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THOMAS FARRAGHER

What sort of sentence for Boston’s fallen taxi cab king?

Edward Tutunjian left court in Boston in October. John Tlumacki/Globe Staff/file/Boston Globe

The first time I laid eyes on Boston’s taxi titan I did a double-take.

I knew Edward Tutunjian’s business empire was worth a quarter-billion dollars. I knew about his vineyards in Chile. I had a pretty good idea of the reach of his lucrative real estate holdings in the Fenway and Back Bay.

And yet there he was, wearing a well-worn ball cap in the basement of the city’s biggest taxi garage, standing at the foot of a tall ladder, steadying the thing as a worker above tinkered with a ventilation duct.

What gives with this guy? That’s what I was wondering that day three years ago in the grimy garage around the corner from Fenway Park.

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I can imagine that precise question rattling around in the head of US District Judge Douglas P. Woodlock next week, when Tutunjian stands before him in a third-floor courtroom for sentencing.

Tutunjian ran Boston Cab on Kilmarnock Street, presiding over the city’s largest taxi fleet, and has pleaded guilty to charges that indicate he converted the operation to a criminal enterprise. He admitted to dodging payroll taxes, employing undocumented immigrants, and failing to pay overtime wages.

Prosecutors are asking Woodlock to send Tutunjian to prison for at least two years. He’s already accepted a plea deal that orders him to pay more than $2 million in restitution.

Woodlock will wonder what I wonder: How on earth did this guy — “Mr. Eddie’’ to his large contingent of mostly immigrant drivers — get here?

To hear his friends and family and neighbors tell it, Tutunjian is not your typical crook. He’s a man of decency and honesty. He’d give you the shirt of his back. One of the good guys.

Letters to Woodlock say he’s this kind of guy: Want some Bruins tickets? Take mine. Short on the rent money? Here’s a loan to tide you over. Collecting for a charity? How can I help?

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I worked on the Globe’s 2013 Spotlight Team investigation into Tutunjian’s taxi business and saw another side of him and his business — a seamier side in which cabbies were extorted for petty bribes, routinely forced to pay for gas from the company’s overpriced pumps for tanks they’d already filled, and squeezed to make up phantom shortfalls. Not a pretty picture.

Weeks after the Globe series was published, federal agents — with guns drawn — raided Tutunjian’s garage and began a criminal investigation that culminates Tuesday at the John Joseph Moakley United States Courthouse.

Those two contrary and competing images of Tutunjian — the greedy tax cheat and the benevolent benefactor — are not mutually exclusive. Why? Because life is rarely sketched in black and white. It’s almost always shades of gray.

That’s why it’s not difficult, even considering the crimes to which Tutunjian has pleaded guilty, to empathize with the authors of heart-rending testimonials about the better angels of his nature — testimonials written by his wife and children and those who knew him before the feds closed in.

“Mr. Tutunjian tearfully expressed his deep remorse for his wrongdoing and asked my forgiveness because he had not only hurt his family and friends, but also felt he had become an embarrassment for the Armenian community to which he has been so committed and to the church which is so close to him,’’ the Rev. Antranig Baljian, pastor of St. Stephen’s Armenian Apostolic Church of Greater Boston, wrote to Woodlock

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As Tutunjian faces the judge, the city is left to grapple with what to do with the 362 taxi medallions that he quietly transferred to his wife and kids in July.

Police Commissioner William Evans almost certainly is going to reverse that transfer, deeming Tutunjian’s family unsuitable to carry on the business he began to build in the 1960s when he repaired his own cabs, replaced his own brakes, and changed his own oil.

At one point, he and his wife’s net worth — separate from his businesses — was placed at $10.7 million. Here’s what I can’t understand: Why wasn’t that enough?

Thomas Farragher is a Globe columnist. He can be reached at thomas.farragher@globe.com.