Before we get to whatever it is that President Trump is on about, here, here is something that happens to be true: by many measures, Colin Kaepernick is a more prolific philanthropist than Donald Trump. Trump has always been happy to play a philanthropist in public, as part of his broader role as Public Rich Guy. At times this has meant bum-rushing the stage at charity events to which he was not invited, for charities to which he had never given any money. It has meant using other people's money to do things like settle his debts or buy a bizarre Pie-O-My-grade portrait of himself and donate it to one of his residences. It has meant a great deal of bombastic promises to donate to various vague but worthy causes.
But, as the Washington Post's David Fahrenthold demonstrated during the campaign, it mostly hasn't amounted to much in the way of actual verifiable charitable donation. Until Trump finally donated a million dollars—his much-vaunted personal contribution to a campaign-season fundraiser for veterans charities—last year, Fahrenthold struggled to find just about any substantial donation from Trump between 2009 and 2016. He did even that under great and salty duress; the money arrived in one chunk, directed to a charity called the Marine Corps Law Enforcement Foundation. It's unimportant, but appropriately hermetically Trumpish, that the organization's founder served in Iraq with the son of Trump's bodyguard. Trump claims that he does a great deal of charitable giving, and does so in uncharacteristic and inexplicable secret; his unwillingness to release his tax returns makes this difficult to verify, and Fahrenthold's exhaustive attempts to verify any of Trump's touted donations turned up strikingly little in the way of actual giving, whether in terms of Trump's own money or the outside funds he controlled through his inevitably eponymous foundation.
By means of contrast, Kaepernick pledged last fall to donate $1 million of his salary, plus all the royalties he receives from his jersey sales, to various charities, with $100,000 going out each month for ten months, in variously sized chunks; Kaepernick's website enumerates the amount each charity receives, and offers a brief explanation as to why that charity was chosen. In 2017, at least, he has donated far more money than Trump, who once again promised a number of donations—of his $400,000 salary, of the leftover money from the $90 million raised for his inauguration events—and has once again been unable or unwilling to supply anything like receipts. Due to a campaign fundraising blooper related to an FEC rule against anonymous gifts in excess of $50, Trump's campaign did donate $450 to the American Red Cross. "A far as I can tell, that's the only verified donation *to charity* from anybody connected to Trump," Fahrenthold told me via email. "Trump personally gave some money to a guy who came to his inauguration, which the Post wrote about; Justin Jouvenal was the writer. But that was to a guy, not to a charity."
Trump also hasn't done any of the sort of signal-boosting that Kaepernick has, most recently for a charitable effort to bring relief supplies to famine-stricken Somalia. Trump did put Somalia on the list of restricted countries in each of his court-suspended travel bans, but maybe we can otherwise cut him a break on this. He's been busy. Being President.
Look, everything about Trump that is stuck or rusted-shut or broken in 2017 was also that way about him in 1987, and 1997. If there had been a Colin Kaepernick for Trump to jeer when he was at his zenith or his gilded rock bottom, he would have done it. It's clear that Trump is gloating in the sequence above from his rally, although it's obscured some by that channel-flipping way in which he constantly remembers and notes new outrages against himself. It's not exactly clear what he's gloating about where Kaepernick is concerned, though.
Some of it is easy to understand, admittedly. Trump clearly believes that the threat of a salty tweet at 6:41am on a Saturday is keeping Colin Kaepernick from signing a free agent deal with a NFL team; it's a throwaway line in Mike Freeman's Bleacher Report piece about Kaepernick's current professional purgatory, but by now we know that Trump reads everything in perpetual "ctrl-f Trump" mode. It seems clear that Trump believes this to be an achievement of some kind. It seems like a reach to read that as Trump claiming a victory for the national anthem and traditional values over the left-wing afro-wearing protest guy, if only because the Occam's Razor answer for Trump is always to assume that he's talking about Trump. He almost always is.
But even if the central purpose of Trump's drive-by was probably something along the lines of "I do very popular posts online, folks," there's also more at work here. What Trump gets as a politician is something that he got decades ago, back when he was just an extremely public citizen wheedling for a few minutes of mindshare. He performs this knowledge daily: that repeatedly smashing any bright-red cultural button is a great way to get a treat, or at least a mention in a tabloid newspaper. Kaepernick has been an electrifying NFL player, but he is now into the Totem/Symbol period of his career; Trump was once (if briefly) an actual successful real estate developer, but he also long ago became a similarly symbolic figure himself, a big soft plum of a metonym for Powerful Rich Guy. They are both, now, just what they represent. If Kaepernick is unemployable in the NFL, it's because he represents the broader contemporary social movement for social justice, not because he is an unreliable pocket passer or whatever. It's because people like the ones Trump is pandering to above understand him as a symbol of things they hate. Trump, who was a meme before anyone even knew what the word meant, understands this. He understands it at the same level, and in the same way, that cats understand their relationship to mice.