Amazon took a million-dollar gamble this week, betting a last-minute cash infusion will help elect a new Seattle City Council despite the inevitable backlash to the contribution. It's a risky move that has already emboldened Amazon's biggest critics in Seattle government. Whether the bet will pay off at the polls remains to be seen.

Also on this episode: 

• Andrew Yang’s Bing ding creates a debate of its own over Microsoft, Google and tech history
• An employee on Microsoft’s board? Shareholder proposal floats concept, board calls it ‘unnecessary’
• Benioff: Amazon’s Seattle tax fight stoked tech industry opposition to S.F. homeless initiative
• Breach the Bubble: Meet a Former Democrat Turned Trump Voter