In 1995 Donald Trump bought 40 Wall St., down the street from the New York Stock Exchange. The property has proven to be the former president’s most durable connection to public markets.

Trump's complicated relationship with the public markets was in full view this week with the postponement of his potential plans to take his social media venture public. Trump Media & Technology Group had planned to go public via a merger with a SPAC (special purpose acquisition company), but federal regulators are probing the deal and may end up derailing it.

This would not be the first time Trump's dealings with Wall Street went awry. So, why don't Trump and the public markets mix? While Trump may long for the access to capital that comes with a market debut, being traded on the public markets comes with a big condition: regulators have much more power to look into questionable business practices of public companies.

“The public markets do require transparency, they do require filings with the regulators and so there are a lot of checks and balances," Reena Aggarwal, director of Georgetown’s Psaros Center for Financial Markets, noted recently in an interview about Trump.

The announcement in October that blank check company Digital World Acquisition Corp. (DWAC) would merge with Donald Trump's media company sparked immediate excitement from investors. The impending deal also caught the attention of regulators. By December, the Securities and Exchange Commission (SEC) was publicly looking into whether Trump’s company illegally negotiated with DWAC too early.

In a statement Thursday, Trump’s company said the SEC “has needlessly delayed its review of our proposed merger, causing real and unnecessary financial harm to DWAC investors.”

‘It’s the New York Stock Exchange’

This was not the first time Trump courted Wall Street. He led a public company beginning in 1995 when Trump Hotels and Casino Resorts began to trade under the ticker DJT.

“This is such a big day for us, it’s the New York Stock Exchange,” Trump said at the time.