New York Times (May 18, 2015) - In most professions, it would take only one or two acts of egregious conduct before troubled employees were shown the door. In the case of one stockbroker who has repeatedly had complaints from investors, it took 69 customer disputes filed over the last 13 years before he was barred from the business.

The stockbroker, Jerry A. Cicolani Jr., had complaint after complaint documented in his formal record. Regulators and employers spotted red flags. Yet the organization primarily responsible for monitoring the nation’s 637,000 brokers, the Financial Industry Regulatory Authority, did not bar Mr. Cicolani until September 2014.

The Securities and Exchange Commission had already sued him, in May 2014, over his role in a Ponzi scheme. His most recent employer, PrimeSolutions Securities, based in Cleveland, fired him a day after that lawsuit was filed. And his customers had lodged complaints as far back as 2002.

Last month, the F.B.I. charged Mr. Cicolani with selling unregistered securities to 39 investors who lost $7 million. (Mr. Cicolani pocketed $5 million in commissions, authorities say). On May 1, he pleaded guilty to two criminal counts, including one count of selling unregistered securities, in United States District Court for the Northern District of Ohio. He will be sentenced on July 24.

Mr. Cicolani’s lawyer in Cleveland, Robert N. Rapp, declined to comment. But his client’s record is a case study of how long brokers can stay in business despite years of complaints.

Finra, the industry-funded regulatory group, has recently signaled that it would be taking a harder line to protect the public from such bad actors. It announced last week that it had revamped its guidelines. Fines are being increased, and it has recommended more onerous sanctions for fraud or the sale of unsuitable products. But some investor advocates say they are skeptical that Finra will aggressively use the new tools.

Mr. Cicolani’s most recent legal problems crossed the line into criminal behavior. But securities regulators — who bring civil rather than criminal cases — had plenty of warnings before his arrest, and even before he joined his most recent employer.

Clients of Merrill Lynch, where Mr. Cicolani worked from 1991 to 2010 in Akron, Ohio, had named him in more than 60 complaints by the time he left the firm. Merrill paid $12 million in settlements to his customers and kept him on for years after the complaints began to roll in. A Merrill spokesman said that the complaints stemmed from a strategy created by a more senior financial adviser in Ohio and that the firm decided “that it was most appropriate to resolve the claims.”

In 2004, Mr. Cicolani was subject of an inquiry by the New York Stock Exchange over his handling of “numerous customer accounts” at Merrill, according to regulatory records, but wasn’t sanctioned.

Many of Mr. Cicolani’s more recent victims are left wondering why it took authorities so long to reach this point.

Among them is Ralph Younkin, a retired family doctor who had a 22-year relationship with Mr. Cicolani. In spring of 2014, an F.B.I. representative called Dr. Younkin to let him know that his money — more than $1 million — was probably gone.

“It floored me because I always have trusted my brokers and their guidance,” said Dr. Younkin, an 83-year-old resident of Naples, Fla. “It was almost impossible to believe he would have done that to me.”

In his answer to a complaint against Merrill Lynch, PrimeSolutions and Mr. Cicolani filed with Finra by Dr. Younkin and 11 other investors, Mr. Cicolani denied the claims and declined to answer them based on his protection under the Fifth Amendment.

To Jacob H. Zamansky, a New York lawyer who began filing cases against Mr. Cicolani 13 years ago, news of the criminal charges filed in April came as no surprise. “Given his history with investors, the regulators should have taken disciplinary action long ago,” he said.

It was only after another Merrill customer, Karla Barkett, complained in 2010 that Mr. Cicolani had used more than $1 million of her money for loans and collateral to finance real estate transactions — without Merrill’s knowledge — that Merrill began an investigation. Mr. Cicolani resigned and moved to PrimeSolutions.

Finra opened an inquiry into that case, which Merrill settled for $625,000 in June of 2012. Two months later, Finra concluded its inquiry with a “cautionary letter” but no sanctions.

William Halldin, a Merrill spokesman, did not address why Merrill Lynch kept Mr. Cicolani on after so many complaints. He said that after an “extensive review,” the firm decided it was appropriate to resolve the claims from the early 2000s.

Dr. Younkin and his fellow claimants contend that Merrill had a duty to let them know about the broker’s history when he took their accounts with him to PrimeSolutions. In papers filed with Finra, Merrill said it had fulfilled its obligation to inform the public by filing disclosures to Finra, which put the details into Mr. Cicolani’s public record.

Mr. Cicolani has been barred from the industry, but lawyers and investor advocates say it remains an arduous process to drive bad brokers out.

Robert Pearl, a lawyer in Naples, is representing Dr. Younkin and the other 11 investors, including a retired nurse and her husband; a couple who run a sign business in Wooster, Ohio; and a hairdresser.

“They left Cicolani to prey on an unsuspecting public,” Mr. Pearl said. “Regulators need to crack down on repeat offenders and the firms that protect them.”

In an email statement, Michelle Ong, a Finra spokeswoman, said: “In retrospect, we regret that we did not bring a formal action against Mr. Cicolani earlier.” Finra has refocused its resources over the last two years to aggressively pursue repeat offenders, she said.

In Mr. Cicolani’s case, PrimeSolutions pointed out that regulators had not taken any tough action before the firm hired him.

“Although investigated by the New York Stock Exchange, he was not sanctioned by them or any self-regulatory agency,” PrimeSolutions said in its written answer to the Finra arbitration complaint filed by Dr. Younkin. And the broker “received only a letter of caution from Finra,” it said.

The firm also said it had put Mr. Cicolani under heightened supervision for his first year and had a licensed administrator in the office keep an eye on him even after the year was up.

Other brokers and their firms have faced multiple disputes as well with few serious repercussions. For instance, Oppenheimer & Company, a midsize firm, has 73 regulatory events on its record, 10 of which have been resolved in the last two years. In March, it paid $3.75 million to Finra for failing to supervise a former broker, Mark Hotton, who had 25 complaints on his record when he was barred in 2013.

An Oppenheimer spokesman, Dmitriy Ioselevich, said that in light of recent regulatory actions, the firm had “significantly reviewed and enhanced its policies regarding hiring and supervision of brokers.”

Timothy J. Dennin, a lawyer based in Northport, N.Y., who represented investors who sued Oppenheimer and Mr. Hotton, said that new rules would not make a difference when regulators were not enforcing the ones that already exist.

Although Finra has a complaint database called BrokerCheck, many average customers are unaware of it. Margie Dennison, a 48-year-old hairdresser in Mansfield, Ohio, said that after her husband died in 2013, Mr. Cicolani persuaded her to invest $50,000 in life insurance proceeds in what ended up being part of a Ponzi scheme.

Mrs. Dennison said she had never heard of Finra’s online tool for checking a broker’s record and wasn’t aware that regulators were responsible for supervising brokers until after she had lost her money and hired a lawyer.

Instead, she said, she did what so many investors do when looking for a broker: She asked people in her community who knew him, and invested with Mr. Cicolani based on their recommendations.

“I am not wise about these things,” she said. “I do hair, so you can ask me about hair because that’s my specialty.”

Even knowing now that Finra is supposed to monitor brokers’ activities, she said she was not impressed by the organization’s track record. “Obviously,” she said, “they’ve done a horrible job.”

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A version of this article appears in print on May 19, 2015, on page B1 of the New York edition with the headline: 69 Red Flags Catch Up to a Broker.