Odd thing about that picture. While the board is the right way round, the Blue pieces are at the wrong angle for the game. Not that it matters much given that the Red side is cheating hugely by adding three extra boards filled with 16 faceless pawns which is twice as many as is legally allowed. In addition, a large percentage of those pawns aren't actually on squares but are on the intersections instead, which is illegal.
Of course, being unable to move vertically means that they are unable to reach the main board, unless they turn into suicide attacks (damaged from throwing themselves over the edge... hmmmm, an interesting potential metaphor there...)
The two primary pieces on Red (King and Queen/Trump and Whatsername) seem to be taking up twice as much space as is allowed, having a 2x1 base rather than 1x1. While the Blue side has four counters, it is not uncommon for Pawns to be denoted by Draughts/Checkers counters due to how easy it is to lose the pieces in question. Nevertheless, that particular representation is... borderline. Given the orientation of the blue pieces, the four counters at what at first glance appears to be the first row (where Pawns cannot be due to how they move), it is possible that the CNN counter is about to get promoted, probably to a Queen. In addition, the blue knight seems well positioned to take out the K-Bishop which is currently totally unprotected. It is also worth noting that unless Trump is a Queen, the fact that Blue is moving one of the counter/pawns indicates that the Obama-piece is a piece that has a far wider range of movement than Trump, given the fact that Whatsername is on the same diagonal and it would otherwise be check, forcing Blue to move Obama or block the potential attack.
My conclusion? The person who drew the cartoon knows about Chess only from watching Star Trek.
The intended metaphor has failed under scrutiny.
Which is, in itself, another metaphor...