The Horse Racing and Gambling Capital of the Midwest

By John Hmurovic
July 2019

There was a time when we were the horse racing and gambling capitol of the Midwest. There were three horse racing tracks in the far northern end of Hammond, a boxing arena which hosted championship bouts, and an off-track betting facility that drew thousands. The full story could fill a book. So, let’s just look at how it all came about, and what it looked like at the start of our brief reign as a gambler’s paradise.

The starting date for this story is July 31, 1892. On that day, Hammond Mayor Thomas Hammond, and City Attorney Robert Gregory stood on an isolated field on the state line. Across the line was 107th Street in Chicago. As the two men stood there, they could look north to a beautiful view of Lake Michigan, or to the east and see the shore of Wolf Lake. But most of their attention was probably focused in two other directions. They certainly looked west, to the train tracks across Indiana Boulevard. That’s the direction from which their guests would come. And, they probably looked south, across the empty, sandy field that stretched to 112th Street. It was that piece of real estate that was of interest to their visitors from Chicago

“Blind John” Condon, as he was known to friends and foes, was a native of Logansport, Indiana who was a major part of organized gambling in Chicago in the late 1800s and into the early 1900s. By establishing the first horse racing track in the Roby section of Hammond in 1892, he was also the first person to bring organized gambling to Northwest Indiana. He was called, “Blind John,” because in the politically incorrect era of the late 1800s, that’s how some referred to those, like Condon, who were losing their eyesight.

Heading the group of twelve from Chicago was John Condon. In an era before political correctness, he was commonly referred to as “Blind John.” A native of Logansport, Indiana, the 38-year-old Condon was in the early stages of losing his eyesight. But, in 1892, he was a king in the Chicagoland gambling world.

Condon made most of his money through bets on horse races. He didn’t make the bets. He controlled the bets made by others. He was one of the primary owners of Chicago’s Garfield Park racetrack. Throughout 1892, reformers wanted Garfield Park shut down, and applied pressure to wipe out gambling in the city. “The people of Chicago, with the exception of the criminal classes, want such places as Garfield Park track closed up,” said the Chicago Tribune.

Condon and associates needed a backup plan, just in case the reformers succeeded. That’s why they traveled to Indiana on July 31, 1892. If betting on the horses was going to be banned in Chicago, they were ready to do the next best thing: They would operate a track in Indiana, just a few inches outside the city limits.

In September, Garfield Park was shut down after two policeman and a horse owner were killed after they exchanged gunfire at the track. Condon and his Garfield Park colleagues were ready. They had reached an agreement with the property owner and the mayor of Hammond. Work began within days on what was called the Roby racetrack.    

The view of the site where the Roby race track once stood, looking at it from its southern end on 112th Street. The houses on the left side are on State Line Road in Chicago, but everything else in the photo is in Indiana. The horse track’s stables stood on the southern end, near 112th Street, in the foreground of this photo, while the track would have been in the background, where the power lines now stand.

Today, you can see where the track was as you travel on Indianapolis Boulevard to or from Chicago. Look south at the state line. The land south of the “Welcome to Indiana” sign and the eastbound entrance to the Indiana Toll Road is where the Roby racetrack stood. The track stretched from 107th Street on the north, to 112th Street on the south. Its western boundary was, literally, the line that separates Indiana from Illinois. On the east, the track property extended a half-mile from the state line. Today, that land on which the track stood is once again an empty field, except for the giant electric power line towers that stand on it, and except for a portion of the Indiana Toll Road which sits on what was the eastern part of the track.

“What if Chief McClaughry (Chicago Police Superintendent at the time) and his police shut down the Garfield Park track,” one of the owners of the Roby track said. He bragged that the new Indiana track would be so close to Chicago, “that if a fence were down, all you would have to do would be to step across the imaginary boundary line out of Chicago and into the big racetrack grounds.”

The new track was going to be a gold mine for the owners. That’s what the Inter-Ocean, a Chicago newspaper of the time said, especially if Chicago was intent on making gambling more difficult in the city in the wake of the Garfield Park shootings.  Roby, the paper said, could prove to be a brilliant “scheme of horse racing among the Hoosiers, for the patronage of Chicagoans.”

To this day, the Roby section of Hammond is still an area in Indiana designed for the patronage of Chicagoans. When Illinois laws limited gambling, a casino was built in Indiana to lure Chicago gamblers this way. When city regulations limited big box retail stores in Chicago, Wal-Mart built one of its stores across the line in the Roby area. Laws prohibiting the sale of fireworks in Illinois is why so many fireworks sales are just across the line in Roby, just as Illinois taxes on cigarettes and gas explains why there are so many gas stations and cigarette shops in Roby.

This map, from an 1892 edition of the Chicago Inter-Ocean newspaper isn’t precisely drawn. Wolf Lake, for instance, is in both Illinois and Indiana. But it gives a rough idea of not only where the race track was located, but also for some of the plans the developers of the track initially talked about, such as the hotel and club house. Hyde Lake no longer exists, filled in many years ago, but the woods south of the track remain as the Cook County Forest Preserve. The land where the track stood was very sandy, with numerous small oak trees on it.

The name Roby is fading from common use in Whiting-Robertsdale. It used to have residential areas and its own post office. Its unofficial boundaries were Lake Michigan on the north, the waters of Wolf Lake to the south, and the state line on the west. There’s some debate on its eastern boundary, but it extended at least as far as the channel of Wolf Lake, and at most just a short distance east to the Five Points intersection of Calumet Avenue and Indianapolis Boulevard. The area was named after Edward H. Roby, who bought 600 acres of land there in 1873.   

“Magnificent,” was one of the words Condon and associates used when they looked at the site in 1892. “Nature intended this for a racetrack,” said the man who designed the track at Garfield Park and Washington Park in Chicago, and who was now tasked with the job of designing the Roby track.     

A photo in a 1901 edition of the Chicago Tribune shows us what the paddock at the Roby race track looked like. The paddock was an area to hold and exercise horses. The track had stables to accommodate as many as 500 horses at a time.

The land was sandy, with lots of small oak trees on it. There was a grove of oaks, “so thick that a horse could scarcely walk through it,” at the end of one stretch of the track. The track was sandy, but that was touted by the owners as a positive. They intended to have winter races. The sandy soil would not get sticky, the way that regular dirt tracks might on a wet day, and the sand would become more solid as cold temperatures moved in. It was a mile-long track, 75-feet-wide. The stretches and turns were each a quarter mile long, with the backstretch running along the state line.    

At the south end of the site, along 112th Street, were two rows of stables. Each was about 1,000 feet long. Between the two rows was a space of 24 feet. That 24-foot-wide, 1,000-foot-long space was enclosed with a roof, giving the trainers and jockeys a place to walk their horses that was protected from the rain and cold. There was an opening every seventy-two feet in the 1,000-foot-long structure, each opening with a sliding door, to allow access into and out of the stables. Another set of stables, this one 1,500-feet-long, was built on the east side of the track. In all, there were stables to accommodate 500 horses.

Initially, the horse racing track was called the Roby track. But after two other tracks were opened nearby, the Roby track became known as the Lakeside track. Horse racing in Roby was during the winter months, so the grandstand was enclosed. Spectators could watch the races through the glass windows. Still, judging from the 1901 headline, the Chicago Tribune was not a fan of the grandstand.

A grandstand was built facing west. It was just over 300 feet long with space for 5,000 spectators. It was enclosed, with the side facing the track made of multiple panes of glass. The roof was self-supporting, which meant it was free of pillars that might obstruct the views. It was painted Nile green. Since most of the racing was to be done in the winter months the grandstand was heated with natural gas.

Twelve furnaces provided the heat. All were positioned under the grandstand, which was one large room with a low ceiling. The furnaces shared the space with a restaurant and a bar. Electric arc lights supplied the lighting. But the heart of the area below the grandstand was the betting ring.

A pool room, in the late 1800s, was a place where bookies would pool the money of gamblers for the purpose of making bets. This is what the pool room looked like in Roby, drawn by an artist for the Chicago Inter-Ocean newspaper in 1899. Near the top of the drawing are the words “New Orleans” and “Ingleside.” Those are names of tracks where races were being held on that day. Below those names are blackboards, staffed by men writing the names of the horses and jockeys in those races, the odds for each horse, weather conditions at the track, and other information gamblers needed to make their bets. In the language of the time, betting on races held outside your own track was called betting on “foreign” races. Today it is called “off-track” betting. Notice the furnace on the right side of the image, providing heat for the gamblers, since the races at Roby were held in the winter months.

For those who arrived at Roby before the races began, a blackboard listed races on other tracks: Guttenberg in New Jersey, just outside of New York City; Gloucester, also in New Jersey, but close to Philadelphia; and Nashville, among others. Weather conditions at each of those tracks were also written on the blackboard, as were the odds for each horse to win. The names of the jockeys were written in green chalk. Gamblers could place their bets on these “foreign” races, as they were called.

“They’re off at Guttenberg, boys,” an announcer seated at the betting platform yelled out when the race began at the New Jersey track. He was getting his information from a telegraph wire. “At the quarter-mile; Dewdrop is in the lead.” Twenty races were run on these foreign tracks on a day when an Indianapolis News reporter visited and wrote about it. “Thousands of bets placed, and thousands of dollars lost on the names on the blackboards,” he added.

The horse races in Roby drew regular people, as well as celebrities of the era, both in the grandstand and on the track. James McLaughlin was one of the greatest jockeys of the 1880s, and a future hall-of-fame inductee. His most famous race may have been onboard Hindoo, a hall-of-fame horse, in the 1881 Kentucky Derby. McLaughlin was retired from riding by time the Roby track opened in 1892, but he served in the key role as the race starter in the first season at Roby.

The track did not directly manage the betting. Instead, bookies paid the track for the right to take bets. The number of bookies working varied from day to day, but on opening day, November 12, 1892, fifteen bookies were at work at the Roby track. As race time neared, the bookies would wait for a signal from the judge’s stand to allow them to start taking bets on the upcoming race. Each bookie had his own blackboard and posted his own odds. A bell signaled the start of the race. Some of the bettors walked out to the track to watch, but according to the Indianapolis News reporter, two-thirds stayed inside the betting ring, not interested in seeing a horse race as much as being interested in winning a bet.  

The newspaper reporter visited the grandstand. The crowd was sparse. He said there were more people in the betting ring than in the grandstand seats. Most of those in the grandstand were women. Even though the betting ring under the grandstand was not considered a proper place for a lady of 1892, the women were given a chance to place bets. A young man in a uniform, and wearing a cap bearing the words, “Official Pool Buyer,” walked up and down the aisles with a notepad and pencil to take bets.

The track was not an immediate success. There were plenty of critics. “The entire track was done in 61 working days,” wrote a columnist in the Chicago Daily News after attending on opening day. “It looked so,” he added. “The grandstand was a temporary affair, built very much like a store in Kansas, with an idea more to comfort than beauty.”

Other complaints said the grandstand was too close to the track. Some said the sandy track was slow. “A worse track has seldom been raced over,” a critic wrote in the Chicago Tribune. Others complained that the betting ring was too narrow to handle the crowd of gamblers. And there were numerous complaints about winter racing. The track owners wanted it in order to make money year-round, but others complained that it was cruel to horses, and that it only attracted the owners and horses who could not compete against the best horses. Despite days when the track was covered with snow and cold temperatures moved in, horses ran through December and January.

The railroads ran special trains to the Roby track, the fare was usually 25 cents, round-trip. Ads, such as this one from 1896, ran regularly in the Chicago newspapers. The trains were often full, with 1,500 people on-board from Chicago to Roby. On a handful of occasions, they didn’t bother to stop along the way, because there was no more room for passengers. A platform was built along the rail tracks at Roby, which were just north of the race course, and a raised wooden sidewalk led from that platform to the gate of the race track.

The biggest complaint against the track in its early days was with rail service to and from Roby. There was a platform built along the track north of the track to accommodate racegoers, and there was a raised wooden sidewalk leading from the platform to the track entrance. The problem was with the train schedules. After the last race, people would often have to wait an hour before a train arrived to pick them up. It took several days for the problem to be worked out, but once it was, the track became moderately successful.

Newspapers of the time speculated about whether it was making money, but the owners talked of future plans, such as building a hotel, a resort along the Lake Michigan shoreline, and they looked forward to the Columbian Exposition in Chicago in 1893, and the hope of luring World’s Fair visitors to Roby to bet on the horses. There was talk of starting regular steam ship rides across Lake Michigan from the World’s Fair grounds to Roby.

In many parts of early America, black slaves were often the ones to care for horses. In the post-slave era, the children and grandchildren of those slaves learned the skills developed by their ancestors. As a result, by the late 1800s, some of the best horse trainers and jockeys in America were African-Americans. Jimmy Winkfield was one of those. He raced at the Roby track early in his career. By 1900 he was already considered one of the best, and he won the Kentucky Derby in 1901 and 1902. But racial prejudice against blacks grew in the early 1900s, and Winkfield and other black jockeys and trainers were often unable to find work on American race tracks. Winkfield had to go to Russia to do the work he loved, and in which he excelled. There, he was treated as a celebrity. He stayed in Russia until the Russian Revolution of 1917, then moved to France where he continued to work until the outbreak of World War Two. With over 2,600 career wins, he is a member of the horse racing hall-of-fame.

Other problems began to develop. There were questions about the legitimacy of races, especially after a jockey was caught using an electric current in his spurs to urge his horse to move even faster. There were questions about safety for spectators, with regular reports of fights and beatings among some of the rowdier racegoers.

But it was legal issues which ultimately killed the track. Opposition to any kind of gambling was strong in Chicago, and in the rest of Indiana. The issue came to the forefront when the Chicago gambling community branched out into prize fighting in 1893. They constructed a 12,000-capacity arena near the Roby track, and booked numerous fights. Prize fighting was illegal in Illinois and in Indiana, but Indiana law did allow exhibitions of the “manly art of self-defense.”

At the time, Hammond had not grown far north of its center along the Grand Calumet River, so there was virtually nothing between Roby and Hammond. The owners of the Roby track and boxing arena believed that the wilderness between Hammond and Roby would discourage any interference from local police.

What they didn’t count on was the pressure put on state government to stamp out any form of gambling in the state of Indiana. “Indiana will have the unenviable distinction of harboring the foul nest, and the moral responsibility of for all the crimes committed there,” wrote the Indianapolis News. “We shall be fostering the most loathsome lewdness and a series of practices graduating from brazen-faced cheating or open robbery to the commission of murder.”

North is to the right in this map of the far Northwest corner of Indiana, which means Lake Michigan is to the right. The Roby race track was built in 1892, and can be seen on this map at the line which shows the east limits of Chicago. In an attempt to shut down the Roby track, the Indiana Legislature passed a law limiting tracks to a 15-day period of racing, to be followed by 60 with no racing permitted on that track. The race track owners skirted that law by simply building two more tracks in the same area. One would run for 15 days and shut down, as required by law. Then one of the others would open, run for 15 days, and shut down. Then the third track would run, until the 60 days were up on the first track. The other two tracks were called Forsythe and Sheffield. Based on this map, Forsythe was in the vicinity of today’s Unilever plant at the intersection of Indianapolis Boulevard and Calumet Avenue. Sheffield, based on this map, was located just north of 119th Street, south of Indianapolis Boulevard, east of Calumet, and west of today’s Lake Avenue. Houses on today’s Davis and Stanton Avenues now stand where the Sheffield track was located.

Crowds of 6,000 were common at the prize fights, and it wasn’t unusual to have a daily attendance of 1,500 at the gambling boards, betting on races at other tracks even when the Roby track was closed for season. It was too much for Indiana Governor Claude Matthews to ignore. He sent in two companies of the Indiana State Militia in 1893 to shut it down.

The battle between Indianapolis and Roby raged on for years. When the militia left, the gambling resumed. When the Indiana legislature passed a law allowing only 15 days of racing in a meet, to be followed by a 60-day period with no racing, the track owners built two more tracks to get around the law. They would have 15 days of racing at the Roby track, followed by 15 days at their Forsythe track, located on the site of the current Unilever plant, followed by 15 days at their Sheffield track, located in what is today a residential section just south of the Five Points intersection and north of 119th Street.

The back and forth battle waged on until 1905, when the passage of new laws in Indiana, and a period of more openness to gambling in Illinois made the Indiana tracks not worth the effort any longer. The Roby track eventually became a track for auto racing. That gave way to the construction of the Indiana Toll Road in 1955, with much of the land that had been the track taken over by the new highway.