Michael Stoler — Casinos, gaming and horses, oh my!

Becoming successful in real estate is not easy. Not only does it take a stomach for risk, it also takes the ability to bounce back from failed projects — as many are trying to do now.

But once real estate executives achieve a certain level of success, they often seem to branch out to other areas of business.

For a while, the preferred next area seemed to be banking. Then, it was professional baseball and football teams. Now, all bets are off — or should we say on? — as a rush of real estate moguls get into horse racing and gaming, with the properties associated with these activities available at discounts.

The list of real estate bigwigs who went the banking route have included Howard Milstein (Emigrant Savings Bank), the late Stanley Stahl (Apple Bank for Savings), Moshe Marx (Berkshire Bank), Stephen Rosenberg (Greystone Bank), Shaya Boymelgreen (LibertyPointe Bank) and David Lichtenstein (Park Avenue Bank). The latter two banks were taken over by the FDIC last year. Meanwhile, in 2009, Stephen Ross, chairman of the Related Companies, and two other top executives at the firm — Jeffrey Blau and Bruce Beal –created a financial firm, SJB National Bank, to buy failed banks. That same year, the LeFrak family invested in Florida-based Bank United and then in Metro Bank in London the following year.

Over the last decade, a number of successful real estate leaders have also been investing in their hobbies — which include big moneymakers like baseball and football. Fred Wilpon, head of real estate investment firm Sterling Equities Associates (and more recently, a Madoff victim), is the principal owner of the New York Mets. In February 2008, Related’s Ross famously purchased 50 percent of the Miami Dolphins football team, its venue Dolphin Stadium and the surrounding land from Wayne Huizenga for $550 million. A year later, he completed his purchase of 95 percent of the franchise for $1 billion.

Meanwhile, Bruce Ratner is the minority owner of the New Jersey Nets, after heading up an ownership group that paid $300 million in 2004. (The Ratner coalition beat out a similar offer by another real estate mogul, Charles Kushner, and former New Jersey Governor Jon Corzine.) And, the Wilf family of Garden Homes — headquartered in New Jersey and one of the largest homebuilders in the nation — bought the Minnesota Vikings for $600 million in 2005.

Lately, though, it seems that the investment area of choice is horse racing and gaming.

With consumers cutting back on spending during the recession, “destination” resort sites like Las Vegas and Atlantic City “got hammered in the past couple of years,” explained New York Gaming Association President James Featherstonhaugh. That opened up opportunities for investors to scoop up real estate in those locations on the cheap.

Last year, for example, Starwood Capital, headed by longtime hotel industry executive Barry Sternlicht, acquired a substantial piece of bankrupt Las Vegas casino operator Riviera Holdings Corp. through a reorganization plan.

“Most people think [Starwood] did that because they wanted an entry into that market at a reasonable price,” Featherstonhaugh said.

In New York, developer Morris Bailey (who heads up both JEMB Realty Corp. in the United States and Busac Real Estate in Canada) teamed up with Dennis Gomes, a former Atlantic City gaming executive, to get a piece of the action. The two spent only a bargain-basement price of $35 million to acquire the Resorts Casino in Atlantic City, a huge drop from the $140 million paid by Colony Capital for the property the last time it sold, in 2001.

In June of this year, Bailey, a long-time owner of thoroughbred horses, also took over Monmouth Park in Long Branch, N.J., as well as the off-track wagering facility in Woodbridge, N.J.

He also has licenses to build four additional off-track wagering facilities.

Meanwhile, Jeffrey Gural — chairman of Newmark Knight Frank and a principal owner of Newmark Holdings (which owns and manages office and loft buildings in New York) — has spent close to six months negotiating to take over the operations of the Meadowlands Racetrack in East Rutherford, N.J. Currently the owner of Tioga Downs and Vernon Downs racetracks in upstate New York, both of which have slot machines that supplement horse racing profits, Gural is expected to step in at the Meadowlands in September.

Gural’s partners are also involved in gaming.

Newmark CEO Barry Gosin and company president James Kuhn purchased the Bethlehem Steel site in Bethlehem, Pa., in 2004 through their entity KG Urban Enterprises. They negotiated a joint venture with Las Vegas Sands for a gaming license, converted the facility, and in 2009 the Sands Bethworks Casino opened for business.

While it may look easy to become successful in a new field, it takes hard work, tenacity and chutzpah to grow in these other businesses and to thrive in real estate simultaneously. In other words, they’re not just playing a hunch.

Additional reporting by Candace Taylor