I agree, celebrating Tubman's life by putting her on the $20 to replace Jackson is somewhat disparaging to Jackson in itself. Webb's point was about more than who is on the bill, though. I can live with Tubman replacing Jackson on the $20 - she's worthy of such a high honor - what bothers me is the public and the media unceremoniously tossing out one of America's most important historical leaders and stomping on his legacy.
Nobody is disputing that Jackson was an important figure - in fact, if they didn't think he mattered, why waste the time trying to slander him? The issue is that Jackson's legacy was extremely harmful and should not be celebrated. Was Joseph Stalin not an extremely important historical figure? Does that mean we should honor him? Obviously not.
This claim is absurd. Jackson very much was not in favor of the people at the bottom having any sort of power, otherwise he wouldn't have owned so many of them. Even ignoring that, what exactly did Jackson do for democracy? Supporting universal white male suffrage? A pretty empty gesture given most states already had that by the time he was sworn in, and, as MOP already mentioned, basing suffrage on race is hardly a step up from basing it on property ownership. I'd argue it's actually a step backwards, and served to divide the lower classes, further empowering aristocrats like Jackson. Now, you have two groups who should have similar interests, poor whites and poor blacks, at each other throats instead of against the people who are actually oppressing them. Not to mention, the policies he did pursue very much made life worse for the "common man" he claimed to represent. Killing the bank? Great symbolic gesture! Or at least, it would have been if it didn't plunge the economy into a depression and led the masses to starve. Oops. And of course, there was his commitment to upholding the institution of slavery, killing social mobility and keeping the poor white class poor. But hey, at least he let them vote for him!
It's hardly "anachronistic." Jackson had these criticisms thrown at him when he was alive. Turns out the idea that genocide is morally wrong isn't as novel as most people seem to think.