February 12, 2015 6:03 AM EST

Ethan Czahor was a hiring coup for Jeb Bush’s all-but-certain presidential campaign. The co-founder of Hipster.com offered coding chops and Silicon Valley cred rare among Republican operatives.

But late on Feb. 10, barely 30 hours after TIME had reported Czahor’s appointment as CTO of Bush’s Right to Rise PAC, the tech guru was forced to resign. The surprise divorce came after reporters–with the help of Democratic hands–uncovered old tweets and blog posts from Czahor that were offensive to women and minorities, the very constituencies Bush needs to attract in order to broaden the Republican Party.

The abrupt turnabout on Czahor highlights the GOP’s long-standing trouble recruiting the talent needed to close the tech gap with Democrats. Bush’s team was so eager to get him on board, it neglected to properly vet its star hire.

Part of the problem is cultural. Despite its libertarian economic instincts, Silicon Valley tends to share the social agenda of the Democratic Party. In 2012, President Barack Obama capitalized on that by drawing top engineers from leading tech outfits to build the most sophisticated political-data operation in history. After the GOP’s defeat, the Republican National Committee tried to play catch-up, trumpeting the hiring of former Facebook engineer Andy Barkett as its CTO. Alas, Barkett had trouble navigating the ways of Washington, and he was marginalized before the 2014 election and replaced in January 2015.

–ZEKE J. MILLER

This appears in the February 23, 2015 issue of TIME.

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