Now, the multimillionaire is going all-in on a battle with the very industry where he cut his teeth - the gambling sector.
Webb has beaten the house before, having provided financial backing for the successful campaign to restrict £100-a-spin fixed odds betting terminals (FOBTs). This time, the stakes are high, the up to £3bn a year in duty the gambling industry pays to the exchequer.
As the Guardian reveals today, Treasury officials are considering proposals to double the taxes levied on parts of the sector, as the chancellor, Rachel Reeves, seeks to pull every lever possible to raise funds in her budget on 30 October.
The industry, which takes in £11bn from British punters every year, is putting up resistance, warning of the twin spectres of the hidden market and potential economic damage to a sector that claims to support 110,000 jobs.
Historically, gambling is an industry that has wielded influence with Labour, thanks in part to donations worth more than £400,000 since 2020, some of it to Reeves's own office.
But Webb has blown that figure out of the water, quietly becoming Labour's fifth-largest individual donor since the beginning of 2023 by channelling £1.3m of his money into the party.
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