Next winter Machado will hit the free agent market at the age of 26. Given his talent and how young he’ll be compared to your typical star free agent, we can expect he’ll be seeking a lucrative long-term deal that could go as high as $300 million.
Is he worth that type of mega-deal? Probably, although that’s an argument for another day given that it has little relevance to the decision to trade for him now. Boston’s chances to ink to him a massive deal next year are about the same as any contender with that much money to spend regardless of if they can bring him here a year early.
Sure, giving Machado a one-year trial run in Boston could give the Red Sox a better chance to sell him on the city, the organization and their passionate fan base. Perhaps that gives them a leg up in negotiations a year from now. Is it really worth giving up a massive haul in a trade now to find out?
Let’s be honest – there is zero chance that a Machado trade will be contingent on him signing an extension with the Red Sox. While Boston’s brass may push for that option, what incentive does Machado have to agree to that? It’s one thing for a player to show loyalty to the organization they broke into the big leagues with by signing a below-market extension. Why would Machado feel inclined to pass up a potentially bigger payday as a free agent by showing that same loyalty to a team he is being traded to?
If the Red Sox trade for Machado it will be a one-year rental with perhaps a slightly increased chance of convincing him to stay once he’s had a taste of the atmosphere here in Boston. Granted, that could backfire if Machado decides he doesn’t like it here. He certainly wouldn’t be the first star player to feel that way.