The upper echelon of horse racing purses has come a long way in 100 years, but the entrepreneurial spirit and promotional creativity of those tasked with putting on the sport’s biggest races burns as brightly now as it did when the racetrack boom of the late 19^th and early 20^th Centuries brought many of today’s most popular venues into existence.

From the days of Santa Anita Park’s infancy in the 1930s and its annual “Hundred-Grander” – the Santa Anita Handicap – to the shot heard ’round the racing world from the Chicago suburbs in 1981 with the inaugural Arlington Million, there’s been no shortage of grandiose plans to up the ante from racing magnates as they strive to attract the best horses in training to their facilities.

Now, Frank Stronach has taken a giant leap forward into uncharted territory by devising a unique financing structure for the new world’s richest race, the $12 million Pegasus World Cup Invitational at Gulfstream Park on Jan. 28.

Time will tell if the Pegasus will be a lasting success and anchor a new, permanent position on the racing calendar to accompany the Dubai World Cup Carnival, the Triple Crown races, the Breeders’ Cup World Championships, and other global prestigious and lucrative events – although having California Chrome and Arrogate scheduled to compete in the first edition provides an added boost of major proportions.

For now, with the aid of the lamentably discontinued Thoroughbred Times Almanac, let’s take a look back at important milestones in racing history that brought the sport of kings to its new Pegasus moment.

1926 – Horse racing had struggled to maintain a foothold in American sporting culture during the first quarter of the 20^th Century due to anti-gambling laws, a precipitous decline in bloodstock and the nation’s plunge into World War I. But the “Roaring Twenties” witnessed a rebirth, with pari-mutuel wagering taking hold and new venues opening across the continent. In 1926, Washington Park in Chicago reopened and brought back the American Derby, a leading race of the late 19^th Century that had been run only once from 1905 to 1925. The 1926 renewal, won by Boot to Boot, offered a $100,000 purse – the first in U.S. racing.

1930s – The first race routinely associated with six figures, the Santa Anita Handicap, stood in contrast to the widespread socioeconomic despair of the Great Depression. Charles Strub and Hal Roach opened Santa Anita at its current picturesque location at the foot of the San Gabriel Mountains in 1934, and promptly devised a signature race with a $100,000 purse to spin the turnstiles. Known for decades as the “Hundred-Grander,” it now informally goes by the “Big ’Cap,” and its list of winners reads like a roll call for the Hall of Fame. Azucar, with George “The Iceman” Woolf aboard, took down the first running in 1935. The legendary Seabiscuit would follow in 1940, his final race, defeating 1939 winner and stablemate Kayak II and becoming at that time the sport’s all-time leading money winner.

1962 – The Kentucky Derby offered its first $100,000 purse in 1946, Assault’s Triple Crown season, but in general, races in New York, California, and Illinois set the money standard during the postwar boom years. The Santa Anita Maturity (now called the Strub Stakes) broke the $200,000 barrier in 1951, and the inaugural 1953 Garden State Stakes in New Jersey, won by Turn-To, reigned as the world’s richest race for most of the 1950s, surpassing a $300,000 purse in 1956. In 1962, the Arlington-Washington Futurity, a premier stakes for juveniles run at Arlington Park, was the first to break the $350,000 barrier, and it would hold the title as the richest race in North America until the Hollywood Gold Cup in California offered a $500,000 purse in 1979.

1981 – Arlington figured prominently as a benchmark venue for lucrative purses throughout the 20^th Century, so it comes as no surprise that the racetrack northwest of Chicago would make history by holding the first million-dollar race. The inaugural Arlington Million Stakes running endures in racing lore for far more than the purse, though, as it was a high point of future Hall of Famer John Henry’s first of two Horse of the Year campaigns. The modestly bred 6-year-old gelding charged from behind under Bill Shoemaker to take the first Million in an absolute thriller over The Bart, and he would win it again in 1984 on the way to his second Horse of the Year award. The Million’s status as the world’s richest race would not last for long, but the event endures as the centerpiece of Arlington Park’s International Racing Festival to this day.

1984 – John Gaines can be credited with several important innovations in the world of Thoroughbred racing and breeding, but perhaps none will ultimately prove to be as influential and long-lasting as his vision of a World Championships for international racing funded by stallion and foal nomination fees. Announced by the Gainesway Farm owner during Kentucky Derby week in 1982, 2 ½ years later the first Breeders’ Cup was held at now-vanished Hollywood Park, the one-day event broadcast in its entirety on NBC. The main event, the Breeders’ Cup Classic, was won by Wild Again and became the new world’s richest race, with a $3 million purse. It would hold that distinction for 10 years.

1996 – International races intermittently surfaced as the world’s most lucrative during the late 20^th Century – the English Derby in 1980, the Japan Cup in 1994 and 1995 – but it took another far-ranging and grandiose plan from a titan of the Thoroughbred world to raise the monetary bar well into the 21^st Century. Sheikh Mohammed bin Rashid al Maktoum, the ruler of Dubai and the founder of the Godolphin/Darley racing and breeding conglomerate, unveiled the Dubai World Cup Carnival in spring 1996, a racecard culminating with the $4 million World Cup.

The inaugural festivities kicked off in transcontinental style as Allen Paulson’s 1995 Horse of the Year Cigar shipped to Nad al Sheba Racecourse and captured the 1 ¼-mile World Cup as the 14^th of his 16 consecutive victories en route to a second Horse of the Year Eclipse Award. The Breeders’ Cup would respond by nudging its purse for the Classic to the $4 million mark in 1996 (won by Alphabet Soup), but the Dubai World Cup purse jumped to $5 million in 1999 and then to $6 million in 2000, where it remained for the next 10 years.

2010 – The Dubai World Cup Carnival moved to Sheikh Mohammed’s state-of-the-art Meydan Racecourse in 2010, and the purse for the World Cup skyrocketed to $10 million for the inaugural running. Meydan’s main track featured a synthetic Tapeta Footings surface and, not coincidentally, U.S.-based horses saw their previously competitive performances in the world’s richest race slip over the next four years, with only 2011 Kentucky Derby winner Animal Kingdom (who also won on turf and synthetic in the U.S.) capturing the World Cup in 2013. Meydan installed a dirt surface on its main track for 2015, and California Chrome carried the U.S. back to prominence by finishing second in the World Cup that year before winning it impressively in 2016.

2016 – Next week’s Pegasus World Cup is a step into the unknown, and it will be interesting to see if the 12-horse field, $1 million entry fee for a starting-gate spot and revenue-sharing model will be sustainable. The Grade 1 stakes it replaced on Gulfstream Park’s racing calendar, the Donn Handicap, offered a purse of $500,000 in 2016.

In addition to setting a new acme for purse distribution, the Pegasus World Cup Invitational could signal a significant change in the all-time earnings leaderboard for Thoroughbreds.

California Chrome, who to date has earned a shade over $14.5 million as the leading earner in North American racing history, could vault to the international top if he wins the Pegasus and receives the $7 million winner’s share. The current international leader, taking into account currency conversion rates, is Japanese Triple Crown winner Orfevre, who bankrolled slightly more than $19 million in career earnings.