MLB: Boston Red Sox at Tampa Bay Rays

Red Sox manager Alex Cora, left, and president of baseball operations Dave Dombrowski share a laugh last month. Dombrowski was let go by the team Sunday night after a 10-5 loss to the N.Y. Yankees.

As the Red Sox begin to fall further into obscurity on their way toward missing the playoffs one year after winning the World Series, all members of the organization must be prepared for uncomfortable conversations.

Dave Dombrowski already is participating.

With one year left on his contract, the 63-year-old president of baseball operations hasn’t ignored the public chatter surrounding his job security.

“I know it’s a topic of conversation,” Dombrowski said during an interview on the WEEI/NESN Jimmy Fund Radio Telethon on Wednesday. “You’d have to be blind (to miss it). It is what it is. I love being here, have a great relationship with ownership. We have a good front office, we’ve had a good team, we’ve won three divisional titles and a world championship. We’re not out of the postseason at this time. You live with it.”

Dombrowski, who previously worked in Chicago (his hometown), Montreal, Florida and Detroit, is on the record saying Boston has lived up to its reputation of being a tough sports town.

“I think there’s a little bit more (scrutiny) here,” he said Wednesday. “Actually when I do say that, I go around the city and I know not everybody supports any individual on whatever they do, but the fans here are fantastic to me wherever I go. Every so often I’ll hear, ‘Go get a reliever,’ or, ‘Go get a starter.’ That’s there everywhere. That’s just how it is. The fans are very good, and hopefully I’m here for a long time.”

Soon enough, Dombrowski should know his fate.

Red Sox principal owner John Henry has been talking about extending Dombrowski’s contract since hoisting the World Series trophy last October.

Just before the parade, Henry was asked about extending Chris Sale’s contract and stopped mid-answer to add Dombrowski, too, would soon require a new deal.

A few months later, during a press conference in spring training, Henry said this about Dombrowski’s contract: “This day and age, it probably doesn’t make sense for your general manager to go into his final year without a contract, so that would mean something should happen this year.”

He’s right about that. One way or the other, something should happen before this conversation becomes a cloud lingering over the team.

A lame-duck leader in the front office is the last thing the Sox need as they enter 2020 with too many other things to worry about, like coming back from a disappointing season and Mookie Betts’ pending free agency.

“I have a contract for next year,” Dombrowski said while on the air Wednesday. “Am I confident? I go about doing my business as I would on an everyday basis and hopeful I will be here. Unless somebody tells me I’m not, you operate that way. And I do know when people write an article (about my job security). The one thing I’ll say, there’s no inside information. Our organization, the people that make that kind of decision are John Henry, Tom Werner and Mike Gordon, and I know they’re not getting information from them.”

Dombrowski’s previous point about Boston being a tough town is well-taken. He’s been in charge for three off-seasons that resulted in three straight division titles and a World Series. This year will likely be the first in which he’s built a Red Sox roster that fails to make the playoffs.

But the conversation about Dombrowski’s future shouldn’t be focused on his perceived failures, but instead on whether his style of leadership is the right one for the Red Sox moving forward.

He’s been great at dishing out prospects for proven star players and has had success doing so. When the prospects run out, however, his job changes.

When the Red Sox enter 2020 with limited financial flexibility, his job changes again.

Asked about Betts, Dombrowski said, “You can be sure from an ownership perspective, from a club persepctive, we’ll do everything we can to keep him.”

Asked about Chris Sale’s five-year, $145-million contract extension, he said, “We thought we got a bargain at that point at five years with somebody going into their age 30 year... We thought it was the right move. And I think over time it will be the right move, just this year hasn’t been quite the way we had anticipated.”

But in 2020, no longer will the Sox need a leader who can identify the right stars to acquire. Instead, they need to develop their own, all while finding more creative ways to upgrade the big league roster.

And until Henry decides to extend Dombrowski or let him go, the conversation will continue.

At least we know Dombrowski is willing to participate.