Brewer Samuel Smith and its chairman have been fined almost £28,000 for failing to provide pension information to regulators.
The Pensions Regulator focused on the pub chain and Humphrey Smith in 2015 to make sure it was earning enough money to support its pension schemes.
Both admitted neglecting or refusing to provide information and documents.
At Brighton Magistrates’ Court on Monday, Smith, 73, was fined £8,000 and the brewery £18,750.
They were also ordered to pay a total between them of £1,240 in costs and victim surcharges.
Criminal proceedings were brought against the Tadcaster company, which was established in 1758, after it failed to meet a 26 January deadline for providing the relevant information, the regulator said.
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Smith was charged because the offence by the company was committed with his consent, connivance or neglect, the pensions watchdog said.
In May, both the company and Smith pleaded guilty to neglecting or refusing to provide information and documents without a reasonable excuse under the Pensions Act 2004, the regulator said.
The company, more commonly known as Sam Smith’s, provided the necessary details several months later but criminal proceedings had already been launched, it added.
It is said to be Yorkshire’s oldest brewery and operates around 200 pubs across the UK.