The Cubs’ 10 Greatest Pitchers

Mordecai “Three Finger” Brown (1904-12, 1916)

Tim Lincecum may have been known as The Freak, but it’s Brown—whose pitching hand was mangled in a childhood farming accident and, as a result of it, allowed him to develop a devastating curveball—who really deserves the nickname, as he confounded opponents for nearly a decade with the Cubs.

Brown was arguably second to none during the deadball era, winning 20-plus games over six straight years (1906-11), producing a 1.04 earned run average in 1906 that’s the lowest in modern NL history, and finishing his career with a 2.06 ERA that’s the majors’ third lowest since 1900. Furthermore, Brown won bragging rights over Christy Mathewson—his chief rival of the period—taking a 13-11 record in head-to-head matchups against the New York Giants ace.

The value of Brown’s workhorse ethic is best noted in that he not only was the perennial team leader in wins, but also in saves; in fact, he led the National League in the latter figure over four straight years, capped by a then-record 13 in 1911. Brown’s biggest career win came in relief, when he took over for an ineffective Jack Pfiester and stifled the Giants in the do-over, winner-take-all 1908 match (made possible by Fred Merkle’s baserunning gaffe in an earlier contest) that ended the regular season and gave the Cubs the NL pennant. The losing pitcher that day: Christy Mathewson.

Brown was let go by the Cubs after a subpar 1912 campaign but returned for a final, mostly ceremonial hurrah in 1916 at age 39; he finished his career with a 188-86 record for Chicago, adding five more wins in World Series action—two of which took place during the 1908 triumph over Detroit, resulting in the Cubs’ last championship for 108 years.

Pete Alexander (1918-26)

The Cubs snagged the league’s premier pitcher of the day from the Phillies, who feared that Alexander would be snagged away by the military for war duty during World War I. The Phillies were right, but any perception that they were shortsightedly ignoring the long term was proven serendipitously wrong when Alexander came back from the front shellshocked, partially deaf and epileptic—the latter condition leading to increased dependency with alcohol that would torment the rest of his life.

Still, the Alexander that pitched for the Cubs, while not the same, remained highly effective, even reprising his early Philadelphia dominance in 1920 with NL highs in wins (27), ERA (1.91) and innings (363.1); his sub-2.00 ERA was his fifth consecutive such number. Alexander’s superiority diminished afterward with ERA figures sustained over the 3.00 mark (owing in part to the hitting splurge of the 1920s), but he remained tough on opponents, who still found it tough to hit off him and very tough to walk on; at one juncture, he threw 52 straight innings without issuing a base on balls.

When a young and untried Joe McCarthy took over as the Cubs’ manager in 1926, the veteran in Alexander immediately challenged and clashed with him, hastening his departure from Chicago midway through the year to St. Louis, where he had a few golden moments left to experience.

Hippo Vaughn (1913-21)

After bouncing around the American League and then the minors for five years, Vaughn was given a chance by the Cubs—and immediately, he clicked, becoming the team’s workhorse throughout the 1910s by averaging close to 300 innings annually over a seven-year span.

Nicknamed Hippo for his bulky frame that grew larger as the years wore on, Vaughn was a five-time 20-game winner in Chicago and is best remembered for participating in the famous 1917 double no-hitter in which he and Cincinnati’s Fred Toney each threw hitless ball for nine innings, with Vaughn finally conceding offense in the 10th and losing, 1-0.

Vaughn’s best season undoubtedly took place a year later in 1918, when he won the NL ERA title with a 1.74 mark and also led the league in strikeouts and shutouts (with eight). He followed that up with three complete-game performances in the World Series against Boston, allowing just three earned runs in 27 innings—but lost two out of the three as the Cubs gave him little offensive support.

Following the 1920 season, Vaughn’s personal life unraveled as, among other things, he was slashed in the stomach by his father-in-law over a domestic dispute. His baseball career quickly followed suit, as Vaughn won just three of 14 decisions with a 6.05 ERA in 1921 before being let go by the Cubs. He forged on, logging time in the minors and semi-pro leagues all the way through the age of 49.

Charlie Root (1926-41)

Root will forever be known as the man who served up Babe Ruth’s “Called Shot” in the 1932 World Series, a home run he insists was never pre-ordained by Ruth; he said shortly before his death that had Ruth actually called the shot, he would have knocked the Yankee star on his butt with the next pitch rather than heave it down the middle.

Less famed about Root is that he’s the winningest pitcher in Cubs history, racking up 201 victories over a 16-year tenure in Chicago. His most prodigious effort came in 1927, when he led the majors with 26 wins (against 15 losses) and threw over 300 innings for the only time in his career. He was also a sharp 19-6 in 1929, and produced a career-low 2.60 ERA in 1933 during, curiously, his final year as a full-time starter for the Cubs. For the final eight years of his time in Chicago, Root relieved more often than not, often serving as the nearest thing to a closer for the Cubs.

Root’s biggest disappointment was that even though he appeared in four different World Series for the Cubs, he never won a game—finishing at 0-3 with a 6.75 ERA in six appearances, four of them as a starter.

Lon Warneke (1930-36, 1942-43, 1945)

In 1932 at age 22, Warneke burst onto the scene in his first full season for the Cubs by sporting a 22-6 record and the majors’ best ERA at 2.37 that earned him runner-up honors for the NL MVP. More success quickly followed; in 1934, on his way to his first of two 20-win campaigns, Warneke began the season with back-to-back one-hitters—the first of which came within two outs of being a no-hitter. Warneke was adept with the glove, setting a record (since broken) for most consecutive games played by a pitcher without committing an error.

When his record slipped to 16-13 in 1936, the Cubs sent him to St. Louis for Ripper Collins in a deal that worked out poorly for Chicago; although Warneke remained solid but never regained his early-career heights, Collins did a quick fadeout. Following a second, less successful stint with the Cubs during World War II, Warneke retired and took up umpiring, ultimately spending seven more years in the majors; in fact, he would become the only person to truthfully say he played and umpired in both the World Series and All-Star Game.

Bill Lee (1934-43, 1947)

Not to be confused with “Spaceman” Bill Lee of Boston Red Sox fame in the 1970s, the Cubs’ version of Lee was more down to earth and every bit as good, if not a little better—especially in his time in Chicago.

Lee was initially brought into Branch Rickey’s overstocked farm system in St. Louis, and was sent to the Cubs when the arrival of Dizzy and Daffy Dean clogged up his path to the Cardinal rotation. With Chicago, Lee twice won 20 games, and put together a career year in 1938 when he led the NL with 22 wins (against just nine defeats), a 2.66 ERA and nine shutouts; he also threw three scoreless innings at that year’s All-Star Game and, in the World Series against the Yankees, pitched well but lost both of his starts via a lack of support from his teammates. Lee’s career gradually came undone by failing eyesight, which ultimately led to blindness.

Claude Passeau (1939-47)

Never dominant but always reliable, Passeau was an underrated, winsome contributor for the Cubs, never finishing below .500 until his final campaign in 1947 when he played sparsely and with pain. The winning was a relief for Passeau, spurred to life in Chicago after spending his first three years of his career saddled with losing teams and high ERAs in Philadelphia with the then-woebegone Phillies.

Relying on a sinker that opponents often grumbled to be a spitter in disguise, Passeau did his best to help the Cubs take the 1945 World Series from the Detroit Tigers. He threw a one-hitter in Game Three to give the Cubs a 2-1 Series lead, but with four games to win two back at Wrigley Field, the Cubs could only win one—blowing a 5-2 lead in Game Six that Passeau had helped give them—and lost in seven games overall.

Jack Taylor (1898-1903, 1906-07)

An utter epitome of the deadball era, Taylor was equal parts durable and untrustworthy. He was also quite good. The right-hander came into his own after the turn of the century, producing a 23-11 record and leading the NL with eight shutouts and a 1.29 ERA in 1902 for a .500 Cubs team. His eventual fame within the record book had, however, started a year earlier when he began a record streak of 188 games in which he started—and completed. It’s one of the more impressive pitching achievements from the deadball era that’s considered eternally safe from being topped.

In 1903, Taylor won another 21 games, but it’s events at the end of that season that landed him on the trading block. During a postseason exhibition series with the crosstown White Sox, Taylor was rocked—and a suspicious Cubs front office believed he was laying down for extra cash from the opponent. Taylor himself confirmed it afterward when, following a trade to the St. Louis Cardinals, he blurted out: “Why should I win? I get $100 for winning and $500 for losing.” (The Cubs hardly regretted the trade; they got Three Finger Brown in return.)

Three years later, the Cubs—under new management and soaring in the NL standings—brought Taylor back in a midseason trade, fully aware that he had continued to be embroiled in game-fixing controversy back at St. Louis. Now in his mid-30s, Taylor played it straight and solid for his second go-around with the Cubs, winning 12 of 15 decisions with a 1.83 ERA, and lasted an additional year in Chicago before playing out the end of his career in the minors.

Ferguson Jenkins (1966-73, 1982-83)

Many would easily imagine Jenkins as the all-time Cubs leader in victories, yet the man who ultimately amassed 284 career wins totaled only 167 for Chicago—most of those coming during a prodigious seven-year stretch in which he won 20 or more games six straight times. He wasn’t particularly death upon hitters—he often led the league in extra base hits allowed and never won an ERA title—but he certainly had a knack to rack up wins.

As with Alexander and Passeau before him, a young Jenkins came to the Cubs (along with two other players) via a trade with the Phillies—a deal which sent veteran hurlers Larry Jackson and Bob Buhl, both at the tail ends of their careers, to Philadelphia. Needless to say, Jenkins gave the Cubs long-term benefits from the trade with eight years of workhorse effort—and a NL Cy Young Award in 1971 when he led the circuit with 24 wins. Jenkins was dealt to Texas after 1973 in another deal that benefitted the Cubs, receiving future perennial batting champion Bill Madlock; he returned to Chicago for a two-year encore at the end of his career, with fair results.

Greg Maddux (1986-92, 2004-06)

Wrigleyville missed out on calling one of the game’s great pitchers one of its own during his prime, but did get to cheer Maddux on as a budding talent who was closing in on peak form—and then again at the end of his career, as if making it up to Cubs fans.

Maddux’ first full year in Chicago was a certifiable bust, ending with a 6-14 record and a 5.61 ERA—but he became a changed man a year later, posting an 18-8 mark and 3.18 ERA; he lowered that figure to 2.95 in 1989 (with a 19-12 record) but tearfully failed the Cubs in the NLCS against the Giants, logging just 7.1 innings in two starts and allowing 12 runs. Maddux went from star to superstar in 1992, authoring a terrific 2.18 ERA and recording his first of (only) two 20-win seasons while winning his first of four Cy Young Awards. Unfortunately for the Cubs, his breakout to stardom occurred as he became a free agent; Atlanta scooped him up and he became unworldly throughout the rest of the 1990s for the Braves.

By the time he came back to Chicago at age 37, Maddux had long since lost his Hall-of-Fame luster but continued to show off his catlike reflexes on the mound that led him to win Gold Gloves in each of his three years back with the Cubs. He would ultimately total 18, the most by any major leaguer regardless of position.