No one loves a good debate quite like baseball fans, and with that in mind, we asked each of our beat reporters to rank the top five players by position in the history of their franchise, based on their career while playing for that club. These rankings are for fun and debate purposes only.
Here is Jordan Bastian's ranking of the top five left-handed starters in Cubs history. Next week: Relievers.
1) Hippo Vaughn, 1913-21
Key fact: Most WAR (39.7) by a lefty in Cubs history
Lew Richie had a decent run with the Cubs for a few seasons in the wake of the franchise's back-to-back World Series crowns more than a century ago. He topped 15 wins twice and kept his career ERA under 3.00 across parts of the 1910-13 campaigns.
On Aug. 9, 1913, though, Chicago shipped Richie to Kansas City of the American Association and took a chance on a young lefty named Hippo Vaughn. He'd had mixed results with the New York Highlanders and Washington Senators in the American League, but grew into an all-time ace with the Cubs.
The 1.45 ERA that Vaughn spun over seven appearances down the stretch in 1913 was a taste of what would come over the next nine years.
There has been nearly 100 years of Cubs baseball since Vaughn threw his final pitch, but he remains the team's all-time leader in WAR, wins (151), starts (270), complete games (177), strikeouts (1,138) and innings (2,216 1/3) for a left-handed starter. He was especially dominant over the 1914-19 seasons, going 124-77 with a 2.10 ERA and an average of 292 innings per year.
Vaughn captured the pitching triple crown (ERA, wins and strikeouts) in the National League in 1918, when he won 22 games, struck out 148 and turned in a tidy 1.74 ERA. He topped 20 wins five times and did all he could to help the Cubs in the 1918 World Series.
During that '18 Fall Classic against the Red Sox, Vaughn logged three complete games with a 1.00 ERA, but was saddled with two losses. He was outdueled by Babe Ruth in a 1-0 loss in Game 1 and then lost Game 3, 2-1, opposite Carl Mays. He won Game 5 against Sad Sam Jones with a shutout, but Boston took the Series in six games.
Vaughn is also famous for being a part of a "double no-hitter" with Cincinnati's Fred Toney on May 2, 1917. In that contest at Chicago's Weeghman Park (Wrigley Field's original name), neither Vaughn nor Toney relinquished a hit for the game's first nine innings. The Reds finally broke through for one run on two hits in the 10th against Vaughn, and then Toney completed his 10-inning no-hitter.
2) Jon Lester, 2015-present
Key fact: 2.44 ERA in 12 playoff games for the Cubs
There are other lefty starters in Cubs history who rank higher than Jon Lester in a range of statistical categories. One could argue, however, that Chicago's signing of Lester prior to the 2015 season marked one of the most important turning points in the franchise's history. That is what propels him to No. 2 on this list.
Consider what Cubs president of baseball operations Theo Epstein said about signing Lester to a six-year, $155 million free-agent pact in December 2014:
"This signing really marks a transition of sorts for the Cubs, the start of a period where we are clearly very serious about bringing a World Series to the Cubs and the people of Chicago."
Given the leadership behind the scenes, the production on the field and the fact that the Cubs did indeed end their 108-year World Series drought with the triumph in 2016, Lester has been worth every penny of that pact to date.
Since joining Chicago, Lester has gone 74-41 with a 3.54 ERA in 159 starts. He has made two All-Star teams and was the runner-up for the NL Cy Young Award in 2016, when he went 19-5 with a 2.44 ERA. And none of that includes his work on the October stage for the Cubs.
Lester has taken the ball in five Game 1s in the playoffs for the Cubs, plus one Wild Card Game start. He was the co-MVP (with Javier Báez) of the 2016 NL Championship Series after turning in a 1.38 ERA in two starts, and then pitched in three of the seven games in the '16 World Series. That included winning Game 5 and picking up three relief innings in Game 7.
Among all the lefty starters in Cubs history, Lester ranks 13th in total WAR (13.4), seventh in starts and fifth in wins. Lester's 898 strikeouts are the fourth-most by a lefty starter in Cubs history, but his 3.27 strikeout-to-walk ratio is the highest among the 12 southpaw starters in team history with at least 700 innings.
3) Ken Holtzman, 1965-71, '78-79
Key fact: Threw two no-hitters
On Aug. 19, 1969, Braves slugger Hank Aaron drilled a pitch to the right of second base, where Cubs second baseman Glenn Beckert was stationed. He scooped it up and, following a brief moment to get a grip on the ball, fired to first baseman Ernie Banks for the game's final out.
Ken Holtzman had completed a no-hitter, and one of just three in baseball history with zero strikeouts.
"It was one of those days where fate smiles on you," Holtzman told Carrie Muskat in her book, Banks to Sandberg to Grace: Five Decades of Love and Frustration with the Chicago Cubs. "Aaron grounded out to Beckert to end the game. He was so nervous, he almost couldn't throw the ball to first base. He told me that for the next 30 years."
Then in 1971, Holtzman reached on an error in the third inning of a June 3 tilt against the Reds. Two batters later, Beckert came through for the pitcher again, connecting for an RBI single that held up as the difference in a 1-0 victory. Holtzman finished off that second career no-no with a strikeout of Lee May.
The Cubs took Holtzman in the fourth round of the first MLB Draft in 1965, and he developed into one of the great lefties in team history. Holtzman's 16.3 WAR ranks fifth all-time among Cubs left-handed starters, and he ranks third in starts (209), fourth in wins (80) and innings (1,447) and second in strikeouts (988) in that group in team history.
Holtzman was a part of the beloved '69 Cubs team that collapsed and was traded to the A's (for Rick Monday) before the '72 season. With Oakland, the lefty won three World Series rings, but he eventually returned to Chicago to close out his 15-year career.
4) Larry French, 1935-41
Key fact: Second-most WAR (21.8) in Cubs history among lefty starters.
Among the left-handed starters in Cubs history, only Vaughn compiled more WAR (via Baseball Reference) than Larry French did in his seven years with Chicago. He ranks second in that group in complete games (87), fourth in starts (185), second in wins (95) and third in innings (1,486).
French pitched in two World Series for the Cubs (1935 and '38) and was an All-Star in '40. He topped 15 wins four times for the Cubs and ended with a 3.54 ERA in 272 appearances.
5) Jack Pfiester, 1906-11
Key fact: Posted 1.59 ERA across the 1906-08 seasons
Almost no Cubs list is complete without someone representing the era in which the Cubs reached the World Series four times in five years (1906-10). Jack Pfiester was a big part of the Chicago staffs that helped win the 1907-08 Fall Classics, and he posted a stellar 1.85 ERA with 70 wins and 72 complete games in his career with the club.
In 1907, Pfiester led the Majors with a 1.15 ERA and he turned in a complete-game victory in Game 2 of that fall's World Series win over Detroit.
Dick Ellsworth (20.3 WAR across 1958, '60-66) or Johnny Schmitz (17.6 WAR from 1941-42, '46-51) could have easily cracked the top five on this list. Jake Weimer (15.2 WAR from 1903-05), Ted Lilly (15.1 WAR from 2007-10) and Paul Minner (14.6 WAR from 1950-56) are among other lefty starters from Cubs history also worthy of mention.