A 28-year-old Wall Street businessman is being investigated over $ 250million losses made by the insurance empire he set up . Alexander Chatfield Burns amassed a huge number of businesses , including several insurance companies , in his mid-20s . Colleagues said he would regular attended cigar clubs , the finest restaurants and even donated wine to the Guggenheim museum in the city . Alexander Chatfield Burns , 28 ( pictured with friend Andrea Johnson ) amassed a huge number of businesses , including several insurance companies , in his mid-20s . But is now facing an investigation after his companies reportedly lost $ 250million . Colleagues said he would regular attended cigar clubs , the finest restaurants and even donated wine to the Guggenheim museum in the city . But the financier is facing growing questions after he booked himself into Bellevue Hospital in New York a year ago and resigned from Southport Lane Management LLC , leaving a series of unusual asset transfers behind , the Wall Street Journal reported . Regulators in Delaware say Southport under Mr. Burns siphoned off millions of dollars of mainstream insurance holdings and swapped them with assets that are either over-valued or worthless . Among them is a painting Mr Burns initially believed to be by Caravaggio , but was later discredited as a copy by three art experts . Since the probe he has moved into a historic building in downtown Charleston , South Carolina . The Journal reported that Mr Burns had two insurance companies , two offshore reinsurers , a brokerage firm and a web of dealings with other insurers . His massive portfolio left him in charge of investing hundreds of millions of dollars in additional assets . Regulators seized control of the two main insurance companies last April . One based in Delaware is being liquidated , one in Louisiana has been sold . The insurance-company losses total nearly $ 250 million . Regulators in Delaware say Southport Lane Management under Mr Burns siphoned off millions of dollars of mainstream insurance holdings and swapped them with assets that are either over-valued or worthless . According to court documents obtained by the Journal , the companies still active have tens of millions of dollars in questionable assets . James Denlon , a Louisiana Insurance Commissioner , told the newspaper Mr Burns 'apparently is convincing and good at snookering regulators . ' Jeffrey Leach , a former president at Southport , told the Journal he wanted to be a 'superrich guy ' . 'His goal was to build this into a multibillion-dollar insurance operation , ' he added . In statements sent through his lawyer , Mr Burns has called a lawsuit started against him by former employees Southport is 'baseless ' . He blamed 'highly unexpected ' events at the insurance companies which prompted a restructuring . He added that Southport complied with all relevant laws and that he does n't face any litigation . Mr Burns has not been accused of any wrongdoing and is not party of any criminal or civil proceeding .
Alexander Chatfield Burns built a portfolio of businesses in 28 . Enjoyed private cigar clubs and would attend the best restaurants . Financier facing growing questions following a stay at Bellevue Hospital . He later resigned from a company he founded , Southport Lane . Regulators say he siphoned off millions of insurance holdings and swapped them with worthless assets .