I recall posting about this quite a while back when the aviation defendants brought a partial motion for summary judgment, to ask the judge to limit Mr. Silverstein's claims against them to the market value of Mr. Silverstein's leasehold interests in 1WTC, 2WTC, 4WTC and 5WTC, rather than the replacement cost of those buildings. The judge granted that motion and held that the
aviation defendants could only be held liable for $2.805 billion back in December 2008 and they later addressed the future possibility of set-off etc., some time around September 2009, since other courts had determined that the multiple insurers were liable up to $4.55 billion.
I can't remember whether the December 2008 and September 2009 decisions were appealed or anything, but I thought that the litigation had since settled. I'm not entirely sure, though, so I'll look into it further.
I do know that of the 21 property damage plaintiffs (including, collectively, the WTCP plaintiffs - i.e., Mr. Silverstein's entities), 18 of them settled for $1.2 billion after mediation in late 2009 and the settlement was approved in July of 2010 (that's also in the link that AJM posted), which left just the WTCP plaintiffs, Cantor Fitzgerald, and a company called Cedar & Washington Associates that owned 130 Cedar Street. Cedar & Washington's claim was dismissed in September 2010, and Cantor Fitzgerald's claims were limited by another decision of Judge Hellerstein some time last year, and I think that's the only property damage claim against the aviation defendants that hasn't been resolved.

I'm not entirely sure (see above) but I'll see what more I can find out.
The courts did not "award" Mr. Silverstein $4.55 billion as RedIbis claims. Rather, the courts told the insurers that they were liable
up to a maximum of $4.55 billion, subject as always to proper evidence of proof of insured losses in accordance with the terms of the insurance policies.
Those judicial decisions do not end the matter and certainly do not mean that the insurers all pulled out their chequebooks immediately to pay out their policy limits to Mr. Silverstein. As I recall, some of the smaller insurers paid out pretty quickly after the litigation was final because it was obvious that their policy limits were reached very quickly, but the actual payment of the totality of the insurance money is subject to all manner of conditions and evidence of actual insured losses and the happening of various events.
I haven't seen any evidence at all to support the allegation that Mr. Silverstein "made out like a bandit".