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BOSTON, MA. - JULY 31: David Dombrowski, President of Baseball Operations for the Boston Red Sox, speaks about the trade deadline before the MLB game against the Tampa Bay Rays at Fenway Park on July 31, 2019 in Boston, Massachusetts.  (Staff Photo By Matt Stone/MediaNews Group/Boston Herald)
BOSTON, MA. – JULY 31: David Dombrowski, President of Baseball Operations for the Boston Red Sox, speaks about the trade deadline before the MLB game against the Tampa Bay Rays at Fenway Park on July 31, 2019 in Boston, Massachusetts. (Staff Photo By Matt Stone/MediaNews Group/Boston Herald)
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The season isn’t over, but it’s fading fast while the future has become the priority for a Red Sox organization about to enter a critical fork in the road.

Do they stick with the current leadership in the front office, where John Henry is spending at a record rate but the Red Sox are having a historically disappointing season?

Or is it time for new voices to be heard as the Red Sox, already locked into exuberant contracts with little room for flexibility, begin to think creatively about staying competitive while trying to rebuild a depleted farm system?

President of baseball operations Dave Dombrowski has had an eventful tenure since joining the Red Sox in August 2015. The Sox have won the American League East three years a row, but at a steep price of record-high spending, both in cash in prospects.

As the Sox consider whether or not Dombrowski is the right man to lead them into the next chapter, here’s a look back at his best and worst moves in his current position:

Dombrowski’s best moves:

FORT MYERS, FL – FEBRUARY 14: Alex Cora #20 of the Boston Red Sox, left, talks with Red Sox president of baseball operations Dave Dombrowski during a spring training workout in Fort Myers, Florida on February 14, 2019. (Staff Photo By Christopher Evans/MediaNews Group/Boston Herald)

1. Hiring Alex Cora
This one wasn’t rocket science. Somebody was going to hire Cora, who was so well-liked and well-regarded throughout the industry that this decision was about as easy as drafting Bryce Harper first overall in 2010. Clearly, Cora made some mistakes in 2019. But there’s little doubt he’s still the man for the job and should have a long successful career in the game. And he and Dombrowski appear to have a respectful working relationship.

2. Extending Xander Bogaerts
Just imagine the troubling future of the Red Sox had Bogaerts not been signed to a six-year extension for just $20 million per year prior to this season. He entered Thursday as the fourth-most valuable player in baseball, per FanGraphs WAR (5.4), while having a career year offensively and defensively as the Red Sox’ ironman shortstop. On an open market, he could’ve pushed $25 to $30 million per season. But Dombrowski doesn’t get all the credit for this one; Bogaerts told agent Scott Boras he wanted to sign rather than start the year without a contract and was willing to take less money to do it. Call him the Tom Brady of the Red Sox.

3. Signing J.D. Martinez
Dombrowski deserves credit for reading the market correctly at a difficult time when baseball was making the turn away from veterans and toward younger, cheaper players. Five years and $110 million for Martinez is already a win for the Sox, who leaned on his artistic approach to hitting on their way to a title in 2018.

4. Trading for Nathan Eovaldi
The Red Sox will never regret this trade. Jalen Beeks has pitched better than expected since joining the Rays, but Eovaldi was everything the Sox needed in the 2018 postseason. Forget about his relief performance against the Dodgers in Game 3 of the World Series — the Sox still lost that game. His larger contribution: twice the Red Sox hit the road in a 1-1 series and sent Eovaldi to the mound in a pivotal Game 3, and twice Eovaldi tossed a gem, holding the potent Yankees and Astros lineups to three total runs in 11 innings.

5. Trading for Chris Sale
The most important piece of information to remember about this trade is that the White Sox wanted Rafael Devers and the Red Sox said no. Devers wasn’t signed by Dombrowski – the credit belongs to Cherington – but that Dombrowski refused to let go of Devers has kept the Red Sox future looking bright. Yoan Moncada is having a nice year but has still produced just 6.5 WAR in three seasons in Chicago while Michael Kopech needed Tommy John surgery. Sale, on a team-friendly contract, has been worth 14.5 WAR.

Rapid fire:

6. Trading for Craig Kimbrel
Kimbrel had his problems but remained a dominant closer while none of the players the Red Sox gave up have done much for the Padres.

7. Trading for Eduardo Nunez
A midseason deal in which Dombrowski gave up nobody memorable, Nunez gave life to a 2017 team that badly needed it.

8. Trading for Steve Pearce
In need of a lefty-masher after Hanley Ramirez was released, the Sox got Pearce for nothing and watched him become World Series MVP.

9. Signing Ryan Brasier
Signed on a minor league deal before 2018, Brasier became a key weapon in the bullpen and recorded crucial outs in the postseason, though he’s back in the minors after struggling this year.

Dombrowski’s worst moves:

1. Keeping John Farrell two seasons too long
As great as Cora has been for this franchise, it’s hard not to wonder what might’ve become of the 2016 or 2017 Red Sox teams, both full of talent, had Torey Lovullo been the manager. Lovullo was the clear heir to Farrell in the Sox’ dugout and was widely seen as an exciting managerial prospect. Former Sox general manager Mike Hazen turned down Cora to hire Lovullo as the Diamondbacks manager before the 2017 season. But Dombrowski insisted on keeping Farrell around in 2016, ignored the obvious signs that it wasn’t working during the year, forgave him for a horrible postseason and brought him back for another rocky ride in 2017.

FILE – In this Dec. 4, 2015, file photo, Boston Red Sox pitcher David Price, left, smiles at president of baseball operations Dave Dombrowski during a news conference announcing his signing by the team at Fenway Park in Boston. Spring training is a time for optimism, when players bask under the warm sun of Florida and Arizona while fans dream about their team playing under the bright lights of October. (AP Photo/Winslow Townson, File)

2. Signing David Price
Including this season, Price has made $121 million in a Red Sox uniform with an ERA close to 4.00 while missing half of the 2017 season. He’s on the injured list again. And while he gets a lot of credit for the 2018 postseason, Price was forgettably horrible in his first two starts against the Yankees in Game 2 of the ALDS and the Astros in Game 2 of the ALCS. He was similarly awful in Game 2 of the ALDS in 2016. The Sox still owe the soon-to-be-34-year-old $96 million over the next three years.

3. Not enough pitching in 2019
Halfway through the 2019 season, Henry was already willing to admit that Dombrowski’s strategy, re-signing Eovaldi and Pearce as the only offseason moves, was a failure. “My take is that maybe it isn’t the best thing in the world to bring back the same team in its entirety every time,” Henry told WEEI in June. There was no depth in the rotation. There was no depth in the bullpen. And Dombrowski did little to help midseason, acquiring only the struggling Andrew Cashner while Cora’s group sank further in the standings. Henry’s $240-million team now looks like it’ll miss the postseason.

4. Trading Travis Shaw to the Brewers (and leaving third base to Pablo Sandoval) for Tyler Thornburg
From 2017 to 2018, Shaw hit 63 homers and was worth 7 WAR while playing a solid third base for the Brewers. In that same time, the Red Sox ranked 29th in MLB with 0.8 WAR at third base. Dombrowski put all his eggs in the basket of Sandoval, who was out of shape and finally let go after 32 disastrous games in 2017. Thornburg arrived with red flags (elbow problems) and departed with more (thoracic outlet syndrome). Worse, the Sox made him their highest-paid reliever entering 2019 and planned on him as part of the back-end of their bullpen.

5. Drafting Jay Groome 12th overall in 2016
This one is tricky, because Groome hasn’t pitched in two years due to Tommy John surgery and it remains to be seen if he’ll be an impact big league pitcher. But at No. 12 overall, the Sox had a chance to find a stud. They used that opportunity to gamble on someone with several off-the-field issues and questions about his character that led to Vanderbilt University withdrawing their interest from the high school standout. Time will tell, but this decision was dubious from the start.

Rapid fire:

6. Re-signing Eovaldi
Buying high on his talent and ignoring his injury history, the Sox linked him to a $68-million deal over four years and had no backup plan when he needed elbow surgery four starts into the season.

7. Re-signing Nunez
See the trend? Another player with a serious injury history that was ignored, Nunez was re-signed to a two-year deal after 2017 and never looked the same while trying to play on one knee for much of 2018.

BOSTON MA. – APRIL 28: Dustin Pedroia sits in the dugout during the 1st inning of the game against the Tampa Bay Rays at Fenway Park on April 28, 2019 in Boston, MA. (Staff Photo By Nancy Lane/MediaNews Group/Boston Herald)

8. No back-up plan for Dustin Pedroia
All-in on the 35-year-old second baseman with a guinea-pig knee surgery, the Red Sox acquired no other second basemen and counted on Pedroia and the aging/injured Nunez as the second basemen this season.

9. Re-signing Pearce
Instead of using this money to find a bargain in the relief market, the Sox offered $6.25 million to the 36-year-old first baseman two weeks after the World Series. He’s hit one home run since.

10. Not attempting to re-sign Rich Hill
The local boy was dominant in a magical finish to the 2015 season, but the Sox chose not to pursue him in the off-season because Dombrowski said they viewed him as a reliever and had no need for a lefty in the bullpen. Hill signed for just $6 million and went 12-5 with a 2.12 ERA for the A’s and Dodgers in 2016.

11. Wasting Blake Swihart
Though it seemed clear to most talent evaluators that Swihart wasn’t ever going to be an elite catcher, the Sox roped him back and forth for years, never letting him settle in at one position nor trying him at third base when they had no other options in 2017.

12. Not offering David Ortiz a contract for 2017
Ortiz said he was retiring after 2016 and the Sox took his word for it, never bothering to draw up a contract and at least give the franchise icon something to think about. A near-MVP season in 2016 ended in disastrous form because Dombrowski never traded for a starter until after the season.

Summary:

Four of Dombrowski’s five best moves involved expensive acquisitions with Henry’s money or Cherington’s prospects.

If the Red Sox are ready to stop spending their way out of trouble and start looking toward building another consistent winner in the future, perhaps there are more creative leaders for the job.

But if Henry wants to go all-in on 2020 to see out Dombrowski’s contract before Mookie Betts hits free agency, he could get another year to prove himself in Boston.