It would have been unthinkable 25 years ago to picture what was coming. Back then, the Curse of the Bambino was still a thing. Jayson Tatum still had baby teeth. Mike Vrabel and Don Sweeney still played defense.
The Fleet Center was new and the Red Sox were still considering a replacement for Fenway Park. After decades of disappointment, all the success, all the drama and the 13 championships that would follow would have been unimaginable.
So making predictions about the next 25 years is probably a little foolhardy, but it’s a lot of fun.
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Patriots quarterback Drake Maye greets Celtics forward Jayson Tatum (Photo by Barry Chin/The Boston Globe via Getty Images)Boston Globe via Getty Images
Using conversations with people in the city and on our staff and a few fun arguments with each other, we created a list of 25 people who’ll be in a position to influence and impact what lies ahead for the next 25 years in our sports-loving region.
We have athletes, coaches, front office personnel, owners and a couple of wild cards.
We kept our criteria largely open with a few exceptions. The people we chose are people who will impact Boston sports teams and events.
AJ Dybantsa, the BYU star from Brockton who is expected to be a high draft pick, could become an NBA superstar. But it’s unlikely to be with the Celtics, so he and other stars-to-be with local ties are not on the list.
Without further ado, here are the 25 for the next 25.
25. James Hagens
Boston College vs. Maine Men's Hockey
James Hagens (Photo: Katie Morrison-O’Day)Katie Morrison-O'Day
Looking back in 25 years, the Bruins’ top prospect might be way too low on this list. He’s one of the best prospects in all of hockey and if he can be the No. 1 center he’s projected to be, the Bruins’ return to contender status can get sped up drastically.
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24. Michael Felger
Felger
The Sports Hub's Michael Felger (Photo by Matt Stone/MediaNews Group/Boston Herald via Getty Images)MediaNews Group via Getty Images
He’s the driving engine of the most successful show on the most successful station in the market. Felger is polarizing, but his opinion influences not only the fans, but the teams around the city.
23. Cathy Engelbert
Cathy Engelbert
WNBA Commissioner Cathy Engelbert (AP Photo/Patrick Semansky, File)AP
Boston wants a WNBA franchise. The WNBA commissioner is on this list because she’ll have a huge role in determining whether that can happen.
It’ll be interesting to see if Engelbert stays in the job after what could be a contentious labor fight upcoming. But for now at least, she’s the one wielding the power.
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22. Maura Healey/Michelle Wu
Maura Healey, Michelle Wu
Governor Maura Healey with Mayor Michelle Wu (Chris Van Buskirk/MassLive)
Within the next 25 years, there will likely be talk of rebuilding, replacing or renovating Fenway Park. There are already rumblings about a new basketball arena or a joint Celtics/Bruins arena and plenty more fights to be had over soccer stadiums.
Whether or not the WNBA comes to Boston will remain an issue. Boston/Massachusetts both figure to keep bidding on national and international sporting events, too.
All of these things require political influence. Healey, the governor of Massachusetts and Wu, the mayor of Boston, could be very influential. But there’s no guarantee that these two will be in their current roles for that long. Either could get voted out or they could run for Senate, or become cabinet secretaries under the next democratic president.
Or if they follow in the footsteps of their respective predecessors, they could be the head of the NCAA and the head of the NHL Players Union.
21. Bill O’Brien
Clemson Boston College Football
Boston College coach Bill O'Brien (AP Photo/Mark Stockwell)AP
This is a critical time in Boston College football. Over the next few years, college sports — driven by big conference football — look likely to continue to evolve, behind the increasingly powerful influences of the playoff, conference movement, NIL and transfer rules. When the dust settles, will BC still be with the big boys? O’Brien’s success or failure can influence that.
20. Joe Mazzulla
Knicks Celtics Basketball
Boston Celtics coach Joe Mazzulla (AP photo: Charles Krupa) AP
Mazzulla was hard to place on this list. The Celtics’ quirky, unique coach has shown himself to be well-suited for this market. At the same time, his style is volatile and expectations are high. He could win another title. He could get fired in 2026-27. Either way, his future influences the Celtics’ future.
19. David Pastrnak
Toronto Maple Leafs v Boston Bruins
Bruins wing David Pastrnak (Photo by Brian Babineau/NHLI via Getty Images)NHLI via Getty Images
Given the way scoring wingers age, at 29, Pastrnak probably has quite a few good years left in him. If he stays healthy, he’ll likely make a run at the Bruins’ career goals record and could finish pretty high on the NHL career list, too.
18. Alex Cora
Alex Cora
Red Sox manager Alex Cora (AP Photo/Gerald Herbert)AP
Cora is very impactful on the Red Sox in the present, but he’s said he doesn’t picture himself as a lifer in the manager’s office.
“I don’t see myself managing as long as (Terry Francona), Tony (La Russa), Mike Scioscia, those guys,” Cora said in 2022. “I respect them, but it’s very hard. Can you imagine managing in Boston for 20 years doing this? It’s not easy.”
He could always change his mind — lest we forget Bill Belichick’s Marv Levy comment — but Cora is currently entering his eighth season as Sox manager already.
17. Eliot Wolf/Ryan Cowden
Eliot Wolf
Patriots EVP of Player Personnel Eliot Wolf (Photo: Nick O'Malley)(Nick O'Malley, MassLive)
Within the triumvirate of Wolf, Cowden and Mike Vrabel, it’s tough to know who deserves the most credit for the 2025 offseason, but the Patriots front office did an excellent job.
In Milton Williams, Stefon Diggs and Robert Spillane, they landed a slew of impactful free agents and then nailed the draft, too. It’s led to a far faster turnaround than anticipated.
16. Marco Sturm
Rangers Bruins Hockey
Bruins coach Marco Sturm (AP Photo/Mark Stockwell)AP
Sturm has gotten off to a solid start in his first season as an NHL head coach. If it continues, his structure-centric defensive style will dictate not only how the Bruins play, but how they build their roster and make personnel moves going forward.
15. John Streicher
Stretch
Patriots VP of football operations and strategy John "Stretch" Streicher (Photo: Nick O'Malley) (Nick O'Malley/MassLive)
Streicher isn’t as well-known as some of the others on this list, but Mike Vrabel’s right-hand man owns the title of vice president of football operations and strategy. From game-day challenges to personnel evaluation, “Stretch” has a hand in pretty much everything Vrabel does.
He’s this high because of the expectation that his role will continue to grow over the next several seasons and could eventually grow into a general manager’s role.
“He’s meant a lot to the success that we had in Tennessee,” Vrabel said. “His growth, in this business of NFL football, the connections that he makes with our staff and our players, and they know that he’s an extension of me.”
14. Jaylen Brown
Celtics 76ers Basketball
Celtics wing Jaylen Brown (AP Photo/Chris Szagola)AP
One of the hardest players to rank on this list. He’s a great player in the prime of his career. Presuming he stays healthy and stays in Boston, he’s headed for all-time great Celtic status with a retired number, etc.
If Jayson Tatum’s injury starts a run of health problems, then Brown could become the alpha and would belong much higher. There have always been rumors that he doesn’t want to stay in Boston long-term. If he leaves, he should obviously be lower. Those rumors often came from the same places as the rumors that he and Tatum had friction between them and those seem to have dissipated.
13. Charlie Jacobs
Charlie Jacobs
Boston Bruins CEO Charlie Jacobs. (AP Photo/Charles Krupa)AP
Since the NHL put in a salary cap, the Bruins have spent to it, and the Jacobs family has largely stayed out of day-to-day hockey issues. But this offseason, he chose to stick with Cam Neely and Don Sweeney to lead the team’s rebuild/retool. At some point in the not-too-distant future, he’ll face arena questions too.
12. Robert Kraft
New England Patriots
Patriots owner Robert Kraft (Photo: Nick O'Malley) (Nick O'Malley, MassLive)
Undoubtedly one of the most impactful figures of the last 25 years, Kraft has his team in an excellent spot with an eye toward the future. The Patriots were valued at $9 billion earlier this year as the 84-year-old sold 8% of the franchise.
A Hall of Fame finalist, Kraft could wind up in Canton as soon as next summer.
11. Garrett Crochet
Garrett Crochet
Red Sox ace Garrett Crochet (Photo by Daniel Shirey/MLB Photos via Getty Images)MLB Photos via Getty Images
The 26-year-old lefty is the definition of an ace.
Major League Baseball’s strikeout leader in 2025, Crochet should just be entering his prime, which is wonderful news for Red Sox fans. The AL Cy Young runner-up brought a dominance to the mound at Fenway Park that hasn’t been seen in years.
10. Don Sweeney
Don Sweeney
Bruins general manager Don Sweeney. (AP Photo/Mary Schwalm)AP
When the Bruins approved his teardown of the team’s core last year, they handed the general manager the keys to shape the franchise for the foreseeable future. His success or failure and the speed at which it happens will define the next chapter of the Bruins going forward.
9. Roman Anthony
Roman Anthony
Red Sox outfielder Roman Anthony (AP Photo/Stephanie Scarbrough)AP
The No. 1 prospect in baseball cracked the majors at 21 years old and lived up to the hype until his rookie season was derailed by an oblique strain. Though he only played 71 games, Anthony still finished third in the AL Rookie of the Year voting.
With an eight-year extension signed in August, Anthony is under team control through 2034 and his emergence has given Craig Breslow even more avenues to be creative. It’s far easier to deal a different player from Boston’s outfield surplus because Anthony rocketed through the minors and looked like a foundational piece so quickly.
8. Jayson Tatum
Jayson Tatum
Celtics forward Jayson Tatum. (AP Photo/Frank Franklin II, File)AP
How close he gets to what he was before and how fast he gets there will determine a lot about the Celtics’ immediate future.
If he quickly returns to full Jayson Tatum, he’s a 27-year-old (turns 28 in March) elite player who will be the centerpiece of their quest for Banner No. 19. If he’s not the same or is now injury-prone, his massive contract will be an albatross.
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7. Craig Breslow
Craig Breslow
Red Sox Chief Baseball Officer Craig Breslow (Photo by Danielle Parhizkaran/The Boston Globe via Getty Images)Boston Globe via Getty Images
With a fully-stocked farm system and a Major League roster on the cusp of contention, there are quite a few ways Breslow could make Boston better now and potentially down the road.
Even if Breslow winds up as John Henry’s latest head executive fired after four years — Ben Cherington (2011-15), Dave Dombrowski (2015-19), Chaim Bloom (2019-23) — moves he makes now can have lasting ripple effects. Dealing Rafael Devers last June will impact the Red Sox for the next decade.
Whether that’s a positive or negative impact depends on what else Breslow does.
6. Mike Vrabel
Mike Vrabel, Drake Maye
Patriots coach Mike Vrabel and quarterback Drake Maye. (AP Photo/Greg M. Cooper)AP
In his first season at the helm in Foxborough, Mike Vrabel has been more than a coach. He’s looked like a program builder.
A former player himself, Vrabel excels at making concepts digestible for his team, and a culture has formed quickly. His two non-negotiable demands — effort and finish — show up on New England’s tape every week and it’s led to a quicker turnaround than even the most optimistic fans imagined.
With Vrabel running the show and Drake Maye at quarterback, the Patriots are in the best position of anybody for the next quarter-century.
5. Bill Chisholm
William Chisholm
New Celtics owner Bill Chisholm. (Courtesy photo: William Chisholm Investor Group) Courtesy of William Chisholm Investor Group
The new Celtics owner is the ultimate wild card. The only significant thing he’s done so far is write a really big check. He’s saying all the right things. But he’s largely a mystery.
Will he be willing to spend to turn a great team into a championship contender? Will he someday be the driving force for building a new arena? Will he be a possible WNBA owner too? Will he have a productive relationship with Brad Stevens?
4. John Henry
John Henry
Red Sox principal owner John W. Henry (Photo by James Baylis - AMA/Getty Images)Getty Images
With no salary cap in Major League Baseball, there’s truly no position more impactful in Boston sports than Red Sox owner, but because it’s unknown how long Henry will keep the team, he lands at No. 4.
The 76-year-old helped bring four World Series championships to Boston from 2004-18, but the Sox haven’t shown the same commitment to spending since Henry fired Dave Dombrowski. Instead of paying Mookie Betts, they traded the homegrown star, and more recently jettisoned Rafael Devers and his contract in a stunning deal last June.
With the Sox appearing on the cusp of real contention, will Henry recommit to spending like a powerhouse?
3. Drake Maye
Giants Patriots Football
Patriots quarterback Drake Maye (AP Photo/Charles Krupa)AP
The 23-year-old quarterback is the highest-ranked player on the list, and for good reason: It looks like the Patriots hit the jackpot with Maye.
There isn’t an obvious weakness in Maye’s game right now, and he’s threatening for an MVP award in just his second season. Maye has one of the NFL’s best deep balls, he’s been incredibly accurate on underneath throws, and he’s athletic enough to burn defenders with his legs, too. Thanks to some shepherding from Josh McDaniels, Maye’s decision-making has been sharp for a quarterback with less than 30 NFL starts on his resume.
Nobody is ever going to match Tom Brady’s run in Foxborough, but with Maye, Patriots fans can be justified in feeling like they’ve found their franchise quarterback of the future.
2. Brad Stevens
Brad Stevens
Celtics president of basketball operations Brad Stevens (AP Photo/Michael Dwyer)AP
Stevens is one of the most respected personnel men in the sport.
He’s made smart draft choices and shrewd trades to help construct one championship roster only to have to tear it down to avoid second apron luxury tax penalties.
Stevens’ moves have already made the 2025-26 Celtics better. He’ll have Tatum coming back and more financial flexibility a year from now, leaving Stevens in position to set the course for the next decade.
His legacy and the Celtics’ immediate future will be determined by what happens next. If he’s successful, he’ll be making a case for Hall of Fame enshrinement.
1. Jonathan Kraft
Patriots
Patriots president Jonathan Kraft (Photo: Nick O'Malley) (Nick O'Malley, MassLive)
Almost every Patriots fan can recognize Jonathan Kraft. They see him every Autumn Sunday, sitting with his father in the owner’s suite.
But they don’t really know him. Robert Kraft has been the face of the Patriots’ ownership, while the scope of Jonathan’s influence isn’t clear.
While Robert Kraft has been one of the NFL’s most influential, powerful and stable owners, at 84, he’s likely to hand the reins to his son sooner rather than later.
Jonathan Kraft will try to maintain the Patriots’ influence throughout the league while keeping them elite on the field.
It’s not just the Patriots. Soccer is likely to boom again after the World Cup. Can he use that to help the Revolution’s popularity increase or finalize a new soccer-only venue closer to Boston?
In 2050, we might kick ourselves for not including:
More women — Between the Boston Fleet, the Boston Legacy FC and the likely eventuality of a WNBA team, the next 25 years will likely see women’s sports play a larger role in Boston than ever before as interest continues to grow. There will be star players, key executives, coaches and owners. But in 2025, we’re at an early crossroads. Some of those impactful people might be here already. Some of them might currently still be in middle school. Twenty-five years is a long time.
Jeremy Swayman — A good case could have been made for Tuukka Rask to be among the most impactful players of the last 25 years. Swayman could have a similar case.
Marcelo Mayer/Kristian Campbell — Neither Red Sox prospect has looked like the future stars the team was hoping they’d be yet. Mayer’s ceiling looks much higher. Campbell’s impact may be as a cautionary tale of committing to a prospect after a good couple of weeks.
Donald Trump — The president likes sports and has aggressively tried to influence the debate. He successfully pushed baseball to reinstate Pete Rose. So when baseball has its expected labor stoppage in 2027, it wouldn’t be surprising to see him stick his nose in. However, that gets resolved, it could drastically impact the Red Sox.