Great post and it highlights the irony of the Machado negotiations.
The Sox FO claims they had the better offer and were surprised he would go for the higher guaranteed contract. It's exactly what Jerry did with the Sox.
Sure you could get more money by putting a competitive team on the field, but why try when you are rolling in cash already? He bought the team for what, 50 million? It's worth over a billion today. Why would he care?