You're probably right when it comes to Cain, Buxton, and Kiermeier. Thy're not going anywhere. Billy Hamilton? Uninspiring hitter, but easy to get. Currently he is on the Braves' bench awaiting pinch runner duty. As they are loaded in the OF, he is unlikely to play much defense, but he certainly is good out there. Pillar was acquired for peanuts by the Giants. He makes about $3mill less than Bradley and has one fianl arb year left. The contract-laden Giants might look for any chance to drop payroll, and their price for him was Derek Law and Alen Henson. That would be like to Sox giving up Hembree and Tzu-Wei Lin. Lagares and Maybin will be free agents. There will be options.
Whether or not JBJ is anyone's favorite player, the bottom line is Mookie is irreplaceable. I can nominate CFs to replace JBJ, and at the very least, people will argue, with some agreeing and some disagreeing. I can't think of a RF where we can have that same type of argument with Betts. There just isn't anyone. So if the Sox need to keep either player, the choice at which one you try to keep is obvious to me. Bradley is probably th safer answr, as he should be much easier. Although it's not like he has been all over taking an extension, either. And his agent isn't known for hometown discounts.
Yeah it feels like dealing Lynn to California in some ways.
But even if the Sox tender Bradley, his agent is Scott Boras. So if you tender him and guarantee Betts leaves, all you're doing is increasing the odds that both leave after 2020 anyway.
The biggest reason is the Luxury Tax. Say Bradley gets his $10-12mill. That doesn't mean he costs the Sox $10-12 mill. Depending on final payroll, that could be as high as $14.5mill to $16.8mill. My thoughts were that Bradley just isn't a $10-12mill player. Do you think he is a $15-17mill player? That's what Henry would be paying. If the Sox bring back Betts and Bradley, the amount the Sox pay Bradley plus his luxury tax hit could be nearly 70% of what Sox actually pay Betts. (Assuming $25mill for Betts here.) That's not insurance; that's a drastically disproportionate pricing scheme.
Bradley does make baseball sense. He's a good player. But the financial impact does matter, too. A lot of these decisions have to transcend baseball quite often. It is a business after all...