10. David Glass, Kansas City Royals
Don't let recent success blind you to an ample history deserving of scorn. After running arguably the worst non-arms-manufacturing company in the world, Walmart, Glass became sole owner of the Royals in 2000 and immediately treated baseball the way Walmart treats people.
Amid a jackal pack of ownership that included a (future) commissioner guilty of collusion to fix player salaries, Glass – then the team's president and CEO – stood out as an anti-labor hardliner during the 1994 strike, wanting to bring in scab players for a monstrously un-telegenic spectacle summarizing the kind of fuck-you tactics Glass learned at the Bentonville, Arkansas smile-time sociopathy juggernaut. He simultaneously advocated a hard salary cap in baseball, not to create an even playing field with large-market teams but to have a paper excuse to wave in doubters' faces explaining why he didn't spend anything on his team. Glass went ahead without one, with team payrolls routinely languishing in the bottom half of the league during his tenure, with notable years like 2000 (28th), 2003 (29th), 2005 (29th) and 2011 (30th). That's out of 30. The last two years, Royals payroll has leapt to 19th in the league, but don't let the 2014 World Series run fool you. Fans have every reason to expect them to regress, and every expectation that Glass won't spend to correct that (Goodbye, Billy Butler.) After all, four seasons of 100 losses and an average of 92 losses per season under his tenure is a much bigger sample size.