With Donald Trump continuing to dominate the presidential race, Bobby Cuza takes a closer look at his business record in his three-part series, "Trump and the City." In part one, he looks back at some of the Manhattan real estate deals that first made Trump a household name. 

Before he was a reality TV star and bombastic candidate, Donald Trump was a builder with audacious plans, like buying the dilapidated Commodore Hotel on 42nd Street and turning it into the Grand Hyatt, a success story that became a linchpin for the area’s revival. It helped that he secured a controversial 40-year tax abatement.

Sid Davidoff has been around New York politics since he worked for Mayor John Lindsay. He notes Trump bet big on Manhattan when no one else would.

“He understands how to use the system," says Davidoff.

The son of developer Fred Trump, who built middle-class housing like Trump Village in Coney Island and was longtime friends with Mayor Abe Beame, Donald used political connections to his advantage.

"The city was going bankrupt, you couldn't buy it's bonds. Who was going to invest in the City of New York? This guy stepped up and said I'm going to do it," Davidoff says.

Trump also used his connections to acquire two of Manhattan’s largest undeveloped tracts of land on Manhattan's West Side, the old Penn Central railyards. On one, he convinced the state to build the Javits Center, though he failed in a bid to have it named after his father.

The other, where Trump once sought to build a 150-story skyscraper, would eventually become Trump Place – also known as Riverside South.

“Donald, you performed a great public service,” said then-Mayor Ed Koch in 1986.

Then there was Wollman Rink, which Trump volunteered to reconstruct; he did it in just a few months, under budget—where the city had failed for six years.

Then-parks commissioner Henry Stern said it was a win-win.

"Trump would boast that only he could do it, and Koch said, 'Okay, then do it.' And he cleared the way," said Stern.

Initially, Trump even agreed to donate any profits from the rink to the parks department and private charities. Today, under contracts with the city, the Trump Organization operates not only Wollman Rink, but also the nearby carousel and the Lasker Rink on the northern end of the park.