‘There are a couple of regrets’: Red Sox move forward after Bogaerts bolts Boston
CHAIM BLOOM HAS been reliving the negotiations with Xander Bogaerts in his head.
“There are a couple of regrets,” the chief baseball officer of the Boston Red Sox told ESPN a week after Bogaerts signed with the San Diego Padres.
When Bogaerts landed an 11-year, $280 million deal this month, the question among baseball executives and agents wasn’t whether Boston should have matched San Diego to re-sign its star shortstop, but why Bogaerts even got to free agency in the first place.
When Bloom signed Trevor Story to a six-year, $140 million contract before spring training last year, Bogaerts felt hopeful that an extension on his own contract might follow. One source close to Bogaerts said he would have seriously considered an extension similar to Story’s deal. Instead, the Red Sox offered Bogaerts an additional year and $30 million on top of the three years and $60 million left on his deal. For a player who helped bring championships to Boston in 2013 and 2018 and had grown into the team’s de facto captain, the offer felt like “a slap” according to a source close to Bogaerts.
Bloom and the Red Sox did not want to sign Bogaerts, who would turn 30 before the end of the season, to a contract that would take him into his late 30s and early 40s. But then Bogaerts posted the best season of his career in 2022 by bWAR — his 5.7 the best among all shortstops in baseball — while hitting .307/.377/.456 with 15 homers in 150 games. And when Trea Turner (4.9 bWAR in 2022) signed an 11-year, $300 million deal with the Philadelphia Phillies, the market for shortstops ballooned. Overnight, the price for Bogaerts doubled — and in the end, for what felt like the dozenth time this offseason, the Red Sox were outbid on a player they were pursuing, this one a beloved homegrown star.
Even with the signings of Masataka Yoshida and Justin Turner so far this offseason, two-last place finishes in three years (a span that also includes one American League Championship Series appearance) have elicited questions from fans who want answers not only about the team’s plan to win, but how a front office that preaches building around in-house talent could let go of two of the most accomplished homegrown stars in franchise history — Bogaerts and Mookie Betts, whom Bloom traded to the Los Angeles Dodgers in 2020.
But when asked if there was anything in particular he regrets about the handling of Bogaerts, Bloom declined to share.
“I don’t want to elaborate,” Bloom said. “It’s more private. I don’t want to get into it.”
RED SOX PRESIDENT Sam Kennedy understands why fans are questioning the ownership group’s commitment to winning. As someone who grew up a few subway stops from Fenway Park, Kennedy constantly hears from his parents and the friends of his children about the team’s struggles in 2022.
“You want that passion,” Kennedy said. “You want the talk radio lines lit up.”
Since John Henry led Fenway Sports Group (then known as New England Sports Ventures) in 2001 to buy the Red Sox, the investment firm has grown into an international sports conglomerate that now owns Liverpool FC in the Premier League and the Pittsburgh Penguins of the NHL, with reports indicating Henry’s potential interest in bidding for the Washington Commanders, in addition to FSG partner LeBron James publicly indicating he wants an NBA team in Las Vegas. Kennedy said FSG targets sports teams tied to communities with deep emotional investments in their franchises — and that they spend to win.
But after missing out on Bogaerts, and finishing in second place in many other free agency sweepstakes, Red Sox fans are questioning the owners’ commitment to the team. In truth, those frustrations go all the way back to David Ortiz, who went year-to-year with the Red Sox during the last seasons of his career, and Jon Lester, who received a below-market extension offer in 2014 before being traded to the Oakland A’s.
Four years after trading Lester, Boston would win a World Series in 2018 after signing David Price to a seven-year, $217 million contract, trading a haul of top prospects for Chris Sale and Craig Kimbrel and locking up J.D. Martinez to a five-year, $110 million contract. And that, Kennedy believes, is the real difference in the fans’ responses to the departures of Betts and Bogaerts: the team’s last-place finish in the AL East in 2022.
“It gets frustrating and irritating when you hear [questions] about your commitment to winning,” Kennedy said. “All of our decisions we make are geared towards trying to win a World Series championship. We don’t get those questions when we’re winning.”
After their last World Series win, former president of baseball operations Dave Dombrowski spent big to keep Sale, Martinez and Eovaldi, pushing Boston over the luxury tax threshold. When Betts then asked for a contract valued at $400 million, the Red Sox were unwilling to commit that amount of money, according to multiple league sources. Betts made it clear that he wanted to stay in Boston — he just would not give the team a hometown discount.
The ownership group fired Dombrowski before the end of the 2019 season, less than a year after winning the World Series, and mandated the team cut salary in order to reset the luxury tax penalties. In came Bloom — whom Boston hired from the Tampa Bay Rays — with a vision of creating a Dodgers-style of sustained success, spending big money on star players while consistently developing top prospects to fill out the lineup.
According to multiple sources, Boston’s ownership group did not mandate that Bloom trade Betts to get under the luxury tax. But that is what Bloom ultimately decided to do, with an eye toward increasing the Red Sox’s options in the future. The team traded Betts and Price to Los Angeles for Alex Verdugo, Jeter Downs and Connor Wong. And Betts eventually signed a 12-year, $365 million contract with the Dodgers — a deal he told ESPN in August that he would have accepted in Boston.
Just last week, the Red Sox designated Downs for assignment, admitting defeat on the prospect centerpiece of the Betts deal.
“Have we made wrong decisions in the past? Lots of them,” Kennedy said. “You can’t sit around regretting mistakes of the past. That’s not a good recipe. We respect Mookie and it’s a hard decision, but we’ve moved on.”
But for fans who were told that trading Betts was to create financial flexibility for the future, watching the team get outbid on Bogaerts was the last straw.
With Bogaerts’ production exceeding the team-friendly extension he signed in 2019, the All-Star shortstop planned to exercise the opt-out in his contract after the 2022 season, but he had hoped to play the rest of his career in Boston. He privately expressed to those close to him that he would be willing to eventually move to second or third base if necessary, but he was determined not to accept another team-friendly contract. Like Betts before him, Bogaerts wanted a deal more in line with his perceived value across the sport.
On last season’s Opening Day, Bogaerts expressed his disappointment in not getting an extension done with the Red Sox, and he played out the season knowing he would be a free agent at the end of it.
Bogaerts excelled in 2022, providing one of the few bright spots for a Red Sox team that finished 78-84 and at the bottom of an extremely competitive division. By the end of the season, both Bloom and Kennedy had publicly said signing Bogaerts was their top priority.
Before signing his first extension, Bogaerts told his agent, Scott Boras, that he wanted to stay in Boston. This time, though, he expressed a desire to explore free agency.
“I understand myself better,” Bogaerts told Boras. “I have more of a view of free agency. I want to look into it and see what’s available for me. I want to win, and I want to win now.”
San Diego significantly outbid Boston, and at Bogaerts’ introductory press conference on Dec. 9, he thanked the Padres for being “very straightforward” with him during negotiations.
Boras said Boston’s unwillingness to match the offer from the Padres stemmed from the organization’s evaluation of Bogaerts.
“I can only say that the market for Xander was very different from what their models said,” Boras told ESPN. “But that’s happened before.”
Executives around the sport see the same pattern emerging with Red Sox star third baseman Rafael Devers, who will be 26 at the start of the 2023 season, his last before he becomes an unrestricted free agent in 2024. According to multiple league sources, the Red Sox and Devers are “galaxies apart” in their contract negotiations. The current expectation from Devers and his camp is that the third baseman will be a free agent at the end of 2023, given the current state of contract talks.
Bloom said Boston will make every effort to keep Devers.
“We will probably, I think, go beyond reason to try to get this done,” Bloom said. “Hopefully we can get this done. There are always going to be limitations, like people can just put something plain out of reach. Some people love to bet on themselves and I hope he hits 63 homers if he does that.”
WHILE BOSTON DIDN’T break the bank to sign Bogaerts, the team has given out some large contracts this offseason, signing Japanese outfielder Yoshida to a five-year, $90 million contract while adding Kenley Jansen, Joely Rodriguez and Chris Martin to the bullpen. On Sunday night, the Red Sox also added Turner, a 38-year-old third baseman, on a two-year, $22 million deal. Bloom said the team aimed to add seven to nine players this offseason, and the Red Sox are continuing to explore trades. Additionally, the team is trying to sign players to contract extensions before they hit arbitration, similar to the four-year, $18.75 million contract they gave Garrett Whitlock in April.
If Kennedy is right, and a change in the team’s on-field fortunes will help the fan perception, Boston will need many things to go right that did not in 2022. Ace Chris Sale and center fielder Enrique Hernandez will need to stay healthy. Yoshida will need to produce immediately. Story will need to be more consistent at the plate. The Red Sox will need more contributions from players like Verdugo and Triston Casas, while the rotation will need to lean on Nick Pivetta, Whitlock, Tanner Houck, Brayan Bello and James Paxton, unless Boston adds another starting pitcher. The Red Sox will need to replace the offensive production of Bogaerts in the lineup and his clubhouse presence as a player who spoke both Spanish and English.
As the team builds the roster for 2023, some within the Red Sox front office have questioned Bloom’s decision-making process, team sources told ESPN. One front-office official said Bloom’s deliberate process toward making moves — asking many people for their input before making a decision — can put the Red Sox in a position to fall behind, reacting to other teams versus setting the market.
“I think we have a culture where people can and do express directly to me when they disagree with something,” Bloom said. “We have a lot of people in the loop on transactions that we make and we have a lot of really good debate. We have a place where people can share their opinion and have it be heard.”
Boras said during the negotiations on both Bogaerts and Yoshida that Bloom was “forthright and prepared.”
“Chaim has very defined structure and models that he does for player evaluation,” Boras said.
Executives from other teams question if Bloom can be decisive enough to make big moves to satisfy a rabid, impatient fan base, and whether the approach he built in Tampa will be aggressive enough for a market like Boston.
“I’m not sure how to respond to that,” Bloom said. “I certainly think we’ve made some large commitments in the time I’ve been here. For people who would’ve liked to have seen more, that’s their right. I think a lot of circumstances under which I joined the organization really precluded that for a period of time. I would argue we would’ve been worse off certainly prior to 2021 had we listened to people who wanted to see us make a splash instead of building a good baseball team.”
Boras said Bloom’s aggressiveness varied between Bogaerts and Yoshida.
“For Yoshida, they were very aggressive,” Boras said. “With Xander, they certainly did not meet the standards of what we expected them to do.”
Bloom hears the criticism from the fans, too. When asked about his job status, though, Bloom did not entertain the speculation, saying, “I don’t really worry about that.”
The pressure is on Boston to succeed, but both Bloom and Kennedy know one thing can change the minds of Red Sox fans and earn back their trust: winning.
“There was a lot of talk about our spending in 2022, there was not a lot of talk about our spending in 2021, which was about the same,” Kennedy said. “I think it goes with the wind. If you make the postseason, you’re not going to hear a lot about the spending. If we don’t win, it’s going to be we need to spend, we need to fix things, we need to get better. Winning solves everything.”
The first day of the 2025 MLB draft is complete! The Washington Nationals selected Eli Willits with the No. 1 pick, opting for the prep shortstop — who might be more likely to sign below slot — in a draft with no clear-cut top prospect. And there were plenty of other intriguing selections as the first three rounds unfolded Sunday night.
The Seattle Mariners had to have been thrilled to have Kiley McDaniel’s No. 1-ranked prospect, Kade Anderson, fall to them at No. 3, and Ethan Holliday was selected at No. 4 by his famous father’s former squad the Colorado Rockies.
We asked ESPN baseball insiders Alden Gonzalez, Jesse Rogers and David Schoenfield to break down their favorite and most head-scratching moves of the draft’s first night, as well as to predict which players will bring the most to their new teams in the long term.
A lot of us were thrown for a loop by the first two selections. What do you make of the Nationals taking Ethan Willits at No. 1 and the Angels picking Tyler Bremner at No. 2?
Gonzalez: I was stunned on both accounts. Though there was definitely some uncertainty around the Nationals’ approach, especially since the firing of GM Mike Rizzo, I didn’t see anybody, anywhere, projecting Willits to be their choice at No. 1 overall. But the Angels drafting Bremner was an even bigger risk. Kiley had him 18th in his latest ranking. Six pitchers were ranked ahead of him. But Bremner might be someone who can rise and impact their major league roster quickly, and the Angels are always looking for that.
Rogers: The first two picks really summed up the uncertainty of the entire draft. The Nationals’ faith in a 17-year-old will be tested over the coming years, but the pick will likely save them some money for later in this draft and give Willits time to grow. The same can be said of many of the top picks: They’re going to need time. There are far fewer sure things this year — though Bremner could be the exception. The Angles love to graduate their players quickly, and as a college arm, he could see the majors sooner rather than later. Like Willits, this could also be a cost-saving move for later spending.
Schoenfield: In a draft that not only lacked a sure-thing No. 1 overall pick but was viewed as weaker at the top than those of recent years, it’s perhaps not a huge surprise that the Nationals and Angels used their picks to strike likely underslot deals with Willits and Bremner, giving them money to spend later in the draft — which they can use on high school prospects who might have slipped, trying to buy them out from going to college. It’s a strategy teams have used with success over the years, so the drafts for the Nationals and Angels will have to be viewed in their totality and not just focused on these two players.
What was your favorite pick of the night — and which one had you scratching your head?
Gonzalez: The Rockies have done a lot of things wrong over these last few … uh, decades. But it was really cool to see them take Ethan Holliday at No. 4 after his father, Matt, starred in Colorado for so long. Outside of the top two picks, Ethan Conrad going 17th to the Cubs was my biggest surprise of the night. Kiley had him ranked 30th; others had him falling out of the first round entirely. There’s uncertainty coming off shoulder surgery. But Conrad, 21, put up a 1.238 OPS in 97 plate appearances before his season ended prematurely in March. And the dearth of college bats probably influenced a slight reach here.
Rogers: I’m loving Billy Carlson to the White Sox at No. 10. Though they lost 121 games last season, Chicago couldn’t pick higher than this spot per CBA rules — but the Sox might have gotten a top-five player. Carlson’s defense will play extremely well behind a sneaky good and young pitching staff that should keep the ball on the ground in the long term. Meanwhile, with the pick of the litter when it came to hitters — college outfielders and high school kids as well — the Pirates took a high school pitcher at No. 6. Seth Hernandez could be great, but they need hitting. A lot of it.
Schoenfield: The Mariners reportedly wanted LSU left-hander Kade Anderson all along, but they certainly couldn’t have been expecting to get him with the third pick. (Keep in mind that the Mariners were lucky in the first place to land the third pick in the lottery, so they added some good fortune on top of good luck.) They get the most polished college pitcher in the draft, one who should move quickly — and perhaps make it a little easier for Jerry Dipoto to dip into his farm system and upgrade the big league roster at the trade deadline. Even though I understand why the Angels did it, Bremner still seems a little questionable. With the second pick, you want to go for a home run, and the consensus is that Holliday or even Anderson is more likely to be a more impactful major leaguer. Bremner’s lack of a third plus pitch is an issue, and you have to wonder if the Angels are relying too much on his control — which, yes, should allow him to get to the majors — and ignoring the possible lack of upside.
Who is the one player you’d like to plant your flag on as the biggest steal of this draft?
Gonzalez: Seth Hernandez, who went sixth to the Pirates and should someday share a rotation with Paul Skenes and Jared Jones. High school pitchers are incredibly risky, especially when taken so early in the draft. But Hernandez is a great athlete who already throws hard, boasts a plus changeup and showed improvement with his breaking ball this spring. He’ll go the Hunter Greene route, from standout high school pitcher to major league ace.
Rogers: Jamie Arnold will look like a steal at No. 11, especially when he debuts in the majors well before many of the players taken around him. I’m not worried about the innings drop in 2025 — not when he was striking out 119 hitters and walking just 27. The A’s need to polish him up but will be pleased by how consistent he’ll be. You can’t go wrong with a college lefty from an ACC school — at least, the A’s didn’t.
Schoenfield: I’m going with Billy Carlson with the 10th pick — with the admitted caveat that the White Sox haven’t exactly been stellar at developing hitters. But Carlson looks like an elite defensive shortstop with plus power, and that alone can make him a valuable major leaguer. If the hit tool comes along, we’re looking at a potential star. OK, he’s Bobby Witt Jr. lite? That’s still an All-Star player.
What’s your biggest takeaway from Day 1 of this draft?
Gonzalez: The Nationals throwing a wrench into the proceedings by selecting Willits. It was a surprising choice, but in their minds an easy one. Interim general manager Mike DeBartolo called Willits the best hitter and best fielder available. And in a draft devoid of can’t-miss, high-impact talent, Willits is no doubt a solid pick — a polished hitter who should stick at shortstop and might consistently hit 20 homers and steal 20 bases at a premium position. He also might come under slot, allowing flexibility later in the draft. But his selection is what allowed Anderson to reach the Mariners at No. 3 and prompted the Rockies to draft Holliday at No. 4, among other dominoes. It set a really interesting tone.
Rogers: Things change quickly in baseball. Whereas college hitters are usually the safest bets early in the draft, this year high school position players dominated. (And they all play shortstop, at least for now.) Athleticism has returned to baseball, and draft rooms are acting accordingly.
Schoenfield: I’m agreeing with Jesse. The selection of that many prep shortstops stood out — and they all seem to hit left-handed and run well, and some of them have big power potential and a cannon for an arm. Look, the hit tool is the most important and the hardest to scout and project, so not all these kids are going to make it, but their potential is exciting and, to Jesse’s point, their wide range of tools is showing that baseball is still drawing top athletes to the sport.
The 2025 MLB All-Star Home Run Derby is fast approaching — and the field is set.
Braves hometown hero Ronald Acuna Jr. became the first player to commit to the event, which will be held at Truist Park in Atlanta on July 14 (8 p.m. ET on ESPN). He was followed by MLB home run leader Cal Raleigh of the Seattle Mariners, James Wood of the Washington Nationals, Byron Buxton of the Minnesota Twins, Oneil Cruz of the Pittsburgh Pirates, Junior Caminero of the Tampa Bay Rays, Brent Rooker of the Athletics and Jazz Chisholm Jr. of the New York Yankees.
On Friday, however, Acuna was replaced by teammate Matt Olson.
With all the entrants announced, let’s break down their chances at taking home this year’s Derby prize.
Full All-Star Game coverage: How to watch, schedule, rosters, more
2025 home runs: 17 | Longest: 434 feet
Why he could win: Olson is a late replacement for Acuna as the home team’s representative at this year’s Derby. Apart from being the Braves’ first baseman, however, Olson also was born in Atlanta and grew up a Braves fan, giving him some extra motivation. The left-handed slugger led the majors in home runs in 2023 — his 54 round-trippers that season also set a franchise record — and he remains among the best in the game when it comes to exit velo and hard-hit rate.
Why he might not: The home-field advantage can also be a detriment if a player gets too hyped up in the first round. See Julio Rodriguez in Seattle in 2023, when he had a monster first round, with 41 home runs, but then tired out in the second round.
2025 home runs: 36 | Longest: 440 feet
Why he could win: It’s the season of Cal! The Mariners’ catcher is having one of the greatest slugging first halves in MLB history, as he’s been crushing mistakes all season . His easy raw power might be tailor-made for the Derby — he ranks in the 87th percentile in average exit velocity and delivers the ball, on average, at the optimal home run launch angle of 23 degrees. His calm demeanor might also be perfect for the contest as he won’t get too amped up.
Why he might not: He’s a catcher — and one who has carried a heavy workload, playing in all but one game this season. This contest is as much about stamina as anything, and whether Raleigh can carry his power through three rounds would be a concern. No catcher has ever won the Derby, with only Ivan Rodriguez back in 2005 even reaching the finals.
2025 home runs: 24 | Longest: 451 feet
Why he could win: He’s big, he’s strong, he’s young, he’s awesome, he might or might not be able to leap tall buildings in a single bound. This is the perfect opportunity for Wood to show his talent on the national stage, and he wouldn’t be the first young player to star in the Derby. He ranks in the 97th percentile in average exit velocity and 99th percentile in hard-hit rate, so he can still muscle the ball out in BP even if he slightly mishits it. His long arms might be viewed as a detriment, but remember the similarly tall Aaron Judge won in 2017.
Why he might not: His natural swing isn’t a pure uppercut — he has a pretty low average launch angle of just 6.2 degrees — so we’ll see how that plays in a rapid-fire session. In real games, his power is primarily to the opposite field, but in a Home Run Derby you can get more cheapies pulling the ball down the line.
2025 home runs: 20 | Longest: 479 feet
Why he could win: Buxton’s raw power remains as impressive as nearly any hitter in the game. He crushed a 479-foot home run earlier this season and has four others of at least 425 feet. Indeed, his “no doubter” percentage — home runs that would be out of all 30 parks based on distance — is 75%, the highest in the majors among players with more than a dozen home runs. His bat speed ranks in the 89th percentile. In other words, two tools that could translate to a BP lightning show.
Why he might not: Buxton is 31 and the Home Run Derby feels a little more like a younger man’s competition. Teoscar Hernandez did win last year at age 31, but before that, the last winner older than 29 was David Ortiz in 2010, and that was under much different rules than are used now.
2025 home runs: 16 | Longest: 463 feet
Why he could win: If you drew up a short list of players everyone wants to see in the Home Run Derby, Cruz would be near the top. He has the hardest-hit ball of the 2025 season, and the hardest ever tracked by Statcast, a 432-foot missile of a home run with an exit velocity of 122.9 mph. He also crushed a 463-foot home run in Anaheim that soared way beyond the trees in center field. With his elite bat speed — 100th percentile — Cruz has the ability to awe the crowd with a potentially all-time performance.
Why he might not: Like all first-time contestants, can he stay within himself and not get too caught up in the moment? He has a long swing, which will result in some huge blasts, but might not be the most efficient for a contest like this one, where the more swings a hitter can get in before the clock expires, the better.
2025 home runs: 23 | Longest: 425 feet
Why he could win: Although Caminero was one of the most hyped prospects entering 2024, everyone kind of forgot about him heading into this season since he didn’t immediately rip apart the majors as a rookie. In his first full season, however, he has showed off his big-time raw power — giving him a chance to become just the third player to reach 40 home runs in his age-21 season. He has perhaps the quickest bat in the majors, ranking in the 100th percentile in bat speed, and his top exit velocity ranks in the top 15. That could translate to a barrage of home runs.
Why he might not: In game action, Caminero does hit the ball on the ground quite often — in fact, he’s on pace to break Jim Rice’s record for double plays grounded into in a season. If he gets out of rhythm, that could lead to a lot of low line drives during the Derby instead of fly balls that clear the fences.
2025 home runs: 19 | Longest: 440 feet
Why he could win: The Athletics slugger has been one of the top power hitters in the majors for three seasons now and is on his way to a third straight 30-homer season. Rooker has plus bat speed and raw power, but his biggest strength is an optimal average launch angle (19 degrees in 2024, 15 degrees this season) that translates to home runs in game action. That natural swing could be picture perfect for the Home Run Derby. He also wasn’t shy about saying he wanted to participate — and maybe that bodes well for his chances.
Why he might not: Rooker might not have quite the same raw power as some of the other competitors, as he has just one home run longer than 425 feet in 2025. But that’s a little nitpicky, as 11 of his home runs have still gone 400-plus feet. He competed in the college home run derby in Omaha while at Mississippi State in 2016 and finished fourth.
2025 home runs: 17 | Longest: 442 feet
Why he could win: Chisholm might not be the most obvious name to participate, given his career high of 24 home runs, but he has belted 17 already in 2025 in his first 61 games after missing some time with an injury. He ranks among the MLB leaders in a couple of home run-related categories, ranking in the 96th percentile in expected slugging percentage and 98th percentile in barrel rate. His raw power might not match that of the other participants, but he’s a dead-pull hitter who has increased his launch angle this season, which might translate well to the Derby, even if he won’t be the guy hitting the longest home runs.
Why he might not: Most of the guys who have won this have been big, powerful sluggers. Chisholm is listed at 5-foot-11, 184 pounds, and you have to go back to Miguel Tejada in 2004 to find the last player under 6 foot to win.
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