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NEW YORK — By even a conservative estimate, the Red Sox have added 20 noteworthy prospects to the organization in the 19 months Chaim Bloom has been chief baseball officer.

Via trades, the amateur draft, the Rule 5 draft, and international signings, the Sox have built depth at all levels of the minor leagues.

At the same time, the major league team is ahead of schedule and contending for a playoff spot driven by a better-than-expected pitching staff.

As the July 30 trade deadline approaches, those paths will cross. Which road will Bloom take?

“It’s a tough tightrope to walk. But it’s where we want to be,” he said Sunday before the Red Sox beat the Yankees, 6-5, in 10 innings to sweep a three-game series. “Ideally we have that tightrope that we’re walking every year.”


The Sox are tied for the third-best record in the majors and are playing with a lot of passion. It’s difficult to judge what their specific needs will be at the end of July, but getting more offense from first base, second base, or left field would be a start.

I don’t agree with the idea that a contending team deserves an addition at the trade deadline. Change for the sake of change isn’t a good way to conduct business. But when there is a clear need, standing pat can crush the spirit of a team.

The best general managers are usually juggling three plans at once: now, a few seasons from now, and five years down the road. They have to weigh their decisions accordingly.

Trading the wrong prospect can haunt a team for years. Think the White Sox might want Fernando Tatis Jr. back after dealing him for James Shields in 2016?

What's the next move for Chaim Bloom?
What's the next move for Chaim Bloom?Jim Davis/Globe Staff

“If we want to keep ourselves out of the basement, we have to make sure that no matter how good we are, we’re never just throwing away our future,” Bloom said. “Otherwise you get what you would expect to get if you do that.”


Bloom was hired to pay rapt attention to the five-year plan. His endgame is not returning to the playoffs. It’s winning two or three World Series in a row.

No team has done that since the turn of the century Yankees. But somebody will eventually, and the Red Sox are on the short list of teams with the resources to make it happen.

But Bloom was quick to say he recognizes the opportunity the Sox have created for this season.

“As much as we are in this for the long haul, every chance to make the postseason is important,” he said. “We need to make sure we’re respecting the chance we have this year as well as all the chances we hope and expect to have in years to come.”

Bloom believes the Sox are in a better position to make a trade that would legitimately help the major league without giving away a key piece of the future.

Another factor is the Sox have what for them is a large group of players who would need to be placed on the 40-man roster after the season or be exposed to the Rule 5 Draft.

Prospects such as Jeter Downs, Jarren Duran, Gilberto Jimenez, Brayan Bello, and Josh Winckowski would seem like locks.

Young righthander Thaddeus Ward could be reaching the crossroads of his career.
Young righthander Thaddeus Ward could be reaching the crossroads of his career.John Bazemore

But what of Thaddeus Ward, the talented righthander who just had Tommy John surgery? The Sox will have to decide whether to protect him or risk his becoming their version of Garrett Whitlock.


There are roughly 8-10 other players who could play their way into the 40 and others already on the 40 who could play their way off by the end of July.

That gives Bloom a pool of players he could use to swing a deal. It’s all part of that metaphorical tightrope walk.

“It’s something we’re going to need to look at,” Bloom said. “We always talk about this. We’ve talked about it going back to the offseason, that balance between now and the future and as much as we can trying to do things to help us on both fronts.

“That’s obviously hard to do. It’s not that simple.”

The Sox tried to do both when they traded Andrew Benintendi to the Royals in February. They received five players back — four prospects and left fielder Franchy Cordero. Their hope was Cordero would finally click after being held back by injuries.

Now Cordero is in Triple A after hitting .179 in 34 major league games and Benintendi has been one of Kansas City’s best players.

That trade can’t be fairly judged for another four or five years but for now it’s a bust. Check back in 2025.

Bloom said his nature is never to believe he has enough prospects. But they won’t all play for the Red Sox, that’s for certain.


Starting soon, Bloom, and his staff will have some tough decisions to make — and the major league team will be watching.

Peter Abraham can be reached at peter.abraham@globe.com. Follow him on Twitter @PeteAbe.