He will have his guaranteed money, but how long will he be the highest paid. Top salaries may finally be leveling off after decades of out of control proliferation, but I thought that Rickey Henderson, to name one example, once slid from first to fifty-fifth in salary in less than three years. Salaries were rocketing skyward like crazy when Henderson was in his prime.
The other extreme, that came up in another post, is to bet on yourself every year. One year for present performance. That's how Michael Jordan did it almost his entire prime. Scottie Pippen, as a young player in 1989 before the dynasty began, went for the safety and security of the long term deal. For a brief time he was making more money, on the court, than Jordan. He wouldn't for long. By the mid point of Pippen's contract he was getting chump change compared to his value. Reinsdorf and Krause never let him out of his original deal, never renegotiated. Pippen was furious for a long time, even when he was winning rings.