In baseball’s infancy, a group of powerful owners brought order to Major League Baseball, elevating the game to prominence in American culture. They held all of the cards as players had little rights, especially in terms of salary. This was due to the state of the game at the time, but also to the lack of education among the players.

Shoeless Joe Jackson, perhaps the greatest pure hitter to ever play baseball, was illiterate. This made it necessary for his wife to read all of his contracts and decide if he should sign them. Following the fix of the 1919 World Series, the team was able to isolate Jackson away from his wife and secure a deal enabling the club to terminate the contract with only a ten-day notice.  

Jackson specifically asked about this right of termination, but due to his illiteracy, and without his wife to read the contract for him, the team told him such a proviso was not in this contract. Duped by management, Jackson signed the contract believing the clause had been removed. Jackson is only one example of the manner in which baseball owners treated their players in the early 20th century.

Things are much different in baseball today with a powerful players union and a collection of high-profile athletes who continuously want to exceed the contracts of their colleagues. While the way players were treated in the early 20th century seems a bit harsh, a few of these owners, some of which were well-known misers, helped transform baseball into America’s Pastime.

Charles Comiskey

Comiskey was the classic baseball owner in the early 1900s. A cheapskate who routinely used loopholes in player contracts to avoid paying what he owed them. This behavior caught up to him in 1919 when a handful of his players threw the World Series.

Eddie Cicotte was perhaps the saddest case among the group who needed the money to support his growing family. Cicotte was promised a bonus that season if he won thirty games, but Comiskey had him scratched from a couple of starts down the stretch to “keep him fresh” for the playoffs.

Those missed starts prevented Cicotte from winning 30 games and Comiskey refused to pay the bonus he desperately needed.

Cicotte had always been known as a devout Catholic, a good man who only wanted to provide for his family and live a good life. His participation in the fix was due to need, not greed.

Cicotte’s conscience ate at him over the next year, moving the knuckleballer to give a tear-filled confession to Comiskey at the end of the 1920 season.

Had Cicotte not confessed and named the other conspirators in the fix, the Black Sox scandal may have remained a secret to this day. But Cicotte couldn’t live with the guilt and shocked baseball with his confession.

The fix of the 1919 World Series became public knowledge and baseball faced its first scandal. The eight players believed to be involved were brought to trial for their offenses and subsequently acquitted, but other owners began demanding the game be cleaned up.

Baseball had used gamblers to help jumpstart the game, but the time of reckoning had come.

Kenesaw Landis was appointed as the first Commissioner of Major League Baseball in 1920 and immediately banned any player who fixed a game for gamblers, including the eight members of the White Sox connected with the fix.  

The creation of the commissioner’s office transferred power from the owners to an objective arbitrator and Comiskey was directly responsible.

Jacob Ruppert Jr.

Colonel Ruppert is best known for fleecing the cash-strapped Harry Frazee with his acquisition of Babe Ruth after the 1919 season. At the time the Red Sox were the talk of baseball and the lowly Yankees had been a middle-of-the-pack team at best. In fact, the cross town Giants routinely outdrew the Yankees in the early 1900s.

All of that became a distant memory once Ruth became the original Bronx Bomber.

Ruppert did little for the game overall, but he did deliver the Yankees to baseball and the sport would not be the same without them. During his tenure the Yankees rose from obscurity to become the most dominant organization in sports history.

Beginning with the purchase of Ruth’s contract, Ruppert guided the Yankees through the greatest 20-year stretch baseball has ever seen. They won their first World Series in 1923, besting the rival Giants in six games.

The 1927 Bronx Bombers are widely considered the best baseball team to ever jog across lines of chalk, a team Ruppert built around the rotund Rose and a young Lou Gehrig. Known for their ‘Murders Row’ lineup, the ’27 Yankees put on an offensive performance that would rival the powerhouses of the game today.

Before Ruppert’s death in 1939, the Yankees won ten American League pennants and seven World Championships.

The Yankee mystique was born.

George Steinbrenner

The Boss changed baseball in the late 1970s when free agency made its first appearance in baseball. Fans today are astonished by the way the Yankees spend hundreds of millions in payroll each season. Those in small markets cry for a salary cap to stop the Bombers from spending more than some small Latin American countries.  

Steinbrenner’s Yankees were a contender when free agency was established and he wasted little time signing players like Reggie Jackson to unprecedented contracts. He was the first to use free agency to augment his club and build a champion, a pioneer in the growth of greed among players.

Nolan Ryan became the first million dollar player in 1980, Kevin Brown the first to reach $100 million in 1999 and Alex Rodriguez exceeded $250 million in 2001. It’s a trend that will never stop as baseball has become a league where players constantly want to surpass the contracts of their colleagues. 

He revolutionized baseball with his marketing techniques and incited the television revenue battle between clubs with the creation of his own regional network in 1999. The Yankees can afford an annual payroll approaching $200 million because Steinbrenner built an empire and altered the way business is done in baseball forever.

Walter O’Malley and Horace Stoneham

In the mid-20th century, Major League Baseball was confined to a handful of teams in the northeast of the United States including three teams in New York City alone. Tired of playing second-fiddle to the Yankees, the Giants and Dodgers began looking for places to move their organizations.

O’Malley tried to secure a new stadium for his Dodgers, even playing some games in Jersey City to show the city he was serious. After his attempts became fruitless, O’Malley began to look west for a new home.

Stoneham faced similar circumstances with the Giants, trying to broker a new stadium deal or at least share Yankee Stadium with the team sporting pinstripes. Both men were unsuccessful as New York had become a city ruled by the Yankees, something the Mets can attest to today.

O’Malley saw promise in Los Angeles and approached Stoneham about the possibility of moving his organization. The Giants owner jumped at the chance, moving the team to San Francisco while the Dodgers headed to Los Angeles.

Both teams left New York following the 1957 season and while it may have been traumatic for the fans of the Big Apple, it turned out to be monumental for the game of baseball. With two teams out west, baseball grew exponentially throughout the latter part of the 20th century.

What began as a simple move of two teams grew into a beloved sport, seen by many across the nation.  

Branch Rickey

When you see the number 42 on the facade of your favorite ballpark you think of Rickey and Jackie Robinson. Any time a minor leaguer receives their call to the majors, they should think of Rickey who invented the modern Minor League system.

Either of these achievements would make Rickey one of the most influential owners in baseball history and he accomplished them both, though one stands out in the hearts of baseball fans.

The integration of Major League Baseball will forever remain Rickey’s legacy and rightfully so. He chose Jackie Robinson from a large group of Negro League players, not just for his exceptional talent, but also for his ability to take the abuse required for the first African-American regular in baseball.

Sure, Robinson had a reputation of fighting back against racism while playing in the Negro Leagues, but his tenacity was appealing to Rickey.

Robinson lived up to his reputation in his first meeting with Rickey, but the Dodgers’ owner convinced Jackie to remember his role as a pioneer in baseball. Robinson agreed not to retaliate against white players who would do everything within their power to prevent this ‘experiment’ from working.

Robinson was also a young player which separated him from more well-known Negro League players like the veteran Satchel Page. Rickey understood the one to break the color barrier had to be the right person, but also young enough to play in the Major Leagues for many seasons. 

Despite the actions of those on the field, Robinson was able to win over the American public with his exciting ability to play baseball. A pure hitter with speed and some power, Robinson was the epitome of a professional baseball player.

Long before breaking the color barrier in baseball, Rickey made his intentions clear in regards to racism in America. He said, "I may not be able to do something about racism in every field, but I can sure do something about it in baseball."

He certainly accomplished that.