An off-day during the Yankees' push toward a division title in mid-September of 2012 was more like a day at the office for Alex Rodriguez. In his role as president of an apartment management company, Newport Property Ventures, he had papers to sign as an individual guarantor on a loan extension agreement with an original sum of $31.7 million, according to property records in Florida.

To a banker, Rodriguez has been money. Unlike hedge funders in mercurial markets or business owners vulnerable to economic swoons, Rodriguez has always possessed what lenders crave: a guaranteed future fortune. A year ago, despite his calamitous postseason flop, Rodriguez's deal with the Yankees was secure, with $114 million due through 2017, plus a potential $30 million in bonuses for historic home run milestones. Bankers fall over their wingtips for a client such as A-Rod.

Rodriguez's baseball bounty had the endless feel of an infinity pool. But that was before the doping scandal with a name that sounds like a sci-fi flick where everything explodes at the end. Could Biogenesis be A-Rod's margin call? Could it blow up his heavily leveraged world?

In the 11 months since The Miami New Times obtained records that revealed Biogenesis as an anti-aging clinic serving as an alleged hub of PEDs for players such as Rodriguez, he has been spending large sums on public relations firms and celebrity lawyers to fight a 211-game ban by MLB for repeated violations of baseball's anti-doping policy. Why go through an ugly arbitration ordeal, which resumed Monday after a one-month hiatus? Rodriguez was forced to admit to steroid use in a 2009 press conference. The issue is not about the purity of statistics or A-Rod's legacy. This is moneyball. Rodriguez has earned $325 million in his career and would lose $30 million in salary if MLB's ban were to be upheld in arbitration. If Rodriguez testifies during the hearing, and is later found to be untruthful, the ban could reach lifetime status and cost him $86 million, plus bonuses.

Two wealth advisers with knowledge of Rodriguez's portfolio describe him as a savvy investor who has had solid holdings in gold and stock, but who also enjoys risk. He has shown a voracious appetite for investment advice, seeking out Warren Buffett, the Oracle of Omaha, and Dolf de Roos, an author on books for turning real estate into riches. As one adviser explained, Rodriguez is not an athlete "who is content with conservative options and the wealth from his player contracts. He has a big-score mentality." Neither adviser is suggesting Rodriguez is in financial straits, but A-Rod's aspiration has always been to walk among the billionaires he admires. He revels in hedging. He bet on himself when held out as a rookie in Seattle. He bet on his stature when he opted out of his Yankee deal in 2007. He bet he wouldn't get caught when he used steroids as a Ranger.

The money always materialized after the risks. There is a great deal of Donald Trump in Rodriguez. Both live a gilded existence buffed by myth. Both thirst for attention. It is no surprise Rodriguez once lived in a Trump building on Park Avenue in New York City. He fancies himself a high roller, too. In a review of public records and corporate filings, a portrait emerges of a ballplayer with ambitions to be on the Fortune 500 list. Rodriguez does not have endorsement riches to supplement his fortune -- Forbes valued his corporate pitchman ventures at $1 million annually -- but he has other income as the part owner of a Mercedes dealership in League City, Texas.

Also like Trump, the centerpiece of Rodriguez's empire is real estate. Newport Property Ventures, once a thriving operation of complexes around the country with wide profit margins in 2009, is now showing signs of distress. According to Dun & Bradstreet, a financial information service for businesses, the company is at "high risk" of not paying its bills on time and has a "significant" likelihood of facing financial stress within the next 12 months. Messages left for Rodriguez, who is listed as the chief financial officer at the company's Coral Gables, Fla., headquarters, were not returned.

In 2006, Rodriguez founded Newport Property Ventures using $50 million in loans to start amassing apartment complexes, many for low-income families. He was seduced into the real estate froth by de Roos' methodology. In August 2004, Rodriguez wrote the foreword for a book by de Roos, "Real Estate Riches: How to Become Rich Using Your Banker's Money," explaining, "When I landed my well-publicized 10-year, $252 million contract, I set about finding an investment vehicle that would ensure my financial fitness long after baseball." Rodriguez added that de Roos' book gave "me confidence to form Newport Property Ventures. I began by investing in a small duplex in an emerging area of South Florida, which led to the acquisition of several other income-producing properties."

With money to stockpile real estate, the approach was simple back when loans were being handed out like candy at the teller window: Rodriguez ate it up. Like many, he never saw a great recession coming, during which his property values would plummet by more than $18 million and distressed tenants would miss rent payments. Dozens of tenants were evicted from Rodriguez's six Tampa-area complexes in 2009 and 2010, records indicate. In recent years, the company has been the subject of reported complaints from residents who cite rats, mold and structural disrepair across a multitude of complexes. In July, The Washington Post reported that tenants had filed hundreds of complaints with Prince George's County (Md.) officials over dilapidated conditions.

Being a landlord -- or a slumlord, as Rodriguez has been called in some headlines -- isn't a winnable position for anyone, much less a polarizing star who has landed the wealthiest contracts in sports history. Rodriguez has been tone deaf to the criticism, refusing comment and continuing operations that appear to be fraying internally. In a posting in April on Glassdoor -- an employment review website with registered users -- a former maintenance supervisor rated Newport Property Ventures with one star, complaining of a disrespectful workplace, no pay raises for two years and adding, "I'm not optimistic about the outlook of this company."

Rodriguez was a believer last year when he guaranteed a loan extension for his company. At the time, his financial health was certain to sustain his business and personal obligations. In 2008, Alex and Cynthia, his wife of five years, divorced. In the divorce complaint, Cynthia stated the expectation of A-Rod's responsibilities to her and his two school-age daughters:

Child Support: The children need temporary and permanent support from the Husband, and the Husband has the ability to pay. The lifestyle and background of the parties and the children is such that the Husband should provide life insurance, health insurance, private school, and, continue to maintain the existing lifestyle of the children.

Standard of Living: The Husband is a prominent athlete and has, due to his substantial earning power, provided the parties and their children with a lavish lifestyle. The Husband has provided his family with a residence that is compatible with his great wealth and high standard of living. The Husband has the fiscal capacity to continue his high style of living, but the Wife does not.

In court records, Cynthia expected a lump sum payment toward alimony from the couple's home in Coral Gables. It sold for $8.5 million after the couple paid $12 million. The settlement is sealed and there is no public record delineating what other alimony Cynthia received. Alex's child-support obligations vary under Florida law, but state-certified calculators indicate his burden would be at least $200,000 per month. A suspension by baseball wouldn't necessarily mean a modification of that obligation.

"Some judges in particular are very much tuned into creating the lifestyle the children would have if the divorce hadn't occurred," said Mary Ziegler, a professor of family law at Florida State University College of Law, who is not involved in Rodriguez's legal affairs. "Given the amount of money he would have already made -- and given that he has so much disposable income that he has spent outside child obligations -- the court would consider all of that."

A court might ask Rodriguez the following: What else can you do to make money during the ban?

"It's a tricky thing for a court," Ziegler said. "You have to imagine what a person could make if they tried harder. It's a complicated thing to imagine, but based on his skillset and public celebrity, Alex Rodriguez would certainly be vulnerable to that question."

Rodriguez is constantly searching for a profit margin. A year ago, he upset residents of a wealthy enclave along Biscayne Bay when he turned his 21,000-square foot bachelor pad into a film set while he was away. Residents complained when trucks carrying camera equipment for fashion shoots and music videos cluttered the narrow, two-lane North Bay Road. One resident, Irwin Friedman, told the Miami Herald he disagreed with Rodriguez "renting out his property to make money on a commercial enterprise."

The neighborhood can rest easy now. Rodriguez sold the mansion for $30 million this spring, netting a $15 million profit, sales records indicate. Still, neighbors remain incredulous as to why Rodriguez needed to keep pumping the property for money. "He threw some lavish parties there," one resident joked to a reporter on a recent visit. "Maybe he had to pay for that decadence."

Rodriguez has long lived a life of private jets, Maybach cars and five-star extravagances. For most of his career, the public displays of wealth were a way of flaunting his statistical value. He was the highest-paid player in the game, with MVPs as proof of the investment. Four years ago, the perception changed after SI reported his steroid use as revealed by a 2003 test, before penalties were put in place. There were no financial repercussions. Rodriguez played on, earning a World Series ring and adulation after his PED confession. It was as if nothing had ever happened.

Although his body would continue to break down and he would again fail in the crunch of a playoff run -- Rodriguez hit .111 and was benched in an ALCS sweep by the Tigers in 2012 -- his earnings were on a guaranteed roll. Being A-Rod meant never needing a credit check. Being A-Rod meant living on a hedonistic romp even with bad hips -- buy whatever pleasure, whenever it struck -- without pumping the brake. Does Biogenesis turn out the party lights?

Although Rodriguez has poured massive resources into his defense -- suing MLB for conducting a "witch hunt" and the Yankees' team doctor for malpractice -- he also has made moves to preserve funds. He downsized this summer to buy a relatively modest $2 million condo on South Beach. Maybe A-Rod finally is hedging against himself.