I'm a transactional attorney negotiating real estate and financial deals. In my experience handling complex contracts, each party has a different set of goals and a deal is more complex than just money, and lying doesn't really get you anywhere. You argue for what you want based on logic, not on what someone else is doing, because each party will have goals that they have to work within.
Obviously I don't work in sports, but from my experience, it would work something like this: Machado might accept a total dollar amount of $X, or an average value of $X, plus a minimum number of years, and opt outs at certain times, etc. Each team can give and take within those parameters. So even if a team is offering more total dollars and years, they might get beat by higher annual contract amount plus early opt out. So, the Sox, for example, might not want an early opt and will make up for it with more money and a no-trade clause or something.
It really isn't comparable to a car negotiation. The package each team offers is too complicated to simplify to just money. And the location and competitiveness of an organization could have value to the player as well which is very difficult to monetize.