Business mogul Donald Trump is scouring waterfronts, depressed mill towns, and vacant rural tracts across Massachusetts, searching for locations suitable for a lavish resort casino that he could develop under Governor Deval Patrick's proposal to legalize casino gambling.
His list of as many as a dozen sites includes undisclosed locations in the Boston area, the region that an industry source said he most desires, as well as the Holyoke Mall and a harness racing track in Plainville.
Executives from Trump's resort development arm, Trump Entertainment, have toured sites in Fall River, New Bedford, and Warren, and they met recently with the mayors of Chicopee and Holyoke, according to local officials, land owners, and an industry source. They also have had extensive discussions with Gary Piontkowski, the owner of the Plainridge Racetrack in Plainville, but no agreement was reached, said the industry source.
Several of the locations are in communities looking for an economic boost that have already expressed a strong interest in hosting a casino, making it more likely local voters would approve a casino if the political and economic stars line up.
"We have a real high elderly population, a poor population, and those are the ones most accepting of casinos," said Holyoke's mayor, Michael Sullivan, whose community has twice approved casinos in nonbinding ballot questions. "I would venture to say that if we gave the voters a choice between biotech and casino gambling, they would pick casino gambling."
Trump Entertainment owns and operates three casinos, all in Atlantic City, but for years has sought to spring from the New Jersey seaboard to open casinos in other states. Its celebrity chief executive, whose net worth is estimated by Forbes Magazine at $2.6 billion, also owns a vast amount of property in New York, Florida, and throughout the world.
Trump has tried for years to make a splash in the Boston market. Most notably, he sought to build a casino, marina, and residential development on Boston Harbor's Long Island in the mid-1990s - a long shot at the time because there was no appetite to legalize casinos in Massachusetts. A meeting was scheduled with Mayor Thomas M. Menino at the Plaza Hotel in New York, but the mayor canceled and Trump's plans never gained political support.
This time around, he joins a growing list of developers who are laying plans to compete for three casino licenses that would be authorized under Patrick's proposal.
The Democratic governor filed legislation last month that would license a resort casino in three separate regions, Western Massachusetts, Southeastern Massachusetts, and the metropolitan Boston area. His proposal faces a stiff fight in the State House, where Speaker Salvatore DiMasi has expressed skepticism and has not set dates for hearings, which will not be held until next year at the earliest.
Trump executives would not discuss any of their intentions, including their search for locations in the Boston metro region. But the industry source said the Boston region would be Trump's top choice because of its large population and tourist base.
"The bottom line is we think that Massachusetts could present an interesting opportunity for our company and our brand," said Tom Hickey, director of corporate communications at Trump Entertainment. "It's an opportunity that we have explored, and that we will continue to explore."
Trump's casinos in Atlantic City have struggled in recent years and in 2004 the company filed Chapter 11 bankruptcy. Earlier this year, Trump reportedly began accepting bids for the properties. Trump Entertainment tried unsuccessfully last year to enter the casino market in Philadelphia, but could not secure one of the two licenses awarded in the city. Similarly, Trump tried to interest Johnston, R.I., in a 500-room hotel and 5,000-slot-machine resort off Interstate 295, but the plans did not gain traction.
Trump's thorough review of the Massachusetts landscape is not unexpected. The gambling industry has expressed strong interest in Patrick's casino proposal.
Suffolk Downs has a proposal already lined up to redevelop its East Boston racetrack. Just to the north, Wonderland Greyhound Park in Revere has been courting partners. The Mohegan tribe of Connecticut has an agreement for land in Palmer, and the Mashpee Wampanoag tribe has plans to build in Middleborough under Patrick's state-license proposals, or under the tribe's own application for a casino under the federal Indian Gaming Act.
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Casino mogul Sheldon Adelson has expressed interest in the Marlborough area, near the juncture of Interstate 495 and the Massachusetts Turnpike.
Under the governor's proposal, the licenses would go out to bid on a rolling basis, allowing developers to compete on multiple licenses. That setup has developers, like Trump, looking at numerous sites across the state to secure several options.
Trump's list of potential sites indicates he could aggressively embrace a multisite approach - seeking to hedge his bets if the legislation is approved and he decides to get in on the bidding. Ultimately, he could sign purchase options on individual properties that he could exercise if he won a casino license.
Eric L. Hausler, senior vice president of development at Trump Entertainment, met with Holyoke's mayor about two months ago to discuss possible scenarios, including buying the Holyoke Mall or the former site of Mountain Park, one of New England's first amusement parks, and building a resort casino on either of those properties.
Building a casino in Holyoke would allow Massachusetts to compete directly with Connecticut casinos. The city is northwest of Springfield at the junction of the Massachusetts Turnpike and Interstate 91, and is located closer to Connecticut's Bradley International Airport than both Foxwoods and Mohegan Sun.
But a Holyoke site also would put front and center the arguments over a casino's impact on social ills. The city of 44,000 is one of the poorest communities in the state, with more than 7 percent of residents unemployed and one-fourth of the population living below the poverty line.
While remaining skeptical over the social costs and uncertain whether casinos will get the necessary legislative approval, Holyoke's Mayor Sullivan says a casino could provide the catalyst the city needs to revitalize its economy.
"It's a challenge for a community like Holyoke, but I'm a pragmatic guy," Sullivan said. "If there's a benefit for the city of Holyoke, I want us to be at the table."
Matt Viser can be reached at maviser@globe.com.