Chicago Cubs: 5 best all-time pitchers in franchise history

When you root for a team like the Chicago Cubs, one of the most interesting aspects of your fandom is the history. We’re talking about more than a century of statistics, stories and personalities that have entertained generations of fans.

There have been some illustrious names to suit up for the North Siders. So many, in fact, you almost have to find a way to break it down and make it a bit more digestible when you’re talking about the team’s all-time best.

For our purposes here, I’ve narrowed this list of the best pitchers in Cubs history down to just five names. These pitchers span different eras in franchise history and played in wildly varying conditions, but at the end of the day, they stand above the countless other arms to take the mound for the team.

Chicago Cubs Greatest All-Time Pitchers: No. 5 – Charlie Root

If a baseball fan knows the name Charlie Root, it’s probably not as one of the greatest pitchers in Cubs history. More likely, it’s because he was on the wrong end of Babe Ruth’s rumored “called shot” during the 1932 World Series.

But let me tell you. There was a whole lot more to Root’s career than that one moment that may or may not have even happened. This guy was a stud for the club for the better part of two decades, anchoring pitching staffs that reached four World Series during his career.

Root made his Cubs debut in 1926 as a 27-year-old, immediately making his presence felt, making 32 starts, eating 271 1/3 innings and working to a 2.82 ERA. Now, the right-hander was never a big strikeout guy (he averaged 4.1 strikeouts per nine during his 17-year career), but he kept the ball in the yard and his team in just about every game he started.

His best season came the very next year, when he won a league-best 26 games, making 36 starts and a dozen relief appearances for Chicago. He racked up a staggering 309 innings that year, finishing fourth in the MVP race. But to say that was the end of his accomplishments on the mound would be wildly inaccurate.

For the next 15 years, Root was a steady presence for the team. That’s not to say he was the best pitcher in the league by any means. But he accumulated over 3,100 innings in his Cubs career, in which he turned in a 3.60 ERA and 3.82 FIP. To this day, he remains the only pitcher in franchise history with more than 200 wins – just eclipsing the number with 201 in his time on the North Side.

Chicago Cubs Greatest All-Time Pitchers: No. 4 – Mordecai Brown

Modern-day Chicago Cubs fans may feel like they’ve just experienced the ‘Golden Era’ in team history, but I’m here to tell you that’s not the case.

The true ‘Golden Era’ came during the back half of the first decade in the 20th century, when the Cubs featured a pitching staff anchored by Mordecai Brown. ‘Three-Finger’ played a critical role in the team winning it all in both 1907 and 1908, which, of course, marked the last time Chicago won it all prior to 2016.

From 1904 to 1910, Brown put up numbers that we’ll never see again from a Chicago pitcher – or any pitcher for that matter. There’s a reason he’s one of the greatest Cubs hurlers of all-time: and that reason starts and stops with this stretch of his career.

During that stretch, the Nyesville, IN native amassed just under 2,000 innings of work – which works out to 275 frames annually. But it’s not just that he ate innings; he dominated them, with a 1.56 ERA and 2.09 FIP. He won 20 or more games every single year from 1906 to 1911, regularly checking in with a sub-1.000 WHIP for good measure.

His name litters the Cubs’ all-time pitching leaderboard. He ranks third in Baseball Reference WAR (48), second in ERA (1.80) and wins (188), first in WHIP (0.998), shutouts (48) and adjusted ERA (152+) and fifth in innings pitched (2,329). For obvious reasons, Brown is enshrined in Cooperstown and ranks not just as one of the best Cubs arms ever, but one of the best players to ever set foot on a ballfield. 

Chicago Cubs Greatest All-Time Pitchers: No. 3 – Bill Hutchison

When you’re digging into performances from guys before the Modern Era (generally considered to begin in 1900), it’s a whole different type of experience. Examining the work of Bill Hutchison is a prime example of what I’m talking about.

So how in the world does a guy who only pitched for Chicago for seven years clock in as the third-best pitcher in Cubs history? Well, let’s get right into it. Hutchison pitched for the team from 1889 to 1895 and averaged 432 innings annually. But if you want to look at his prime, you’ve really got to hone in on a three-year stretch from 1890 to 1892.

During that span, Wild Bill did the work of three or four modern-day starting pitchers, racking up 1,786 innings of work (an average of 595 per season) with a 2.76 ERA and 124 ERA+. He started 194 games during that time – and he finished 188 of them. That’s right, he threw a complete game in 96.9 percent of those starts.

Now for any of you who’ve read my work, you know I don’t put a lot of stock in evaluating pitchers using wins and losses. But Hutchison won 41, 44 and 36 games, respectively, in those three years, leading the league in not only victories, but games, starts, complete games, innings and batters faced, as well.

By 1893, that workload clearly started to take a toll (along with the mound being moved to 60 feet, six inches from its previous 55 feet, six inches) – and by 1895, his Chicago career was at its end. He came back in 1897 with St. Louis, but made just five starts before hanging up his spikes for good.

Chicago Cubs Greatest All-Time Pitchers: No. 1 – Fergie Jenkins

There are very, very few baseball fans in the Windy City who wouldn’t label Fergie Jenkins the best pitcher in Cubs history. Part of that is certainly the relative recentness of his accomplishments on the mound.

More from Cubbies Crib

• Cubs should keep close eye on non-tender candidate Cody Bellinger
• Cubs starting pitching has been thriving on the North Side
• Make no mistake: the Cubs are very much about power hitters
• Cubs are giving pitcher Javier Assad a deserved shot
• Cubs: It’s time to start thinking about potential September call-ups

With the exception of Reuschel, the other guys on this list came long before most of us (or our parents, etc.) were on this planet. So it makes sense that Jenkins comes to mind. But that shouldn’t take anything away from what he did on the mound for the Cubs during his career.

Chicago acquired Jenkins in the spring of 1966 – and although a lot of folks don’t think of this deal as one of the team’s best all-time trades, it’s certainly up there. In 1967, the Canadian-born right-hander earned the first of three All-Star nods in his career, winning 20 games en route to a runner-up finish in the NL Cy Young race.

That kicked off a six-year stretch where Jenkins won a minimum of 20 contests annually, averaging over 300 innings each year with a 2.77 FIP. In 1971, he captured the National League Cy Young honors, winning 24 games, dominating the voting and leading the league in wins, starts, complete games (30 in 39 starts) and a wild 7.11 strikeout-to-walk ratio.

To this day, Jenkins remains one of the most beloved Cubs players of all-time – and it has little to do with his amazing career. He’s one of the most personable, loving guys out there and he certainly holds a special place in a lot of fans hearts – and the top spot on this list.