Let's say that you are Dave Dombrowski. You and Sam Kennedy are the bosses of the Boston Red Sox. Sam takes care of the business side of the operation, which are extensive, complicated, and require great skill and long hours, while you, Mr. Dombrowski, handle the baseball operations. Here's what it adds up to -- Sam is in charge of making the money and you are in charge of spending it.

Oh, we should also mention that, boss that you may be, you have bosses too. They are John Henry and Tom Werner and their partners, the owners of the team, the guys whose money you spend.

You are blessed in that Sam does his job really well and that your bosses have deep pockets, really deep pockets. And they love baseball. They are also very smart guys. How else do you suppose they got to accumulate all that dough in the first place? They have entrusted you to spend it wisely. They, like you, are committed to winning; and they pay close attention.

Red Sox Nation, the fan base, is focused on closing out the 2018 season successfully and winning in the post season, but as the boss you already have to be looking ahead to the off-season and planning for 2019 and beyond.

One issue that must be faced is Craig Kimbrel's pending free agency. Last year he was absolutely lights out as the Red Sox closer. This year there has been some drop-off, but he's still been pretty good. He's making 13 million bucks this year but chances are that he'll be looking for a deal comparable to the one Aroldis Chapman landed with the Yankees, $17.5 million a year for five years. That's a total of $87.5 million, not all that much for a front-line starter but a new frontier for someone who only pitches an inning or so at a time. What do you recommend to your bosses? That they let Kimbrel walk rather than pay him all that money? If so, how do you replace him and with whom? What if he turns out to last a long time as an effective closer, pitching for some other team? And what if it's for a team like Cleveland or Houston, a real contender, in other words, the competition? Of course, you could recommend that the Sox resign him. But that would require a multi-year commitment, and what if Kimbel's drop-off this year is just a forerunner of what happens next year and the year after that? My God, we're still paying Aroldis Chapman kind of money to Pablo Sandoval. Don't think that has slipped the mind of your bosses. It's your call, Mr. Dombrowski, and remember, the bosses are keeping score, and they know how to add.

While we're at it, what about David Price? He can opt out of his contract after this season, a contract that calls for him to be paid $31 million next year and $32 million for each of the following three seasons. That's a lot of dough. Conventional wisdom has it that he could never command that kind of money anywhere else because he's been spotty thus far in his Red Sox career, but ever since the all-star break he's been terrific, one of baseball's best pitchers. Whether to stay or go is Price's decision to make, and leaving would be a big roll of the dice for him. The ballclub and its attitude toward him can be a big factor in what he decides. What do you encourage him to do?

If you look ahead to the off-season after 2019 it gets really interesting -- and more than a little frightening. Chis Sale will be eligible to become a free agent and J.D. Martinez can opt out of his contract. I suppose, Mr. Dombrowski, that you're already busily at work trying to work out contract extensions for both of them before they hit free agency. I also suppose that there are people around them who want them to test the market, which, provided that they stay healthy, should mean barrels of money for them and their families. Sale is the best bargain in baseball right now. He makes $12.5 million this year, and that goes up to $15 million in 2019. On the open market he would get more than double that. Do you commit to paying him $35 to $40 million a year for multiple years, say, six or seven? You have to assume that the Yankees would if they had the chance. Is a bidding war between you and the Evil Empire in the stars?

J.D. Martinez could win the Triple Crown this year. If, in 2019, he has a another year anything like this he'll certainly opt out of his current deal, which will pay him $23.7 next year. Someone -- maybe the Red Sox, maybe not -- will be paying him telephone numbers kind of money after 2019. What do you recommend to your bosses?

I hate to even think about the off-season after 2020 when Mookie Betts and Xander Bogaerts, both still young players, will be eligible for free agency. You, however, as the boss of baseball operations, have to think about it. There are all kinds of other spending issues -- including other contracts -- to worry about, to say nothing of payroll taxes. But the pending contracts of just four players: Sales, J.D. Martinez, Betts, and Bogaerts, will likely add up to more than half a billion dollars. A hundred million here, a hundred million there, pretty soon you're talking about serious money, you know what I'm sayin'?

Can you sign them all? If not, which ones do you let walk? Your bosses are keeping a close eye, not only on what's being spent but also on what the results on the field will be. You've got some big decisions to make, Dave, and, unlike those of us who'll be second guessing, you'll be held accountable.

Good luck to you and the Boston Red Sox.



- Dick Flavin is a New York Times bestselling author; the Boston Red Sox “Poet Laureate” and The Pilot’s recently minted Sports’ columnist.