace Adam Wainwright was opposing him. The Red Sox knew it would be important to the rest of the series that they get off to a good start. Lester would be sure that they would.
Boston knocked Wainwright and the Cardinals’ bullpen around, scoring eight runs on eight hits — and three big fielding errors by St. Louis. Lester, on the other hand, was cruising. He struck out eight batters in 7 2/3 innings, allowing just five hits and a walk with zero earned runs. The Red Sox took the first game of the series, 8-1, and were well on their way to their third World Series title in the last 10 years.
5. World Series Game 5 at St. Louis Cardinals (2013)
The biggest game of Lester’s postseason career came just five days after his Game 1 victory in 2013. The Red Sox lost Games 2 and 3 to the Cardinals before coming back to win the fourth game and tie the series. That made Game 5 extremely critical to both teams, as the winner could close out the series in Boston two nights later. Lester’s task wasn’t easy, as he faced Wainwright yet again; he was determined not to have a second bad start against Boston.
Wainwright held the Red Sox down for the majority of the game, allowing just one run through the first six innings. But in the top of the seventh, he gave up a big ground-rule double to catcher David Ross that pushed across the go-ahead run. Lester, on the other hand, had ice-water in his veins. He threw 7 2/3 innings, striking out seven batters and allowing just one earned run on four hits. The Red Sox closed out the 3-1 win that night, and won the series with John Lackey on the mound in Game 6.