Betts dilemma will dominate Boston's winter

November 12th, 2019

One of the greatest free-agent contracts in history, and maybe the greatest ever for the Red Sox in terms of value, was the one for . After the 2000 season, they signed Ramirez for eight years and $160 million, and then something quite rare happened: Ramirez’s numbers for the duration of that contract were remarkably similar to the ones he had put up with the Indians, numbers that made him that big-dollar signing for the Sox. It hardly ever happens that way.

You know what happened with Ramirez, who was 29 years old at the time, after he got the money. He and became the kind of lefty-righty 1-2 punch that Fred Lynn and Jim Rice had once been -- only better, and more important. In 2004, the Red Sox won their first World Series since 1918, then won another in ‘07. If the Red Sox had known Ramirez was going to help them do that, they would have paid him even more than they did. Though what he meant to their fan base and to their brand would be almost impossible to quantify.

Now, all this time later, and a year after helped them win another World Series in 2018, the Red Sox have another financial decision to make. They will have to decide whether to give Betts a contract that could be worth twice the one they gave Ramirez nearly two decades ago.

Betts, still just 27, isn’t a free agent yet. That doesn’t happen until next winter. If he goes to salary arbitration this year, he is expected to earn close to $30 million for the 2020 season. The problem, of course, as Boston fans know and baseball knows and people in outer space know, is that the club’s executives have said they would like to bring the team’s payroll -- currently estimated to be in the $235 million range -- below the $208 million Competitive Balance Tax threshold. In the short run, it is as much a mandate for Chaim Bloom, the new head of baseball operations, as winning another Series.

And when you look at the Red Sox's finances and where their payroll is, you can only come to this conclusion: If Betts stays, for this year and for much longer, then someone else with a big salary has to go.

The first name that comes to mind is David Price, who is set to make $32 million in each of the next three years. Of course, to make that work, Boston might have to include some prospects in a deal, or eat some of the salary, since Price no longer pitches like the ace he was when he earned that deal. Maybe they could trade J.D. Martinez ($23.75 million salary in 2020), who just opted back in to at least another year with the Red Sox. But in the current economic climate of the sport, you have to believe it would be a lot easier to move a pitcher like Price than a designated hitter, even one who has been as wildly productive as Martinez.

We are once again reminded just how fast things can change in baseball, because a year ago, the Red Sox were cleaning up the streets of downtown Boston after another Duck Boat/World Series parade.

I personally think the Red Sox would be nuts to trade Betts. He won the 2018 AL Most Valuable Player Award -- in a season where he out-Trouted Mike Trout -- and finished second to Trout in '16. He is not as popular as Ortiz was in Boston -- no one may ever be again -- but he could be on his way (if he stays). If you add it all up, he is as gifted an all-around player as the Sox have ever had. Buck Showalter told me once that Betts is the best right fielder he’s ever seen with his own eyes, playing as tough a right field as there is in the sport.

More importantly, Betts has shown he can thrive in what can be a claustrophobic market for sports stars, especially those as big as Betts has become in Boston. Right now, the only bigger star in town is Tom Brady.

The Red Sox have made at least one big offer to Betts, after the 2017 season, north of $200 million for eight years. He elected to wait -- to take the “emotion” out of the decision, as he said at the time and keeps saying. Now the money has only gone up, in light of what Trout got from the Angels, the $330 million Bryce Harper got from the Phillies and the $300 million Manny Machado got from Padres.

There is one thought, coming from people quite familiar with the Red Sox’s thinking, that they might still offer Betts a seven- or eight-year contract worth enough money that the annual average value of it might allow Betts to set a record there. But he’s not going to get Trout money. As gifted as he is, as good a guy as he is and as good a teammate, he’s not Trout. Nobody is.

Once, a long time ago, Ramirez was worth the money. Not just because of what he’d done already, but what he was about to do in Boston. Ramirez didn’t finish his career at Fenway. Betts should. But always remember the wisdom of a great old football man named George Young on the subject: "When they say it’s not about the money, it almost always is."

“It’s kind of a remarkable situation,” someone quite familiar with Betts’ thinking told me the other day. “They’d like to keep him. He’d like to stay. But he still may end up going. How crazy is that?”

Not crazy. Just baseball. And business.