One view is he got lucky by selling broadcast.com for billions when ultimately it would be worthless. Another view is that it is extremely shrewd to sell at a high price.
He had to take the deal. He couldn’t make it huge like Yahoo could have (but failed). And yeah it had some buzz and Yahoo paid in stock so it didn’t really cost them much - just their own paper. (Cuban hedged his stock too, so didn’t lose if/when Yahoo stock fell apart).
But as MR said, there may be more to the story. These tech finance people are very influential. Not just politics but also with selling great deals for their benefit.