The angle here for the Casino is painfully obvious. Host a money match, and give the winner 5K. So it's not horribly imbalanced, make it an iron-man deal, with several games being played. USFIV, SFV, SFVI and maybe Tekken 8, Soulcalibur VI and Smash, Ft3 on each, winner takes all. I've no doubt in my mind that Phil will absolutely refuse, but he already looks like shit by doing so and going "Let's hit us sum goals so I can stuff my face with fast food, guizeee!"
Much like the Keemstar thing. You can't really beg if you're getting spectacular business oportunities and noping every one, no matter if your obese mo-wife is against it on a matter of morals and principles. 50K is very much lifechanging money and Phil felt completely comfortable saying no to that on the grounds that Keemstar's business model is immoral, harmful and wretched or some other boomer shit. Misery Merchandising Incorporated. Having a good day because someone else is having a bad day. As opposed to the ball of sunshine and kittens that is Burnell Productions, of course.
Making the fight into an event is much better than just handing the money to LTG. Plus, it'd make them actually fight for it. Otherwise whoever starts losing is just gonna make an excuse and roll over to avoid humilliation. If only the winner takes the bag home, they both would have to bring their A game, C- as it is in both cases. I suppose LTG would okay that, too. To be fair, running scared from DSP of all people with 5K on the line would make him look like a massive bitch. I don't think it'd take much to fold the pigroach into a pretzel, he really is just a flowchart warrior.
Hell, if LTG bitches out anyway, offer it to Brian. Phil will nope that shit with the quickness, and Brian will be mighty pissed at Phil. Blowing an opportunity for five bands without even considering. After all, the dents give him twice that monthly... Why should he get off his ass? Other than because of this weird one-sided rivalry he's got going with the Cannon brothers, or to deepthroat Sir JWong's dick as he's getting viciously, hopelessly curbstomped.