In reality, Hal is a very generous owner. I'm sure Pirates fans, Rays fans, and Mets fans would love to have an owner who spends the kind of money that Hal spends on the Yankees. Over the last ten years, you won't find an owner that has spent more money on his team than Hal Steinbrenner, and yet the Yankees haven't made one World Series appearance over the last ten years. Thus, the Yankees don't have an owner problem, they have a GM problem. How much does Hal need to spend before dummy Brian Cashman gets the Yankees into the World Series? Does Hal need to spend 400 million on payroll to make it happen? He has already given Brian Cashman big prizes including G.Cole and yet what has Cashman accomplished over the last ten years?
I would love to see Brian Cashman take over a team that doesn't spend, like the Pirates, Royals, or Rays. Cashman would lose 100 games a year in that setting. The only thing that keeps Brian Cashman above water is Hal's excessive spending.
The last time the Yankees won a World Series title, Hal opened up his wallet for Sabathia, Teixeria, and Burnett. The idea that Hal doesn't spend is ridiculous--he is one of the most generous owners in baseball.