NEW YORK (CBSNewYork) – Maybe the fourth time is the charm.

Michael Bloomberg is revving up to run for president in 2020, making him both the oldest and richest person to seek the job.

Bloomberg considered running in 2016 as an Independent, but sources tell CBS2’s Political Reporter Marcia Kramer that if he runs in 2020, he would run as a Democrat.

A source close to the former three-term mayor says the move is fueled in part by regret that he didn’t stay in the race in 2016, because he feels he could have either won outright or prevented Donald Trump from winning.

Recent appearances by Bloomberg show a growing frustration with the direction the country is going in, but it’s anyone’s guess whether that will translate into a full-fledged presidential campaign. The 76-year-old would be the oldest person to run for president, but longevity runs in the family. His mother, Charlotte, lived to be 102.

Political consultants point out Bloomberg is making a number of key moves, including spending $80 million to help Democrats win Congressional races and collecting a lot of political IOUs in the process. But, they also say it could be an uphill battle because of his liberal policies.

Baruch College Professor Doug Muzzio says Bloomberg is wise for getting involved in the congressional races.

“That’s a political chits,” he said. “That’s a lot of winners or loyal losers so one can look at it cynically and say he’s building a political organization, a political base.”

Bloomberg considered a run for the White House in 2008, 2012 and 2016. This go-round, he joins a long lost of presidential wannabes right here in the Tri-State Area. Governor Andrew Cuomo, Mayor Bill de Blasio, and Senators Kirsten Gillibrand (D-NY) and Cory Booker (D-NY) have all voiced a desire to run.

With a $51 billion fortune, Bloomberg surely won’t have to hold fundraisers. In 2016 he said he was ready to spend $1 billion on a potential campaign.