> It's hard to imagine he would incentivize Pelosi to pass an aid bill just so he can block it, what is the political upside for him if he does that?

If it looks like it doesn't have a chance of passing anyway, it provides an opportunity to publicly rebuke the other party. He pushed through AoC's Green New Deal with a smirk [1].

[1] https://www.cnbc.com/2019/03/26/aocs-green-new-deal-dies-in-...