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'I love it here, but it's still a business': Mookie Betts' future looms large in Boston

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Lee: Don't bet on Betts staying in Boston (1:27)

Joon Lee doesn't expect Mookie Betts will sign an extension with the Red Sox, because in order for Betts to maximize his value on the market, he has to hit free agency. (1:27)

BOSTON -- When Mookie Betts was growing up, his father, Willie, drilled a lesson into his head.

"You ain't gonna get nothing you don't deserve," he'd tell the young Betts.

So far in his career, Betts has lived out his father's words.

That advice -- to never sell yourself short -- is a major reason Betts' contract situation will be among Boston's most speculated topics in 2020, with no resolution guaranteed until after next season. But the noise will be heard this offseason, too, as Boston faces several franchise-shifting decisions, including whether to trade Betts instead of risking losing him in free agency.

After team president Dave Dombrowski was abruptly fired in the midst of a playoff-less season, the Red Sox elevated senior vice president Raquel Ferreira and assistant general managers Eddie Romero, Brian O'Halloran and Zack Scott to lead the team's front office -- but that's only on an interim basis. It will be up to the new general manager -- once he or she is named -- to figure out how to navigate it all, and to do a job where public criticism always exceeds acclaim, regardless of the team's relative success compared to the rest of the league.

Betts has stated publicly on numerous occasions that he enjoys playing in Boston, and has reiterated that sentiment throughout the course of this season. But he won't sign an extension. Before 2018, Betts took the Red Sox to arbitration, prevailing in his case to the tune of a $10.5 million salary, the largest deal ever for a first-year arbitration-eligible player. The Red Sox and Betts agreed to a one-year, $20 million deal before this season to avoid arbitration, the largest amount given to a second-time arbitration-eligible player. Betts turned down an eight-year, $200 million offer before his first arbitration case two offseasons ago and told reporters in spring training that he doesn't expect anything to happen until he's a free agent.

"It's just been a blessing to be a part of such a great franchise with all of the history and all of the guys who have come through and they still come through," Betts told ESPN in May, before the Red Sox title defense fell apart. "You meet a lot of people. A lot of eyes are on you here, and I've learned if you don't embrace it, it may eat you up.

"You have the opportunity to win every year," Betts said. "Nobody is trying to take a season off. You can't ask for anything more than that. Winning every year, winning is obviously the reason why we play and we've been able to do it every year. It's definitely something I want to be a part of."

Betts says it's his obligation to maximize his value -- and help raise the bar for the next generation of players -- by hitting the free-agent market. Still, Betts and his inner circle of friends from Nashville have maintained for years that the 2018 MVP loves playing for the only franchise he's ever known.

"I'm a confident person in knowing my abilities, but also know, I'm kind of a realist, I know when I suck," Betts said. "I'm confident in my abilities and confident to know what kind of player I am. I've also been educated on the business side of it, getting your value.

"You just have to be able to stand up for yourself. And that's OK," Betts said. "Some people kind of get lost in what everyone else is doing and not pay attention to themselves, and I think I'm one where I pay attention to myself and can set the example for the people coming up. Somebody's gotta do it. I'm more than happy to be the person to do it. I stand on principle."

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Ross: The Sox should pay Betts

David Ross and Tim Kurkjian debate whether the Red Sox should try to keep Mookie Betts or trade him.

The Red Sox now face a decision: Is Betts worth more to them as a trade asset than he is in right field with one year left on his contract and no promises for anything more? The Red Sox need to decide this offseason how they will handle the lack of contract security around their best and most nationally prominent player. Boston will listen to trade offers for Betts, according to front-office sources, but the price will be high: multiple highly regarded prospects, enough to help kick-start a farm system rebuild. Alex Speier of The Boston Globe recently reported that Boston is unlikely to retain both Betts and J.D. Martinez this offseason.

The number of teams that might fit the criteria for the Red Sox, but also make sense as a fit for Betts, is low. Teams would need to be willing to take on what will likely be another record-setting arbitration salary with no guarantee beyond the one year. On top of any salary concerns, teams would need to be in a championship window and willing to part with multiple top-tier prospects, a description that fits few teams at a time when the sport faces a tanking problem.

It's not like the Red Sox are short of money. Boston ranks fifth in attendance in 2019 and Forbes estimates the team is worth $3.2 billion, $2.5 billion more than Henry and his partners paid for it in 2002. Boston, however, is financially motivated to get under the luxury-tax threshold, which is subject to harsher penalties for repeat high spenders -- a threshold they've eclipsed the past two years. The threshold will be $208 million in 2020. The team's least creative solution would be to unload either Betts or Martinez, who own two of the team's biggest salaries.

From the perspective of any potential trade partner, Betts would need to represent a valuable enough upgrade in the outfield to justify the high price required to make a deal. Among the teams who merely fit the description of being in a championship window with prospect capital, without considering on-field or financial fit, are the Dodgers, Braves, Nationals, Cubs, Indians, Cardinals, Angels and Padres. Red Sox president and CEO Sam Kennedy has stated on multiple occasions that he hopes Betts remains in Boston for the rest of his career.

"He's the exact type of player you want to have on your team," Kennedy said in January. "Not just from what he does on the field, but off the field. He's such a great person. We'd love to have him be a Red Sox for his entire career. Certainly understand, you try to put yourself in the other person's shoes. He's going to want to see what the market looks like. Understand that. But we've made it crystal clear to Mookie that we want him to be a part of the Red Sox organization long term."

Much of Boston's championship core, from Betts to Xander Bogaerts to Jackie Bradley Jr. to Andrew Benintendi to Rafael Devers, came up from the farm system. Boston continues working toward the ultimate big-market dream: to build a perennial contender by endlessly developing cheap, affordable young stars, and supplementing that with exceptional financial resources -- a goal much easier to achieve on paper than in practice.

Henry brought in Dombrowski in August 2015 to push the Red Sox roster over the top, and the 2018 World Series was his mission accomplished. At the time, the team boasted one of the most highly regarded farm systems in the league, highlighted by Yoan Moncada, Devers, Benintendi, Anderson Espinoza and Michael Kopech, all considered at one point among the best prospects in the sport.

Two of the five have gone on to become franchise cornerstones in Boston. Espinoza quickly flamed out as an elite prospect upon arrival in San Diego via the Drew Pomeranz trade. As for the two biggest names shipped to Chicago for Chris Sale, Kopech is still highly regarded (though recovering from Tommy John surgery) while Moncada has put together a strong season at the plate for the White Sox, hitting .312/.365/.540. When Dombrowski was hired, Baseball Prospectus ranked the Red Sox farm system as the sixth best in baseball. By 2019, it was last.

Two last-place finishes in 2014 and 2015 did help procure a high draft position. But while Benintendi was taken near the top of the first round in 2015, that spot is no guarantee for a successful prospect. Top pitching prospect Bryan Mata struggled adjusting to Double-A, posting a 5.03 ERA in 11 starts. Some in the Boston front office think 2017 first-round pick Tanner Houck could factor into the major league mix next season, after finishing his season in Triple-A Pawtucket. Fourth-round pick Noah Song, who some teams around baseball viewed as the top pitching prospect in the 2019 draft, has impressed in Single-A Lowell, posting a 1.06 ERA in 17 innings over seven starts, though his future Naval commitments are clouding his future in baseball.

The organization's top prospect, first/third baseman Triston Casas, finished 2019 as a South Atlantic League Season-End All-Star for Single-A Salem, but the organization boasts no top-50 prospect, according to ESPN's Keith Law.

The lack of pitching depth exposed itself in 2019, as Boston struggled to recover from Nathan Eovaldi's early-season surgery, which meant heavy reliance on a taxed bullpen. Dombrowski's replacement will need to figure out a long-term vision for the rotation, which has $237 million tied up through 2022 among three pitchers with injury histories in Sale, Eovaldi and David Price. Sale missed significant chunks of 2018 with shoulder issues, while a visit to James Andrews to check his elbow ended his 2019 season. Eovaldi's health will continue to be under microscopic focus after arm issues derailed his 2019 on top of his two Tommy John surgeries. Price has made 30 starts just twice in four seasons in Boston and Wednesday was shut down for the remainder of the season with a cyst in his wrist.

The Red Sox will have money to spend on the rotation as Rick Porcello's return to Boston looks unlikely, with his $21 million salary coming off the books. Eduardo Rodriguez, off a career-best 2019 season, doesn't become a free agent until after the 2021 season. With so much already tied up in the rotation, Boston could look to sign a starter on a short-term contract, perhaps getting good value on a bounce-back candidate.

Betts turns 27 in October, and he ranks fourth among American League players in on-base percentage and fWAR, trailing Mike Trout, Alex Bregman and Marcus Semien. His .293/.391/.527 doesn't live up to his .346/.438/.640 from his 2018 MVP campaign, when he posted the second-highest fWAR total (higher than any Trout season) since Barry Bonds' 11.9 fWAR in 2004, according to FanGraphs.

Still, since 2014, Trout is the only player to post more WAR than Betts.

Many baseball insiders believe Betts will exceed the average annual value of this past offseason's Bryce Harper and Manny Machado megadeals when he hits the open market, and he could surpass Trout's record $36 million AAV considering the always-steady climb of contract values and inflation.

Betts has given little indication what he'll value more, length or money, once in free agency. Boston wants its star outfielder long term, but along with luxury tax considerations and current salary commitments, its front office is again in flux.

Leading the baseball operations department in Boston has ended with unceremonious departures ever since Henry bought the team in 2002, and for a reason. Expectations start high and never come down. Theo Epstein quit twice (in 2005 on Halloween, leaving Fenway in a gorilla costume, and in 2011 for the Cubs job). Ben Cherington helped bring a World Series to Boston in 2013. Two years later, Boston hired Dombrowski as president of baseball operations in the middle of a game while Cherington still held the GM position. Cherington quit. Dombrowski's Red Sox tenure ended earlier this month when a team spokesman walked into the Fenway Park interview room a few ticks after midnight following a Sunday Night Baseball game against the Yankees and told media members the team was "parting ways" with Dombrowski.

The standard of winning and excellence in Boston keeps rising. National headlines lamented surprise regarding the Red Sox letting go of Dombrowski less than a year after Boston won 108 games, earned buzz as one of the best teams in franchise history and won a World Series title. But 12 championships in 18 years, across all four major sports, changes things, and really quickly.

Winning a World Series isn't enough in Boston anymore. Under previous leadership, largely a remnant of Epstein's time running the organization, the Red Sox melded business and baseball operations. Kennedy, the executive-level face of the franchise, helped build a collaborative culture with Epstein, his childhood friend from the Boston suburb of Brookline. It was a culture that didn't exist under Dombrowski, who by the end of his Red Sox tenure had siloed himself off from much of the front office, mostly receiving advice from senior vice president Frank Wren and special assistant/vice president Tony La Russa.

Boston is now led on an interim basis by the assistant GM trio of O'Halloran, Romero and Scott with senior vice president Ferreira taking on an expanded role -- making her the highest-ranking woman in an MLB front office. Under Dombrowski, O'Halloran focused on player negotiation and day-to-day management in baseball operations, while Romero led international scouting and player development efforts, and Scott oversaw the analytics department. Beyond O'Halloran, Romero, Scott and Ferreira, Boston could look to other familiar faces like Jared Porter and Amiel Sawdaye, who are assistant GMs in Arizona and previously worked in Boston. Their boss, Mike Hazen, ruled himself out of the running by signing an extension to stay with the Diamondbacks.

The tone in Boston brings unique challenges for executives, managers and players.

"Last year, when I came here, I knew what I was getting into obviously," Red Sox skipper Alex Cora said. "The expectations here are to win a championship every year. Is it realistic? No. But as a fan, that's who we are. I'm a fan of other teams and that's what I want for my teams. I don't think it's unfair. It is what it is. We live in a city where the standards are set very, very high since 2002 or right around that. This is what makes it enjoyable, that on a daily basis, you show up and do your best because if not, they're going to let you know that you didn't. That's what pushes me."

Dombrowski's firing amid such an atmosphere didn't change anything for Betts, which shouldn't surprise anyone.

"It doesn't really matter who's there. It's going to be the same answer," Betts said after the Dombrowski news broke. "Nothing's going to change. This is proof that this is a business. I love it here, but definitely it's still a business."

The general manager of the Red Sox, historically, has been among the most scrutinized public figures in the city. Lou Gorman's trade of Jeff Bagwell in 1990 to Houston still intermittently comes up in Fenway Park conversations among fans, writers, security guards and ushers. People still talk about Carl Crawford's and Pablo Sandoval's disastrous tenures in Boston. And the next GM could decide, among many other things, the fate of the team's biggest star.

No pressure.