When Mookie Betts came along and began to establish himself as one of the game’s great stars, the Red Sox couldn’t come to a long-term agreement with their face of the franchise and eventually traded him away.

The Red Sox made sure not to repeat that mistake with Roman Anthony.

Less than two months into his big league career, the Red Sox locked up Anthony to an eight-year, $130 million extension that will keep him under club control through the 2034 season. The two sides began negotiating as soon as the trade deadline passed and within days reached an agreement that will ensure Anthony remains a franchise cornerstone throughout the next decade.

After watching Betts, Xander Bogaerts and eventually Rafael Devers all move on, fans can rest easy knowing Anthony isn’t going anywhere for a long time.

Anthony is now the third young standout the Red Sox have signed to a long-term extension who had less than a year of service time at the time the deal was announced, joining teammates Ceddanne Rafaela and Kristian Campbell. Such deals are becoming more commonplace around baseball, and it isn’t hard to see the appeal.

The player gets lifetime financial security along with a significant raise in earnings over the first six years of their career, and in exchange the team gets a couple of extra years of team control beyond the point where the player otherwise would have reached free agency.

If the player develops into a star, those last couple of years could turn out to be huge bargains. But on the flip side, if the player flames out the contract could age poorly.

Because Anthony is only 21, he has the added benefit of being able to sign an eight-year extension with a club option and still hit free agency at around age 30, the point when most players typically hit the open market. So even if he outplays his current contract, he’ll still be in line to eventually land a much larger deal down the road.

How does Anthony’s contract stack up against others who signed big deals at a similar stage of their career?

Seattle Mariners' Julio Rodriguez holds the trident while celebrating his three-run home run against the Chicago White Sox during the second inning of a baseball game Wednesday, Aug. 6, 2025, in Seattle. (AP Photo/Lindsey Wasson)Seattle Mariners outfielder Julio Rodriguez currently holds the record for largest contract signed by a player with less than one year of MLB service time. (AP Photo/Lindsey Wasson)

In terms of guaranteed dollars, Anthony’s $130 million deal is the third largest in history signed by a player with less than a year of MLB service time, behind Julio Rodriguez (14 years, $210 million) and Wander Franco (11 years, $182 million), who will likely earn far less depending on how long he spends on the restricted list due to his ongoing legal troubles.

It is larger than the deals signed by Corbin Carroll (eight years, $111 million), Ronald Acuña Jr. (eight years, $100 million) and Jackson Chourio, who hadn’t even made his MLB debut when he signed his eight-year, $82 million deal at the 2023 Winter Meetings.

It is more than twice the value of the deals signed by teammates Rafaela (eight years, $50 million) and Campbell (eight years, $60 million).

The most comparable deal to Anthony’s, even though he had slightly more than a year of service time already at the time of his extension, is likely the one signed earlier this year by Jackson Merrill.

San Diego Padres' Jackson Merrill watches his two-run home run during the fourth inning of a baseball game against the Cleveland Guardians 307Wednesday, April 2, 2025, in San Diego. (AP Photo/Gregory Bull)San Diego Padres outfielder Jackson Merrill is only a year older than Red Sox rookie Roman Anthony and recently signed a similarly lucrative contract extension. (AP Photo/Gregory Bull)

After making San Diego’s 2024 Opening Day roster about a month shy of his 21st birthday, Merrill posted a monster rookie season in which he batted .292, hit 24 home runs, tallied 90 RBI, stole 16 bases and had an .826 OPS. He was named an All-Star, won a Silver Slugger and finished second to Pirates ace Paul Skenes in the Rookie of the Year vote.

This April, still at age 21, Merrill signed a nine-year, $135 million extension with the Padres.

Anthony is almost exactly a year younger than Merrill, and while he’s made a strong impression since his call-up, he hasn’t been as productive as a rookie as Merrill was. Still, he’s shown enough to convince the Red Sox to make a huge investment in his future, and now he owns his own similar contract after just 59 days in the majors.

If Anthony turns into anything close to the level of player that Rodriguez, Carroll, Acuña and Merrill are, then the Red Sox future will be in great hands.

Baltimore Orioles runner Colton Cowser (17) scores against Boston Red Sox catcher Connor Wong during the second inning of Baltimore's 6-1 victory Wednesday in Baltimore. (AP Photo/Nick Wass)The Red Sox have 15 games remaining against teams that are currently in last place, including six against the Baltimore Orioles. (AP Photo/Nick Wass)
Road gets easier

The second half hasn’t been kind to the Red Sox in recent years, and this season the club faced its toughest stretch of the schedule coming out of the All-Star break.

But now the Red Sox are nearly out the other side, and to this point they’ve passed their biggest test with flying colors.

From the All-Star break up to this weekend’s series in San Diego the Red Sox played 12 of 18 games against clubs with winning records, including four current division leaders. Over that stretch the Red Sox went 11-7, including a seven-game win streak that included a three-game sweep of the AL West-leading Houston Astros.

The Red Sox aren’t out of the woods yet: they still have to finish this weekend’s series against the Padres and right after will be a road date with the Astros, but the schedule will start to lighten up from there on out.

Starting Monday, 24 of Boston’s last 43 games will be against teams that entered the weekend below .500. That includes 15 games against last-place teams, including six each against the Orioles and Athletics plus three against the Pirates. The Red Sox also have series against the Marlins, Diamondbacks and Rays on the schedule.

With the club already in strong playoff position, those series will serve as prime opportunities to keep stacking up wins.

This week’s series at Houston will be the last time the Red Sox see a first-place team until the final week of the season, but in the meantime they will have two more series against the Yankees, who have been in free fall over the past two months but who just got Aaron Judge back from the injured list.

The Red Sox will have their work cut out for them at the end, with back-to-back series against the American League’s top two teams in the Blue Jays and Tigers to wrap up the regular season. Those will be tough, but the upside is that if the Red Sox take care of business beforehand they could go into those matchups with an opportunity to not only win the AL East title, but possibly also lock up home field advantage throughout most of the playoffs.

Oldtime Baseball Game

The 31st annual Oldtime Baseball Game will be held on Wednesday, Aug. 20 at St. Peter’s Field in Cambridge, and this year’s event will once again partner with The Boston Home, a nonprofit residence and resource for adults with advanced neurological disorders, primarily multiple sclerosis.

This year’s game will honor longtime Red Sox vice president of scouting, development and integration Gus Quattlebaum, who was diagnosed with primary progressive MS in 2021.

Founded in 1994, the Oldtime Baseball Game features college and high school players from throughout the area wearing throwback uniforms representing every era of baseball history. Former Red Sox All-Star Brock Holt will play in this year’s game wearing the uniform of the 1920s Chicago American Giants, an old Negro League club. The same uniform was worn by the late Tim Wakefield when he pitched in the 2018 game.

The game also includes two Red Sox uniforms worn by the late Jim Corsi, who played in the Oldtime game in 2002 and 2003. One of those will be worn by Corsi’s son Joey, who is playing in the Oldtime game for the fourth straight year.

Admission to the Oldtime game is free and the pregame program is scheduled to begin at 7 p.m. In the event of rain the makeup date will be Thursday, Aug. 21 at 7 p.m., and more information can be found at oldtimebaseball.com and thebostonhome.org.