As Red Sox CEO Sam Kennedy and manager Alex Cora sat down for Monday’s year-end press conference, Kennedy started by acknowledging how an already difficult time took an unimaginable turn for the worse over the weekend. The death of franchise icon Tim Wakefield was a tragedy, one that’s being felt by everyone associated with the Red Sox.

“It indeed was perhaps the saddest day in the 123-year history of the Boston Red Sox organization,” Kennedy said, before going on to offer his condolences to Wakefield’s family, friends, former teammates and everyone else affected by his passing. “Losing an icon like Tim Wakefield is an incredibly difficult thing and we feel your pain.”

Wakefield’s loss and legacy loom large over a franchise that has lately strayed from the ideals he embodied. Nobody took more pride in being a member of the Boston Red Sox, and now coming off consecutive last-place finishes the first order of business this offseason will be finding someone who can help get the Red Sox back to being the Red Sox.

The search for a new head of baseball operations is well underway, and Kennedy said during Monday’s hour-long presser that this year’s process will be much more drawn out than the previous one in 2019 that led to Chaim Bloom’s hiring.

“We plan to take our time, we plan to be very deliberate, we’re going to have internal candidates, we’re going to have external candidates, we’re going to have a consistent robust process that hopefully leads us to the right person, or people,” Kennedy said. “We’ve been underway since announcing the change and we don’t have any set deadline or timeframe, we’re going to go through this process this offseason and we’ll have an announcement when it’s appropriate.”

Though Kennedy wouldn’t name any specific candidates or how many the club had identified, he said the Red Sox have sought permission to interview certain people and expect to begin conducting formal interviews by the end of the week or by early next week.

While keeping an open mind as far as what kind of person they’d like to hire, Kennedy said the most important thing is to find someone passionate about winning in Boston and reiterated the club’s long-stated goal of building towards sustainable success at the major league level.

Kennedy said current front office members will take the lead on running baseball operations until a hire is made, and that decisions on the club’s existing coaching staff will be made in the coming days.

“Those conversations will be ongoing in the days ahead,” Kennedy said. “Primarily staffing decisions will be handled by (Brian O’Halloran) and Eddie (Romero) and Alex (Cora) talking about next year, so early days on that front but those conversations will happen in the days ahead.”

Kennedy also reiterated that Cora will return as manager in 2024, but beyond that he and Cora both said they’ll address a potential long-term contract extension “at the appropriate time.”

With the news of Wakefield’s death so fresh, the Red Sox said they plan to honor the longtime pitcher in the weeks and months to come, but for now nothing specific has been finalized.

That includes the possibility of retiring Wakefield’s No. 49, which has not been worn by any other Red Sox players since his retirement in 2011.

“No talk about anything specific yet but we’ll keep you posted on that,” Kennedy said.

Whether it’s a number retirement, a pregame ceremony, a patch or some combination of things, Kennedy said whatever they do to honor Wakefield will be as inclusive as possible so that fans will have ample opportunity to participate.

Seeing that 2024 will mark the 20th anniversary of the club’s first modern World Series championship team, Kennedy was also asked if former pitcher Curt Schilling will be welcomed back for those festivities, given his recent public behavior and specifically his role in disclosing Wakefield’s cancer without permission.

“I appreciate the question but not something I’ve given one minute of thought to, I’ve just been focused on Wake and his family,” Kennedy said.

While the Red Sox have traditionally ranked among baseball’s top spenders throughout the current ownership group’s tenure, this year’s Opening Day payroll of approximately $225 million only ranked 12th in MLB and 13% above league average, by far the lowest since 2002.

Will the Red Sox flex their financial muscles this coming offseason and raise payroll? Kennedy won’t say.

“We definitely aren’t going to talk about our plans for major league payroll,” he said. “I don’t know why other clubs do that but we do not want to tip our hand to our competitors and talk about major league payroll.”

Kennedy reiterated, as he has frequently in the past, that the front office has always been given the resources it needs to succeed. The problem typically has stemmed from how those resources are allocated, but going forward the club has the financial flexibility it needs to accomplish its goals.

How much the club invests in payroll going forward, or whether or not fans can expect any bold acquisitions, will probably depend in large part on who winds up being hired as the new head of baseball operations.

Last year at the season-end press conference, Alex Cora was asked who he hoped to see the most improvement from over the following offseason, and before the reporter had finished asking the question he responded “Alex Verdugo.”

This year, asked the same question, Cora pointed the finger squarely at himself.

“We’ve got to get better. We’ve got to push these guys to be a lot better,” Cora said. “That’s my challenge this year, me and the coaching staff, we have to be better.”

Cora said he and his coaches met earlier Monday and the main discussion was how can they help their players improve.

Will that include changes on the coaching staff itself?

“I don’t believe so,” Cora said. “I think we just have to be better.”