The executive, Abraham Wallach, was used to this sort of thing. It was Wallach and Trump who flew to Hong Kong in 1994 for a crucial dinner with billionaire Vincent Lo to secure financing for a project that Trump, in a published report, called “the biggest [expletive] deal in the history of New York real estate.” And it was Wallach whom Trump sent to Japan in 1994 to gather intelligence and help Trump battle for control of the Empire State Building.

In March 2000, shortly after announcing he would not run for president that year, Donald Trump dispatched one of his top real estate executives to South Korea on an important business errand.


In Seoul, Wallach said, he was going to meet with Daewoo, the Korean conglomerate that was funding construction of the New York skyscraper known as Trump World Tower.

Just days before that flight, though, Wallach went off on an errand of his own, walking out of a Nordstrom store in White Plains, N.Y., with two crystal vases purchased with a credit card bearing the name “Anthony Greto.”

And two months after the scheduled trip to Seoul, Wallach returned to the same Nordstrom with a different stolen credit card. He picked out a $600 Salvatore Ferragamo handbag and — this time with a store security officer watching — signed the name “Meg Osman.”

He was arrested and admitted charging another $1,000 worth of jewelry to the same woman’s American Express card. It was — according to court documents obtained by the Globe — one in a series of similar criminal convictions that would land him, years later, in Rikers Island, the New York City jail complex.

Wallach was one of Trump’s top executives for perhaps the most critical decade of the business magnate’s career. He helped Trump craft multimillion-dollar deals, built relationships with global real estate moguls, and spearheaded projects that would help lift Trump’s businesses out of bankruptcy.


But before, during, and after working for Trump, Wallach was a habitual criminal. Over a period of 30 years, he collected at least 15 arrests in five states, four separate felony convictions — for crimes including forgery, grand larceny, and making false statements to prosecutors — and three jail sentences, according to an extensive Globe review of court records.

Trump was apparently in the dark about all of this until near the end of their long association. Through a campaign spokeswoman, Trump confirmed, however, that he knew of Wallach’s theft habits during the last year he employed him.

In not immediately firing Wallach, “Mr. Trump acted out of compassion,’’ said spokeswoman Hope Hicks. “He recognized this was a sickness and was optimistic Abe would seek the help he needed, which Abe obviously has failed to do.’’

During his presidential campaign, Trump has said repeatedly that he has hired and will hire only the “best people.” It’s a notion that has already been challenged by his choice of campaign staff — among them a former chairman who is under scrutiny for payments tied to pro-Russian interests in Ukraine and a current campaign manager whose wife charged him, in a 1996 case that was later dismissed, with battery. Trump’s employment of Wallach as one of his close business associates raises additional doubt about his hiring practices and acumen.

Wallach, who lives and works in Southampton, N.Y., initially declined to discuss details of his criminal past. “All I’m going to say to you is that whatever happened, happened as a result of dealing with an insane boss who should never be president of the United States,” he told the Globe. “End of point, end of conversation.”


But during a 90-minute conversation shortly thereafter, Wallach provided an elaborate, often agitated account of his time with Trump. He says he told Trump of his theft habit some time “during the last year of my employ,” which he variously lists as 2001 and 2002.

The bizarre tale of Trump and Wallach’s relationship dates back to 1989. At the time, Wallach might have looked the part of the successful real estate man. Then 48, he had two decades of development experience on the New Jersey side of the Hudson, a resume boasting a graduate degree in business from Columbia University, and periodic appearances on television as an expert commentator on the real estate business.

He had also racked up a considerable rap sheet, including a 1982 conviction in New Jersey for possessing stolen art and a 1983 conviction in Florida for grand larceny — felonies that got him a combined five years’ probation. The summer before he met Trump, Wallach was sentenced to three days’ confinement for a theft conviction in Texas.

It was another sort of offense, however, that caught Trump’s attention: In late 1989, Wallach appeared on public television’s “The MacNeil/Lehrer NewsHour” after being invited to comment on the precarious state of Trump’s empire, then teetering near bankruptcy.


“If you pay too much for properties,” Wallach told co-anchor Robert MacNeil, “and if your ego is as large as his is, and you just buy everything in sight, part of the blame has to rest squarely in your own lap.”

Trump sued him for $250 million.

Wallach initially panicked, according to an unpublished memoir about his time with Trump, portions of which he provided to the Globe. Finding a lawyer to serve as a go-between, he agreed to stop talking publicly about Trump, which effectively ended the legal threat. But the lawyer also delivered an unexpected message: Donald Trump wanted to talk to Wallach.

Their introductory phone call began with a harangue (“You shouldn’t knock me,” Wallach remembers Trump bellowing, “because knocking me is knocking New York”) but ended with an invitation to meet and chat about real estate. Wallach came to his office at Trump Tower. After a second meeting there, according to Wallach’s memoir, Wallach agreed to join The Trump Organization as executive vice president for acquisitions and finance — a position he would hold from 1990 until 2001 or 2002.

Wallach says he did not tell Trump of his criminal past at the time of his hiring. Trump confirmed through his spokeswoman that he “was not aware’’ of the prior convictions. “[Trump] knew nothing about Mr. Wallach’s past, and it wasn’t revealed,’’ Hicks said.

But a minimum amount of homework on Trump’s part would have unearthed it easily, according to hiring specialists. “The chances of not finding something like that [prior felony convictions], I would say, are zero,” says Peter Cappelli, a professor of management at the University of Pennsylvania’s Wharton School. “It suggests someone who is more interested in their own gut than in checking and vetting.’’


Trump did not offer comment on his hiring process at The Trump Organization or whether Trump independently checked Wallach’s background before bringing him on board. “This was so many years ago it would require a comprehensive search of records,’’ said Hicks.

She added: “Mr Trump’s judgment is impeccable.’’

The 1982 stolen-art case would have been especially easy to uncover: A reporter for the Newark-based Star-Ledger newspaper covered Wallach’s sentencing.

“There’s no question of my guilt,” the reporter’s article quoted Wallach telling the judge. “I was in possession of those seven paintings.”

Star-Ledger readers, in fact, learned of the case in fairly vivid detail: Wallach had displayed the seven artworks at a dinner party. One of the guests — asked by Wallach to assess their worth — recognized the pieces. They had been stolen from the collection of Morris and Raye Landis. The Landises had been Wallach’s neighbors.

Wallach resigned his position as head of the redevelopment agency New Brunswick Tomorrow and faced a possible 6½ years in prison. But the judge — finding it improbable that “a highly-educated, very accomplished municipal planner” would repeat such behavior — let him off with a fine, psychological treatment, and three years’ probation. By 1989, Wallach had reestablished himself at a pension advisory firm with offices in Houston.

When “The MacNeil/Lehrer NewsHour” sought him out, Wallach first hesitated at the notion of talking about Trump — a man he had a “very low opinion of”— on television. He was turned off by Trump’s love of “glitz,” “limos,” and “gaudy” living, he told the Globe. But his first trip to Trump Tower kindled a different set of feelings. In the words of his memoir: “All of my senses were activated. There was the sound of water splashing from a five-story waterfall.” A great atrium of pink granite. And the experience of being whisked directly upstairs to the man himself: “Suddenly I was in the world of Donald Trump.”

From the outset, Wallach had Trump’s ear and, Wallach says, access to his three giant Rolodexes. He persuaded Trump to tour the crumbling, largely vacant skyscraper at 40 Wall St. and — against conventional wisdom — to buy it. Trump, he told the Globe, gave him a silver keepsake engraved, “To Abraham Wallach, Who Got This Deal Done.’’

Meanwhile, he kept up his sideline as a thief. The things he stole he sometimes presented to Trump Organization colleagues as gifts, he says.

Why did Wallach choose to remain in an environment he describes as “Alice in Wonderland”? “When you’re in a situation long enough,” he says, “you become part of the problem.” By 2000, Wallach had an I [Heart] Donald Trump sticker on his office wall.

Untangling fact from fiction in some of Wallach’s account can be tricky; he says, for example, that he made up of whole cloth one sensational anecdote in his memoir about drugging a competitor to get at the contents of his briefcase.

“I made that up,” he says flatly. “I made it up because a couple people said, ‘You’ve got to [liven the manuscript up], or else people won’t read it.’ ”

Working for Trump undermined his sanity, Wallach told the Globe. Often, he was the man left to sweat the details that Trump would not. While Trump was showing off the lobby of his newly acquired General Motors Building in 2000 — this is verde marble, he told a reporter — it was Wallach who was fretting that the building wasn’t producing enough rent to justify its cost.

Wallach’s starting salary, which he suggested in his memoir was $175,000, was a relative pittance in the glitzy world he now inhabited. When Wallach bought a new home in Pound Ridge, N.Y., he says, Trump gifted him a new bathroom clad in Trump Tower granite. According to Wallach, Trump sometimes invited him to socialize — once taking him, his now-husband, and Trump’s then-wife Marla Maples to a show in Atlantic City via helicopter — though Trump remembers otherwise. “Mr Trump has never socialized with Mr. Wallach,’’ according to his spokeswoman.

It was at about that time, according to the Globe’s review of court records, that Wallach went shopping again in White Plains, in January 2001, signing the name “IJ Miller” for $1,000 of jewelry at Neiman Marcus.

If his self-control was slipping, Wallach’s luck still held: The White Plains judge let him off with probation. When he violated that probation, picking up an arrest near the wealthy hamlet of Chappaqua later that year, his punishment was still more probation. He expanded his activities to Connecticut — just a few miles’ drive from his home in Pound Ridge — and was on probation there, too, for forgery and credit card theft, by October 2001.

At some point — “during the last year of my employ,” Wallach says — he told his boss about his stealing. Trump told him to stop it right away and seek treatment, Hicks said.

In early 2002, according to court records, Wallach’s luck began to run out.

On the first Saturday in April, a man described by police as wearing a long black coat, dark sunglasses, and “quite possibly a toupée” was seen entering the Saks Fifth Avenue store in Greenwich, Conn. The man brought a $1,200 red handbag to the cashier, produced a Saks Fifth Avenue credit card bearing the name “Joyce Robbins,” and left with his purchase.

Two days later, the real Joyce Robbins came to the same cashier and discovered that her credit card was missing from her purse. A Greenwich Police detective was soon asking the store’s loss-prevention officer if he could identify the man. Yes, he said. He’d already had the man arrested, twice, at the Neiman Marcus where he used to work in White Plains. He knew his name.

The detective called Robbins: Did she know an Abraham Wallach? Yes, Robbins said. He was the brother of her best friend.

By the time the detective had pieced the story together — Wallach, it seemed, had gotten the card from Robbins’s unattended purse at his sister’s house during a Passover dinner — Wallach had managed to spend $4,888.33 at Saks Fifth Avenue. And while half that total was rung up in Greenwich, the other half was charged at the Saks on Fifth Avenue in Manhattan — just six blocks down the street from Wallach’s office in Trump Tower.

Convicted of grand larceny — his third felony — Wallach was sentenced to 30 days in a Connecticut prison in January 2003.

In the meantime, Wallach says, he had volunteered to leave Trump’s employ, though he would not provide a specific date of his departure.

“I said, ‘Donald, I’m leaving.’ He said, ‘Why, Abe?’ I said, ‘Because part of the problem is right here.’ He said, ‘Go to Hong Kong.’ ” Wallach could work for Trump from there. “I said, ‘No, Donald. I need to leave.’ ”

Asked for a response to Wallach’s account of that conversation, Hicks, the Trump spokeswoman, called the former executive “delusional.’’

“The company kept him for a brief period of time,’’ she said. “Everyone felt sorry for Mr. Wallach, and we realized he had a problem and needed help.’’

Wallach’s criminal cascade would continue for another two years. After his release in Connecticut, New Canaan police would find him wearing a long black coat while stashing stolen artworks into the trunk of a car (found to contain receipts from 39 fraudulent purchases). New York City police would book him for identity theft after he was caught one block from Trump Tower with an $800 sweater concealed under his coat. Wallach was awaiting sentencing in both Connecticut and White Plains when a court in lower Manhattan convicted him of forgery — his fourth felony conviction — and sent him on a detour to Rikers Island.

Wallach says he and Trump would continue to meet, informally, “two, three times a year,” up until the time of Trump’s announcement for president, and that he even extended a vacation in Buenos Aires to scout potential projects for Trump. Trump’s spokeswoman says merely that Wallach continues to contact him.

Wallach emerged for one more court appearance, in early 2005. In a transcript of the proceedings, a Connecticut judge was clearly at pains to make sense of the man standing before him, calling his crimes so “incongruous” with his career and income bracket.

“Yes,” Wallach said. “I — I recognize that and I sometimes, you know, wonder why.”

“What is Shoplifting Anonymous?” the judge asked. Shopflifters Anonymous, Wallach explained, was a 12-step program to bring his compulsions under control — something he hoped to accomplish “[t]hrough not drinking, through not hanging around with people who think of luxuries and things of that sort as the way life should be lived, but living a clean . . . simple life.”

Court documents from that month listed Wallach’s address as a luxury condominium at 845 United Nations Plaza — commonly known as Trump World Tower.

Matt Viser of the Globe staff contributed to this report.