Chicago Cubs: Ranking Jon Lester's biggest starts

2 of 7

(Photo by Jonathan Daniel/Getty Images) /

Jon Lester has had a lot of big moments since joining the Chicago Cubs. Here are five of his biggest starts since coming over in 2015.

At the end of the 2014 season, the Chicago Cubs were three years into their rebuild under Theo Epstein. The team was drafting many quality young players while also making trades to help slowly build the major league roster. The 2014-2015 offseason was pivotal, as the team hired Joe Maddon to be the manager to take this team to the next level after five straight losing seasons.

On the field, the team needed to sign a big-name free agent to take a giant step forward in their rebuilding process. Left-handed pitcher Jon Lester made sense, as he was one of the best pitchers in the game and had also proven himself in big moments. Maddon called Lester “Plan A” when it came to the team’s offseason plans.

Lester had spent his entire career with the Boston Red Sox, which included two World Series championships, before being traded to the Oakland Athletics during the 2014 season. When he became a free agent, several teams pursued, including the Cubs, Red Sox, San Francisco Giants, and Los Angeles Dodgers. Lester narrowed it down to the Cubs and Red Sox, and in the end, he went with the North Siders, signing a six-year, $155 million deal.

Lester has turned out to be arguably the most important free-agent signing in team history. The Cubs won a World Series and have made four straight playoff appearances since Lester joined the team, and he’s been an essential part of all of it. Many times, he’s come through in big situations. Here we’ll look at five of his most important starts in a Cubs uniform.

(Photo by Jared Wickerham/Getty Images) /

No. 5: September 15, 2015, Chicago Cubs at Pittsburgh Pirates

It was games like these for which the Chicago Cubs had signed Jon Lester: To be the stopper when the team was bleeding. Though they were in command of the second National League Wild Card spot at the time, the team had lost three in a row, including the first game of this doubleheader. The Cubs still had a chance to catch the division-rival Pirates for the first Wild Card spot, but they had to win this game if they had any chance of doing so.

In the first inning, Anthony Rizzo drove in Austin Jackson to make it 1-0 Cubs. It stayed that way until the fifth when the Cubs rallied for another run – an RBI double from Dexter Fowler – that was helped set up with a bunt from Lester. The Cubs had second and third with nobody out and the 2-3-4 hitters coming up, but they were unable to get any more runs across in that inning – or for the rest of the game.

Thankfully, that was all Lester needed. In the bottom of the seventh, the Pirates rallied to get runners on first and third with nobody out. On perhaps his most important pitch of the game, on a 3-1 count, he got Mike Morse to ground into a double play. A run scored, but that’s all the Pirates would get. After a scoreless eighth, Lester retired the side on just six pitches in the ninth to finish off his first complete game with the Cubs. His nine strikeouts were also a season-high.

As for the 2015 postseason, Lester would make two starts: one against St. Louis in the NLDS and one against the Mets in the NLCS. Both were Cubs losses.

(Photo by Dilip Vishwanat/Getty Images) /

No. 4: September 25, 2017, Chicago Cubs at St. Louis Cardinals

The 2017 season was not Jon Lester‘s best with the Chicago Cubs; his overall his 4.33 ERA, at the time, was his second-highest since his first full season in 2008. The team as a whole struggled for much of the season, which some attributed to a World Series hangover. And in his previous start before this game, Lester was coming off a rough outing in which he allowed seven runs in 4 1/3 innings against the Tampa Bay Rays.

Coming into this game, the Cubs were close to the division title and could do so on the home turf of their nearest competitor and rival, the St. Louis Cardinals. They would not be able to do it on this night, but they could get to within one game of doing so with their ace, Jon Lester, on the hill.

The Cubs would spot Lester a four-run lead in the first inning, then would add four more runs in the next two innings, and Lester did the rest on this night. He would allow a solo home run to Jedd Gyorko in the second inning, but that would be his only blemish over six innings of work. The bullpen would back Lester up, allowing just one run in three innings as the final score was 10-2. The Cubs would clinch the division two nights later in St. Louis.

Like in 2015, the Cubs were not successful in Lester’s 2017 postseason starts. The team lost all three of them, though he only allowed one run in each.

No. 3: San Francisco Giants at Chicago Cubs, October 7, 2016

Chicago Cubs fans were excited for the 2016 playoffs to start, but also must have been a little nervous heading into Game 1 of the National League Division Series. The team was coming off a dominant regular season in which they won 103 games and easily won their division. This might have been their best chance yet at a title. We would have hated to see it slip away in the first round of the playoffs against the Giants and all their “even year” magic.

That’s where Jon Lester comes in. He was coming off perhaps his best regular season yet and would finish second in NL Cy Young Award voting. Tonight, his task was simple, yet challenging: to outduel Giants ace, Johnny Cueto.

The game lived up to expectations and was as intense as an opening playoff game could be. Cueto shut down the Cubs for seven innings, but Lester matched each zero with one of his own. Finally, after Lester again put a zero up in the top of the eighth, Javier Baez came up to bat in the bottom half and hit a towering blast to left. It felt like the ball was in the air for about ten minutes before it finally landed in the basket, sending the Wrigley Field crowd into a frenzy and giving the Cubs a 1-0 lead.

Aroldis Chapman relieved Lester in the ninth and did what he was supposed to do: Put a zero on the board to seal the win. The Cubs would eliminate the Giants in four games in this series.

No. 2: Chicago Cubs at Los Angeles Dodgers, October 20, 2016

I chose this start – Game 5 of the National League Championship Series – over Game 1 for two reasons: First, the bullpens decided Game 1 and second, because I felt like the stakes were a little higher in this game. Jon Lester pitched well for the Chicago Cubs in both games, but in the end, I felt like this one was a little bigger.

More from Cubbies Crib

The Cubs would score first on an RBI double from Anthony Rizzo in the first inning, but the Dodgers would tie the game off Lester in the fourth on an RBI groundout from Adrian Gonzalez. It stayed that way until the top of the sixth when Addison Russell would hit a two-run home run to put the Cubs ahead 3-1.

Lester finished off seven innings of one-run ball, and then the offense would finish the job in the eighth, rallying for five runs, including a three-run double from Javier Baez. The Cubs would win the game, 8-4.

Again, I wouldn’t blame you if you felt like Lester’s Game 1 performance also deserved to be on this list: He allowed one run in six innings at Wrigley Field that night. He would have picked up the win had the bullpen not allowed two runs in the eighth inning, but thankfully the Cubs rallied for five in the bottom of the eighth to seal that game.

After this game, the Cubs would go home with a 3-2 series lead. However, unlike in 2003, there would be no drama this time, as the Cubs would win Game 6 by the score of 5-0 and clinch their first National League pennant in 71 years.

No. 1: Cleveland Indians at Chicago Cubs, October 30, 2016

The dream season was on the verge of ending, just short of that elusive championship. After the Cleveland Indians had won the previous night, they now held a 3-1 game lead in this World Series. The Chicago Cubs would be facing elimination for the first time all season. In Game 5, again, they would turn to their ace, Jon Lester.

The Indians would strike first against Lester in the second inning on a Jose Ramirez solo home run. It stayed 1-0 until the bottom of the fourth. I can still remember announcer John Smoltz saying that the Cubs had to score that inning; they had the middle of their lineup coming up, and the Indians’ shutdown bullpen awaited. Sure enough, the Cubs would rally for three, including a home run from Kris Bryant.

Lester would allow a run in the sixth but exited with the Cubs still holding the lead. Francisco Lindor singled in Rajai Davis in that inning, but for all the talk about Lester having trouble holding runners on base, the inning ended with the Cubs throwing out Lindor trying to steal second. Then, after Carl Edwards, Jr. got one out, Aroldis Chapman came in and got the final eight outs, shutting down the Indians and forcing a Game 6 in a tight 3-2 victory.

Cubs fans know the rest of the story: The team would go into Cleveland and win Games 6 and 7 to capture their first World Series title in 108 years. Along the way, we cannot forget the contributions of Jon Lester towards making that happen.

Will there be more great moments from Jon Lester with the Chicago Cubs?

As we can see, Lester has been part of a lot of big moments with the Chicago Cubs, and these were just five of them. Notably absent from this list is his appearance in Game 7 of the 2016 World Series, though I didn’t include that because it was a relief appearance and not a start. In picking these starts, my factors included the importance of the games, how well Lester pitched, and whether the Cubs won the game.

In the five years that Lester has been with the Cubs, we’ve seen him evolve and mature. Like many pitchers, he’s had to change and adapt his game as he’s gotten into his 30’s, and for the most part, he’s still been an effective pitcher.

We’ve also seen him grow as a hitter, as he’s had to bat regularly for the first time in his career as a National Leaguer. Indeed, he went 0-for-66 to start his hitting career before finally getting his first hit in 2016. Since then, he’s become a decent hitting pitcher.

In fact, we may one day look back at Lester’s tenure with the Cubs as the time in which he solidified himself as a Hall of Famer. He likely needs another good season or two to have a serious chance, but it is well within reach.

Next. Epstein's comments don't bode well for Cubs Maddon. dark

Unfortunately, Lester has struggled a bit this season; his 4.51 ERA would be his highest since 2012 and the second-highest since his first full season in 2008. However, if he can pitch well down the stretch this year and lead the Cubs deep into the playoffs, I’m sure fans will forget about his struggles from earlier this year.

So, do more memorable Lester moments await us? Let’s watch and find out!

Home / Chicago Cubs All-Time Lists

Chicago Cubs: Ranking Jon Lester’s biggest starts