Anson spent most of his career with the Chicago Cubs franchise (then known as the "White Stockings" and later the "Colts"), serving as the club's manager, first baseman and, later in his tenure, minority owner. He led the team to five National League pennants in the 1880s. Anson was one of baseball's first great hitters, and was the first to tally over 3,000 career hits.
His contemporary influence and prestige are regarded by historians as playing a major role in establishing the racial segregation in professional baseball that persisted until the late 1940s. On several occasions, Anson refused to take the field when the opposing roster included black players.
After retiring as a player and leaving the Colts, Anson briefly managed the New York Giants. He ran several enterprises in Chicago, including opening a billiards and bowling hall and running a semi-professional baseball team he dubbed "Anson's Colts". Anson also toured extensively on the vaudeville circuit, performing monologues and songs. Many of his business ventures failed, resulting in Anson losing his ownership stake in the Colts (by then called the Cubs) and filing for bankruptcy.
Anson shares credit as an innovator of modern spring training along with then-Chicago President Albert Spalding, as they were among the first to send their clubs to warmer climes in the South to prepare for the season. On the field, Anson was the team's best hitter and run producer. In the 1880s, he won two batting titles (1881, 1888) and finished second four times (1880, 1882, 1886-87). During the same period, he led the league in RBIs seven times (1880-82, 1884-86, 1888). His best season was in 1881, when he led the league in batting (.399), OBP (.442), OPS (.952), hits (137), total bases (175), and RBIs (82). He also became the first player to hit three consecutive home runs, five homers in two games, and four doubles in a game, as well as being the first to perform two unassisted double plays in a game. He is one of only a few players to score six runs in a game, a feat accomplished on August 24, 1886.
Anson signed a ten-year contract in 1888 to manage the White Stockings (which, because of a typographical error he failed to spot, ended after the 1897 season instead of 1898), but his best years were behind him. He led the league in walks in 1890 and garnered his eighth and final RBI crown in , but declined precipitously thereafter. On the managerial front, he failed to win another pennant.
As the end of the 1880s approached, the club had begun trading away its stars in favor of young players, with the exception of the veteran Anson. Local newspapers had started to call the team "Anson's Colts", or just "Colts", before the decade was out. With the advent of the Players' League in 1890, what little talent the club still had was drained away, and the team nickname "Colts", though never official, became standard usage in the local media along with variants such as (Anson's) White Colts and (Anson's) Broncos.
He also mellowed enough that he became a fatherly figure and was often called "Pop". When he was fired as manager after the season, it also marked the end of his 27-year playing career. The following season, newspapers dubbed the Colts the "Orphans", as they had lost their "Pop".
Anson was well known to be a racist and refused to play in exhibition games versus dark-skinned players. This attitude was not considered to be unusual in his day, and Anson remained very popular in Chicago while playing for the White Stockings. On August 10, 1883 Anson refused to play an exhibition game against the Toledo Blue Stockings because their catcher, Moses Fleetwood Walker, was African American. When Blue Stockings Manager Charlie Morton told Anson the White Stockings would forfeit the gate receipts if they refused to play, Anson backed down. On July 14, 1887 the Chicago White Stockings played an exhibition game against the Newark Little Giants. African American George Stovey was listed in the Newark News as the Little Giants' scheduled starting pitcher. Anson objected, and Stovey did not pitch. Moreover, International League owners had voted 6-to-4 to exclude African-American players from future contracts. In September 1888 Chicago was at Syracuse for an exhibition game. Anson refused to start the game when he saw Walker’s name on the scorecard as catcher. Again, Anson pressured his opponents to find a Caucasian replacement.
In 1876, when Anson was playing for Philadelphia, Spalding and William Hulbert lured Anson to the Chicago team, which Spalding now managed. After signing the contract, Anson had second thoughts (his future wife did not want to leave her family in Philadelphia), and offered Spalding $1,000 to void the contract. Spalding held Anson to the contract, and Anson came to Chicago in March, 1876.
Spalding retired as a player and manager after the 1877 season, but continued as secretary, and later president, of the White Stockings. Anson became a player/manager of the team in 1879, and by 1889 had a 13% ownership.
In 1888 Spalding announced that the White Stockings, including Anson, and a "picked nine" from the rest of the National League would begin a World Tour after the end of the season. Spalding put up most of the money, but Anson invested $3,750 of his own. James Hart was hired as business manager and Anson developed an intense dislike for him.
After the Spalding stepped down as president of the Chicago club in 1891, he appointed James Hart to the position, which Anson felt should have been his despite his dismal business record. Spalding, however, continued to run the club behind the scenes.
In December 1892, Hart, with Spalding's blessing, reorganized the White Stockings into a stock company. Anson was required to sign a new contract, which ended in 1898 instead of 1899 as the previous one had. Anson spotted the error later but said nothing, trusting that Spalding would honor the previous terms.
Hart began to undermine Anson's managerial decisions by reversing fines and suspensions imposed by Anson. By 1897 Anson had little control over his players; after Anson demanded a sportswriter print that Anson thought \"the Chicago ball club is composed of drunkards and loafers who are throwing him down\", his days as manager were numbered. Spalding invited Anson and his wife on a four week journey to England in late November 1897. Spalding dropped many hints on the voyage, encouraging Anson to voluntarily retire, but Anson had no intention of doing so. Things remained in limbo until January 29 1898 when the Associated Press printed a statement by Spalding: \"I have taken pains as a mediator to find out from Chicagoans how they feel about a change of management. There has been a decided undercurrent in favor... Lovers of baseball think that Anson has been in power too long.\"
When the first edition of Macmillan's Baseball Encyclopedia was published in 1969, it disregarded a rule in place only for the season which counted base-on-balls (walks) as hits and times-at-bat instead of 0's in both categories as they were before and have been since. Anson's 60 walks were removed from his 1887 hit total, resulting in a career mark of 2,995.
The other controversy over Anson's total hits had to do with his five years in the National Association. Neither the Macmillan Encyclopedia editions nor Major League Baseball itself at that time recognized the NA as being a true major league. Only recently has Major League Baseball accepted the NA as a de facto major league; the MLB.com website now includes the NA years in Anson's record, placing major league hits total as 3,418. Anson is officially placed at seventh in the all-time leaders in hits.
Other sources credit Anson with a different number of hits, largely because scoring and record keeping was haphazard in baseball until well into the 20th century. Beginning with the publication of the Baseball Encyclopedia, statisticians have continually found errors and have adjusted career totals accordingly. According to the Sporting News baseball record book, which does not take NA statistics into account, Anson had 3,012 hits over his career. The National Baseball Hall of Fame (which uses statistics verified by the Elias Sports Bureau) credits Anson with 3,081 hits. This figure disregards games played in the NA, but includes the walks earned during 1887 as hits.
After a number of failed business attempts, including a handball arena and bottled ginger beer that exploded on store shelves, he was later elected city clerk of Chicago in 1905 and then, after serving one term, failed in the Democratic primary to become sheriff in 1907.
In 1907, Anson made another attempt to come back to baseball, acquiring a semi-pro team in the Chicago City League, which he would call "Anson's Colts". Anson initially had no intention of playing for the team, but in June 1907, at the age of 55, Anson started playing some games at first base in an attempt to boost poor attendance. Despite the draw of seeing Anson play, the team did not attract much attendance, and lost money for Anson. In the fall of 1908, Anson assembled a semi-pro football team, also called Anson's Colts. Although the football team won the city championship, they were not a financial success.
Some of Anson's few successful ventures were a combination billiards hall and a bowling alley he opened in downtown Chicago in 1899. Anson was named vice-president of the American Bowling Congress in 1903, and led a team to the five-man national championship in 1904. Anson was forced to sell the billiards hall in 1909 when faced with mounting financial problems that led to his bankruptcy. Anson was also an avid golfer.
With the aid of ghostwriter Richard Cary Jr., Anson's memoirs, titled A Ball Player's Career: Being the Personal Reminiscences of Adrian C. Anson, were published in 1900. This book is considered the first baseball autobiography.
Anson began acting during his baseball career. In 1888, he made his stage debut with a single appearance in Hoyt's play A Parlor Match at the Theatre Comique in Harlem. He also played himself in an 1895 Broadway play called The Runaway Colt, written to take advantage of his fame. Later, Anson began touring on the vaudeville circuit, a common practice for athletes of the time, which lasted up until about a year before his death. He first appeared in vaudeville in 1913 doing a monologue and a short dance. In 1914, George M. Cohan wrote a monologue for him, and in 1917, Cohan, with Chicago Tribune sportswriter Ring Lardner wrote another piece for him, titled First Aid for Father. Anson appeared with two of his grown daughters, Adele and Dorothy, and would bat papier-mâché baseballs made by Albert Spalding into the audience. He appeared in 1921 accompanied by his two daughters in an act written by Ring Lardner with songs by Herman Timberg.
Anson retired from vaudeville in 1921, and continued to refuse a pension from Major League Baseball, despite having no other income. In April 1922, he became the general manager of a new golf club in the South Side of Chicago. Following a glandular ailment, Anson died on April 14 at the age of 69 in Chicago, Illinois and was interred at the Oak Woods Cemetery in Chicago.
Anson was inducted into the Baseball Hall of Fame in 1939, one of the first 19th century players selected. Over 100 years after his retirement, he still holds several Cubs franchise records, including most career RBI, runs, hits, singles, and doubles. Defensively, he also holds the franchise record for putouts, but also is second in franchise history for errors.
The Ansons had seven children, three of whom would die in infancy. Daughter Grace was born in October 1877, son Adrian Hulbert was born in 1882 and died four days later, daughter Adele was born in April 1884, son Adrian Constantine Jr. was born in 1887 and died four months later, daughter Dorothy was born in 1889, son John Henry was born in 1892 and died four days later, and daughter Virginia Jeanette was born in 1899.