Transnet paid Gupta-owned TNA Media more than R140m between 2012 and 2017, the state capture commission of inquiry heard on Tuesday.
The commission, headed by Deputy Chief Justice Raymond Zondo, has been probing allegations of state capture, corruption and fraud at state entities since August 2018.
On Tuesday, the inquiry continued to hear testimony relating to multimillion-rand sponsorship deals for business briefings entered into between the state-owned freight rail, port and pipeline group and The New Age newspaper.
According to an affidavit presented to the commission, Transnet paid R122m between 2012 and 2017 to sponsor dozens of New Age business briefings. It separately paid R24m to The New Age to sponsor the Big Interview, which appeared in print. The briefings were aired on the SABC. State power utility Eskom was also a former sponsor.
The senior manager for Transnet Group Capital, Daniel Kagiso Phatlane, testified he had initially supported sponsoring the business breakfast briefings, saying he saw them as a means to boost Transnet's brand while also promoting "discourse and discussions around what is happening in our country".
Transnet would pay in the region of R20m per year to sponsor about 20 business breakfasts. The sponsorship meant its logo would be displayed during the breakfast, among other perks.
Phatlane said by 2014, however, he started having second thoughts and feared sponsoring the briefings might have started to harm the Transnet brand.
"It was as if we were just dishing [the R20m per year] out."
Phatlane testified that, by about 2014, he and some of his colleagues felt Transnet should be "scaling down or cancelling" the sponsorships. But he said he did not have the power to make that decision.
The business breakfast sponsorship deal ended in 2017. The newspaper, later rebranded Afro Voice, shut in 2018.