I heard somewhere we were just barely over the $40M mark this year. My guess is the official number will show we ended up just under the $40M over line. That might be evidence that the Boston bean counters are hard at work trying to keep us under that top line. The draft penalty is not severe, and if you go just barely over the tax on a small amount over is very small, so in that sense going over the $40M line in and of itself is not earth-shattering, but going over by a lot may take its toll.
My guess is DD is not being forced to stay under the $40M line, but it is a high priority not to go way over it. My guess is, upper management has already chosen a season where they plan to reset. I think it will be the 2021 season, so any new contract that runs through 2021 will be very carefully scrutinized with that in mind, and the fact that any 2021 salaries on the books may prevent re-signing some of our best young stars.
At some point, it will likely become a juggling act for DD. I'm not calling out anyone who thinks Henry will just keep sending and spending through 2021 and beyond, but re-setting the tax for just one year would save Henry a ton of money for many years afterwards. I'm thinking that is the plan, and my suggestions and projections are based on that foundational belief.