Tomase: Ranking the Red Sox free agents -- their first choice is our last

John Tomase
February 21, 2019 - 8:40 am

Here's a tale as old as No, No, Nanette: you can't pay everyone.

Even baseball's highest payroll isn't limitless, and Red Sox owner John Henry made it clear on Monday that he won't run the Red Sox as a loss leader.

"We have free agency in baseball," Henry said. "We have a lot of young players who will mature at the same time, mature for free agency. We won't be able to keep all of them."

That leads to an obvious question: How should they prioritize the six star-caliber players whose contracts expire either this year or next?

Come fall, they'll need to make decisions on ace Chris Sale, slugging DH J.D. Martinez, right-hander Rick Porcello, and shortstop Xander Bogaerts. Next year brings MVP Mookie Betts and Gold Glove center fielder Jackie Bradley Jr.

A serious reckoning looms. Here's how we'd order the plan of attack.

1. Mookie Betts

Manny Machado's 10-year, $300 million contract from the Padres probably serves as the floor, but Betts is worth every penny. The defending American League MVP is a classic five-tool superstar who's not eligible for free agency until after next season, which gives the Red Sox some time to negotiate an extension. He'll have just turned 28 when he hits the market, and if you're going to bet big, an outfielder with perennial 30-30 potential is the place to do it. With all due respect to everyone else on this list, if the Red Sox can only keep one player, the choice is easy. They should just prepare to do so in free agency, because Betts seems likely to test the market.

2. J.D. Martinez

Though technically not a free agent unless he opts out this fall, it's a safe bet that Martinez will seek greener pastures, so to speak, if he produces a sophomore effort anywhere near his monstrous .330-43-130 Red Sox debut. Only two other players in franchise history have reached those markers in the same season, and both are in the Hall of Fame -- Ted Williams and Jimmie Foxx. The Red Sox learned in 2017 what life can be like without an old-fashioned slugger anchoring their lineup. David Ortiz filled that role from 2003-16, and there's no reason the 31-year-old Martinez can't carry the torch well into the next decade. He always felt underpaid at five years and $110 million, and he'll likely command something in the $150 million range on the open market. The Red Sox should pay it and lock down their two best hitters for the next six years.

3. Rick Porcello

Few commodities are more valuable than certainty, and Porcello provides it. The right-hander has made between 31 and 33 starts in eight of his 10 big league seasons as a modern-day Derek Lowe. He's probably not going to win another Cy Young Award, but 30 starts and 200 innings of league-average ERA have their place in any rotation. The sinker-balling Lowe went 85-70 with a 3.82 ERA in his first six seasons after leaving Boston, with between 12 and 16 wins each year. It's easy to envision Porcello providing similar returns, and unlike ace Chris Sale, he's not going to cost $30 million per season. He's more likely to remain at the $20 million level that seemed like an overpay but turned out to be money well spent when GM Ben Cherington extended him in 2016.

4. Jackie Bradley Jr.

Why Bradley instead of Xander Bogaerts, who's clearly a better offensive player at an even more important position? Two reasons -- defense and price. There's one elite skill between the two of them, and it's Bradley's glove. He's probably already the best defensive center fielder in Red Sox history, and if his second-half offensive surge in 2018 is to be believed, perhaps he's ready to become a more complete player. Even if he isn't, his inconsistent performance should weaken his bargaining position, since his average and OPS have declined each of the last three seasons. Even with Scott Boras as an agent, he's more likely to land in a range the Red Sox can afford.

5. Xander Bogaerts

When Henry wistfully notes the Red Sox won't be able to keep everyone, he's probably picturing Bogaerts, who becomes eligible for free agency in the fall. A two-time World Series champion, Bogaerts nonetheless hasn't reached the heights predicted for him when he started the 2013 clincher at age 21. Young shortstops like Cleveland's Francisco Lindor, Houston's Carlos Correa, and Colorado's Trevor Story have surpassed him, and his glove has regressed enough over the last two years to question the wisdom of committing to him long-term at the position. He did just compile his best offensive season, however, and if he builds on last year's .288-23-103-.883, he'll almost certainly price himself out of Boston. It's too bad, because he plays the game right, is homegrown, and carries himself with poise, but there simply isn't money for everyone.

6. Chris Sale

First on the team's list and last on ours. Sorry, but the combination of a funky delivery, last season's alarming shoulder injury, and a history of second-half fades simply makes Sale too much of a risk for the eight years and $200-plus million it will take to retain him. If you could guarantee Sale's health for even the next three years, he might earn enough to offset the inevitable late-contract fade. But do the Red Sox really want more than $60 million annually tied up in one pitcher with a bad elbow (David Price) and another with a bad shoulder? The risk is overwhelming, which makes it mildly surprising that the Red Sox have prioritized Sale among this year's free agents. He may be everything the Red Sox could want in an ace from a performance, leadership, and demeanor standpoint, but those attributes mean nothing if he's injured. It will hurt like hell in the short term, but best to let him go and explore Plan B.