There will be a different lawyer, a sharper presentation, and I imagine it will be well-woven. I may not care for Trump at all, but that man does not like to lose at anything.
They can be bought, yes, they also have billions each to buy others with. Like some dirty lawyer(s) who does know what they're doing and that goes right back to Synonym's point.
Maybe, but I kinda doubt he can buy it. First of all, very few lawyers are admitted to argue before the SCOTUS, and federal interests are argued by the Solicitor General. Trump hasn't appointed one. The original orders, from what I've heard, were drawn up by his corporate lawyers. Constitutional Law is a specialty unto itself. You can't just whip something together. Also, he just hasn't hired enough attorneys to fill the Justice Department to argue his case effectively, he won't/doesn't want to use Obama-hires, and he's absolutely NOT using his own money. He's all about skimming, not spending his own.
He simply can't go lawyer-shopping for the federal government the way he can for his fights with Scottish cattlemen. Beyond that, he doesn't exactly run with the creme de la creme of legal scholars, just the thuggish contract and corporate specialists. The really high-powered ConLaw specialists will think long and hard about associating with his government. He requires soul-selling as the price of a job.
Now, he's certainly within his rights to craft a policy on immigration. Obama did it. He slowed refugee admissions to a crawl while they retooled the vetting. It simply has to be done withing the bounds of the Constitution. It can be done. He can "win," but it'll have to be with a significantly revised EO. What he risks is his base saying he's gone "soft" on the issue, and I imagine that probably preys on him some. He wants to have his cake and eat it, too, but I'm not sure that's really possible at this point with respect to this EO. He might have to be satisfied with licking the frosting. (Ew, a nauseating image, sorry.)