Musings: Enjoy Yourself, It's Later Than You Think

By Dick Flavin

Boston Red Sox Poet Laureate

and New York Times Best Selling Author


If you are the Boston Red Sox, the chances are that the player you most want to keep on

your roster for an extended period of time is Mookie Betts. And who could blame you?

He was the American Leage MVP last year, won the batting title with a .346 average,

was a 30-30 man with 30 stolen bases and 32 home runs, and collected his third

consecutive Gold Glove award.

If, on the other hand, you are Mookie Betts, the chances are that you’ll want to test the

free agent market once you become eligible after the 2020 season. And you couldn’t

blame, either. After all, Manny Machado has signed a ten year deal with the San Diego

Padres worth $300 million, an all-time record. Just a week later Bryce Harper put his

name on a thirteen year contract with the Philadelphia Phillies that pays him $330

million, topping Machado’s record.

Here is the truth: Mookie is demonstrably better than either one of those guys.

Harper, for example, batted just .249 last year. That’s ninety-seven points lower than

Mookie’s average. His defensive metrics reveal him to be only average in that department

while Mookie is well established as one of the elite outfielders in the game.

Machado has two Gold Glove awards, but he has never hit .300 in his six years as a major

leaguer, and he does not hustle on every play. In addition, he’s picked up a reputation as a

sometimes dirty player.

If those guys can break the $300 million barrier one shudders to think what kind of

money Betts, or Mike Trout who also comes up for free agency in 2020, will command.

$350 million? $400 Million? Infinity?

The Red Sox have tried to engage Mookie in talks to head off his free agency, but his

representatives prefer to test the market. There is, of course, a certain amount of risk to

that strategy. What if Betts should be seriously injured sometime in the next two years?

What if, for whatever reason, his numbers should suffer a sharp decline? The stakes are

high on both sides of the ledger. From the Red Sox (or any team’s) point of view, long-

term contracts are a recipe for disaster.

Exhibit A is Albert Pujols. In eleven years with the St. Louis Cardinals, Pujols had

established himself as one of the greatest hitters of all time. He had a lifetime batting

average of .328 and hit an average of 40 home runs a year. So the Los Angeles Angels

wooed him away with a ten year contract worth $240 million. Pujols has never even

flirted with a .300 batting average since then. In seven years with the Angels he’s hit for

an average of just .260 with only 29 home runs a year. His decline has become steeper

each year; in 2018 he hit only .241 with 19 homers. He’s become injury prone and he

runs in slow motion. Clearly, the end is near for him as a player. But his fat-cat contract

has three more seasons to go.

After the 2007 season Alex Rodriguez signed a ten year contract with the New York

Yankees worth $275 million, but it wasn’t long before he became a public relations

nightmare for the Yankees and for himself over his involvement in the steroids scandal.

He was suspended for the entire 2014 season. Age caught up with him too, and the

Yankees released him in August, 2016, with more than a year to go on his very expensive


Committing long-term big dollars to a player is a risky business; it’s like jumping from a

plane with an untested parachute. Remember Pablo Sandoval? The folks in the Red Sox

accounting office certainly do; they’re still cutting checks to him at the rate of $18

million annually until the end of this year. Then he’ll get a $5 million buyoutfor next


Ten year contracts are crazy, there can be no doubt. But what if it’s Mookie Betts?

Maybe, just maybe, he’d be the exception to prove the rule. After all, if Babe Ruth had

been able to declare free agency after six years in the big leagues and signed a ten year

contract, he’d have been well worth the price. In 1929, which would have been the last

year of his deal, he led the majors in home runs with 46, batted .345 and knocked in 154

runs. If Ted Williams had done the same, the final season of his ten year deal would have

been 1957, when he only managed a batting average of .388! So it can be done, or at least

it could have once upon a time.

Sam Kennedy, Dave Dombrowsky, and their minions have serious decisions to make

even before confronting the issue of Mookie’s free agency. What will they recommend

that John Henry, Tom Werner, and their partners spend next year on J.D. Martinez? He

has an opt out on his current deal that pays him $23.7 million a year. That’s a whole

bunch of money, but it’s a bargain for what he produced last year - .330 batting average,

43 home runs, and 130 runs batted in. If he does that again this season, he might

command $35 million a year on the open market, which would be a record for an

individual year for a non-pitcher. What about Chris Sale, who is up for free agency after

this season? When he’s healthy, he’s as good as any pitcher on the planet. Let’s not forget

Rick Porcello, also in his free agency year; he might not be quite a Chris Sale, but he’s

dependabe and very durable. To resign just Martinez, Sale, and Porcello after this year

could cost $100 million per year. And then there is Mookie, to say nothing of Xander


The Red Sox brass cannot and will not sign them all. They already have the highest

payroll in baseball, and, even with limited resignings, it’s going to get higher, much

higher. This year’s edition looks much like last year, which is fine by me, but down the

road it’s going to change.

Here’s what I recommend we all do in the 2019 season: learn, or relearn the lyrics to that

old song, “Enjoy Yourself, It’s Later Than You Think.”