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It’s almost payday for some of the Red Sox’ top young players

From left, Jackie Bradley Jr., Xander Bogaerts, Mookie Betts, and Andrew Benintendi.Patrick Semansky/AP

There comes a time for every franchise when the bill comes due. When you have good, young players they eventually become good, high-priced players. The advantages you enjoyed while they were making little money and producing are suddenly gone.

The Red Sox still have time with Andrew Benintendi and Rafael Devers, but the bill is about to come due on Chris Sale, Mookie Betts, Xander Bogaerts, and Jackie Bradley Jr., among others.

The luxury-tax threshold is $197 million, and there is a 20 percent tax on that. Two surcharges follow, at $217 million and $237 million. The Red Sox’ payroll is already at around $234 million, $17 million more than the first tax surcharge. They are charged a 12 percent tax on the overage. Should they exceed $237 million, an additional 45 percent would be charged. Given the revenues the Red Sox enjoy, they could certainly push it and pay the tax, but the penalty also includes losing 10 slots in the draft order if they go over that second threshold.

The first threshold will be raised to $206 million in 2019 so that should help the Red Sox’ ability to retain some of their stars. Suffice it to say, not everyone is going to get re-signed. The hope is that you can replenish your core every five or so years, but in Boston’s case you don’t see many players in their farm system who you can project being in the position to replace Bogaerts, Betts, or Bradley when they become free agents.


Red Sox president of baseball operations Dave Dombrowski said he projects payroll five years down the road, and normally the projections are pretty accurate, though he warns “there are so many factors involved that could change.” The projections could go haywire if there are injuries and a need for replacement players. There’s dead money, as is the case now with Pablo Sandoval and Hanley Ramirez, that has to be accounted for.


Here is what’s facing Dombrowski and the Red Sox ownership over the next couple of years:

AFTER 2018

Craig Kimbrel — He is first and foremost on Dombrowski’s plate, and Red Sox ownership will have to think about whether to re-sign the closer. Kimbrel can certainly make a legitimate case for an Aroldis Chapman deal of five years, $86 million. Will the Red Sox go there for a closer? It’s tough enough for the Red Sox to commit big dollars and years to starters, let alone closers. If you choose to part ways, who would replace him? The Red Sox could give the job to Joe Kelly, but there’s really no standout candidate internally to replace Kimbrel. The Red Sox would have to think about a cheaper possibility such as Baltimore lefthander Zach Britton, who would likely not demand the salary Kimbrel will demand.

Joe Kelly — Boston’s setup man will also be a free agent. He will be in demand because of his stuff and velocity. It’s hard to envision the Red Sox being able to re-sign both Kimbrel and Kelly, but that’s what they’re faced with. Kelly could get a three-year, $27 million deal somewhere.

Joe Kelly had a 3.47 ERA through 38 appearances this season.Jim Davis/Globe Staff

Drew Pomeranz — The first half of 2018 has been a wasted year for the tall lefthander, but if he recovers and has a solid second half, the Red Sox would have to think about re-signing an under-30 starter (he turns 30 on Nov. 22) who won 17 games just a year ago. If he has a good second half, don’t be surprised if he gets an Alex Cobb-like four-year, $52 million deal.


David Price — He has an opt-out after this season, but don’t expect him to exercise it unless he’s so miserable with the Red Sox that he would leave millions on the table. We expect that the Red Sox will be sending him checks for the next four years.

AFTER 2019

Chris Sale — Buckle up on this one. The Red Sox need to get to this long before he becomes a free agent. The team does hold a 2019 option for $13.5 million. If Price got seven years, $217 million, won’t Sale be demanding something in the same range? Sale will likely be a $30 million-per-year pitcher, which means he’ll go from $13.5 million after 2019 to $30 million on what could be a five- to seven-year deal. Quite a leap. There’ll be plenty of interest. The question is, will Sale get seven years or will he have to settle for five for an annual average of $30 million? Then you have to ask, how many $30 million pitchers can one staff have?

Rick Porcello — Yes, his four-year, $82.5 million deal will be up. He’ll be 31 when he seeks free agency. He’s on his way to having a very good 2018. For some reason, Porcello has had good seasons every other year. It seems logical that Porcello will hold his value in the $20 million-$25 million-per-year range even in his early 30s. Again, how many of these high-priced guys are the Red Sox willing to pay?


J.D. Martinez — He’s scheduled to earn $23.75 million in 2020, so if Martinez is putting up big numbers would he use his $2.5 million buyout of the remaining three years or would he try to renegotiate a bigger deal with the hope of getting a new contract that averages about $30 million a year? This is something to watch because Martinez’s agent, Scott Boras, has always felt that his client got less than what was expected.

Through 84 games, J.D. Martinez had 27 home runs.Matthew J. Lee/Globe staff/Globe Staff

Xander Bogaerts — The shortstop will enter free agency relatively young at 27, and if his game is still very good, he would receive lots of interest. Is he a player the Red Sox want to attempt to sign before free agency comes up? Boras has recently signed more of those types of deals to head off free agency. Bogaerts could land a five- to seven-year deal in the $20 million-a-year range.

Mitch Moreland — He has a two-year deal that ends after 2019. The first baseman is a good player, plus-defender, and a solid teammate. He’s considered a complementary player and won’t break the bank should he still be an asset and the Red Sox want him to return.

AFTER 2020

Mookie Betts — He has resisted the temptation of signing a long-term deal pre-free agency, and you can understand why. Betts and the Angels’ Mike Trout will hit free agency at the same time, and you can bet both organizations will try hard to head that off. Trout will likely become the highest-paid player in the game, but if Betts continues on his present path, are we talking $30 million, $35 million, maybe even $40 million? A seven-year, $260 million deal?


Jackie Bradley Jr. — The center fielder will be the least expensive of his free agent teammates, and one supposes the Red Sox have a couple of years to determine whether he’s worth the outlay over a multiyear deal. Bradley is still a great defender and so-so offensive player, so the Red Sox would likely take a pass.

Apropos of nothing

Nolan Arenado (right) is in his sixth season in MLB.Justin Edmonds/Getty Images

1. You can’t blame Nolan Arenado or Mike Trout for wanting to win. Arenado has played in only one sudden-death playoff game in his career in Colorado, and Trout has appeared in just one playoff series, in 2014. It was sad that Ernie Banks, one of the greatest players this game has known, never played in a postseason game during his long, illustrious career. Arenado’s frustration came out during the week when he discussed the Rockies’ plight. The Gold Glove third baseman came into the season feeling the Rockies were going to accomplish something special, only to be disappointed with underperforming teammates. The same holds true for Trout. All great players want to show their talents when it counts most.

2. What managers are on the hot seat during the second half of the year? It may be that nobody is. Buck Showalter’s Orioles have been a nightmare. Mike Scioscia’s Angels have suffered many injuries, but they’ve been awful. On the flip side, the top two managers in the league have been Tampa Bay’s Kevin Cash and Oakland’s Bob Melvin, a pair of former Red Sox backup catchers. In the NL, Atlanta’s Brian Snitker and the Phillies’ Gabe Kapler are heading toward serious Manager of the Year consideration.

3. It’s obvious that commissioner Ron Manfred wants the DH in the National League. I’m all for tradition, but it’s time for the resistant NL owners to give in. While Jon Lester has found his batting stroke so many years into his career, and while Rick Porcello helped the Red Sox beat Max Scherzer last Monday, watching the pitcher hit is a waste of time.

4. As evaluators for contenders start heating up their coverage of available players to acquire, one thing they keep in mind is this: Can that player go from a no-pressure, non-winning situation to the heat of a pennant race? This is where scouts and GMs really have to assess the players they’re pursuing. That’s why so many teams want Adrian Beltre. That’s why as good as Kyle Barraclough has been in Miami and Raisel Iglesias has been in Cincinnati, there’s that question — would those two relievers be as effective working in the stressful innings of a pennant race? It’s not an easy thing to measure. You can go by the numbers and they usually don’t lie, but they don’t tell you whether a guy can pitch a ninth inning with a one-run lead at Yankee Stadium.

Kyle Barraclough was an All-Star in 2015, 2016, and 2017.Mark Brown/Getty Images

5. Who was the last pitcher the Red Sox developed? Clay Buchholz? My goodness, it’s been a dark hole for this organization for a long time and the result has been having to sign pitchers to enormous contracts.

6. There have been a few mistakes made by the Red Sox that have cost the organization millions. The Hanley Ramirez, Pablo Sandoval, and Rusney Castillo contracts were awful. The acquisition of Allen Craig in the John Lackey deal was also horrible. But the biggest mistake of all? Not re-signing Lester. The Red Sox could have had him for about $120 million over seven years. Lester is now in the fourth year of a six-year, $155 million deal with the Chicago Cubs, and he’s 11-2 with a 2.25 ERA. He earns $27.5 million this year and next, and $20 million in 2020. There’s a $25 million option in 2021. Still a bargain. Yet, after all the mistakes and lack of pitcher development, the Red Sox have won more games than any team in baseball.

7. The Braves, Indians, Phillies, Dodgers, and Brewers are mentioned a lot with Manny Machado. The Cardinals are another team that should be in the hunt for the Orioles shortstop as they need something to energize that team. But one team to watch is the Nationals. As they start to fade in the National League East, they too need a fix. What they would do with shortstop Trae Turner and/or third baseman Anthony Rendon is up to GM Mike Rizzo, but the Orioles probably would love to get Turner as part of a return package. The Nationals have the players that would entice the Orioles, including outfielder Victor Robles, 21, currently on the Triple A disabled list.

8. Topps will for the first time feature a scientist — Dr. Lawrence Rocks — on Paul DeJong’s Future Stars card to commemorate their baseball temperature study in the offseason.

Updates on nine

1. Francisco Mejia, C, Indians — He is the player the Orioles would have to get in any Manny Machado deal. The switch-hitting Mejia, 22, is having a strong season at Triple A Columbus, hitting .285 with seven homers and 41 RBIs. The Indians would balk at parting with such a good prospect for a rental, but the sons of Terry Francona are happy with their catching tandem of Yan Gomes and Roberto Perez.

2. Bryce Harper, OF, Nationals — ESPN analyst Eduardo Perez brought up a good point: If the Nationals feel they’ve fallen out of the race by the trade deadline, would they consider trading Harper and then reacquiring him in the offseason? This would be akin to the Aroldis Chapman deal in which Yankees GM Brian Cashman dealt him to the Cubs at the 2016 trading deadline, got back Gleyber Torres in the deal, then re-signed Chapman in the offseason.

3. Bobby Dalbec, 3B, Red Sox — Earlier this season Dalbec was going so bad that opposing scouts were of the opinion that he should go back to being a pitcher. He’s come a long way since, and he is now showing positive signs albeit at advanced Single A Salem as a 23-year-old. The third baseman leads the league in slugging (.517), home runs (17), doubles (24), and RBIs (64).

4. Travis Shaw, 3B, Brewers — He has never been able to play his best position — first base — in Milwaukee. He’s only played 4⅔ innings at first since joining the Brewers last season. Shaw is now taking ground balls at second base, and at least he’s on his better side of the diamond. Shaw, who was acquired from the Red Sox in the Tyler Thornburg trade, has been dealing with a sore wrist that has hampered his swing.

5. Zach Britton, LHP, Orioles — According to a major league source, there are “a couple” of scenarios where Britton could be traded in tandem with Machado or another Orioles reliever. Britton has been working toward knocking the rust off and seems to be making some progress. The Orioles are trying to get maximum return for him, but the fact he hasn’t pitched much the last two years doesn’t help.

6. Josh Donaldson, 3B, Blue Jays — The best the Blue Jays can hope for regarding the oft-injured infielder is that he’s an August trade candidate. It would appear Donaldson would clear waivers and the Jays would be able to move him to a contender. But counting on a healthy Donaldson by the end of August is also an iffy proposition.

7. Blake Treinen, RHP, Athletics — The A’s are putting out the word that their closer (22 saves) is not available, which some teams are seeing as a sign that he is — but that it will cost a lot to get him. The A’s have certainly overachieved, but entering the weekend they still trailed the Mariners by 7½ games for the second wild-card spot in the AL.

8. Wilson Ramos, C, Rays — The Nationals recently dispatched special assistant Dan Jennings to watch Ramos, their former catcher who was having his best season in Washington two years ago before he tore up his knee. Ramos is having another fine season (.291/12/45) and it’s not so farfetched he could return to the Nationals.

9. Jose Abreu, 1B, White Sox — There’s been a strong flirtation by the Astros with Abreu. While they’re monitoring the bullpen market, they could easily switch gears and pull this off. If they do, according to one scout, “Print the World Series tickets.”

Extra innings

From the Bill Chuck files — “Juan Pierre, whose last season was 2013, stole home twice in 2010, just like Javy Baez this season. Also, Pierre had 2,217 career hits and never made the All-Star team, which puts him just ahead of Nick Markakis, who has 2,160 hits and has never made the All-Star team (but that’s about to change).” . . . Also, “Through July 4, J.D. Martinez had 35 multihit games; he had 36 all last season. His high is 45 in 2015.” . . . Happy birthday, Matt Mantei (45), Glenn Hoffman (60). and Chuck Goggin (73).

Nick Cafardo can be reached at Follow him on Twitter @nickcafardo. Material from interviews, wire services, other beat writers, and league and team sources was used in this report.