Mr. Rich’s pattern of donations, while unusual, is emblematic of an openly money-focused political culture in Albany in which lobbyists crowd fund-raisers for elected officials steps away from the Capitol, and trade associations pour contributions into campaigns.

Mr. Rich said that his donations were personal and had no connection to his job.

“My personal contributions are mine alone and reflect my passion for, and participation in, the political process,” Mr. Rich said in an email.

But seven candidates who have received checks from Mr. Rich in recent years said they assumed the checks represented donations from the association, rather than expressing Mr. Rich’s personal political beliefs. That the checks came from his personal account caused some confusion.

“I always wondered about that,” said a state senator, who, like other candidates and elected officials who spoke to The Times, requested anonymity to discuss Mr. Rich’s contributions for fear of antagonizing a major contributor. “It’s an unusual arrangement, even in Albany.”

Employers are barred from paying their workers extra compensation with the expectation that the money would be used for political contributions, said Henry Berger, a veteran election lawyer. “If anybody could ever prove that such an arrangement was made, it would be found illegal,” he said.

Mr. Rich said that no such arrangement existed.

“No part of my compensation is determined by or connected to my campaign contributions,” he said. “In my 26 years at G.N.Y.H.A., I have never been directed or required by my employer to make a campaign contribution, nor have I ever been reimbursed by my employer for a campaign contribution.”

Other major trade associations do not pay nearly as much, even to their top officials. John Banks, then the president of the Real Estate Board of New York, which represents developers’ interests, was paid about half as much as Mr. Rich in 2017.