Confidence rankings for Boston's four general managers building a winner

With all four of Boston's professional teams in some form of a build/rebuild/reboot, we thought it would be an interesting exercise to ask our analysts and insiders to rank their level of confidence in each general manager being able to build a championship roster.

Spoiler alert: The results were far from unanimous. 

John Tomase

1. Chaim Bloom, Red Sox

No sport places a greater value on prospects than baseball, where years in the minor leagues only heighten the anticipated arrival of The Next Big Thing.

It is fitting then, that my choice for Boston's leader best positioned to return his team to glory is himself a prospect.

Red Sox chief baseball officer Chaim Bloom just turned 38 and is in his first full season at the helm. While he's the only one of Boston's four major architects who has yet to build a champion, he has already shown in a little over a year on the job that he is patient, smart, and unlike anyone else on this list, on the cutting edge of his game's trends.

Like a bicycle tire on the lowest gear that requires some effort to spin but quickly gains speed, Bloom's early moves have created momentum that should only grow. Trading closer Brandon Workman to the Phillies for starter Nick Pivetta and prospect Connor Seabold is already a steal. He turned an outfielder in Andrew Benintendi who had just hit .113 into five prospects. The Red Sox farm system is poised to start climbing the prospect rankings after years of neglect.

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What Bloom hasn't done yet is what comes next -- spending money. The combination of a strong farm system and massive resources is how World Series winners are made, and the Red Sox are on their way. He'll soon remove Dustin Pedroia, David Price, and Nathan Eovaldi from the books, which means he'll soon be sitting on a pile of cash.

It is already abundantly clear that Bloom has a plan, which befits his time building a winner on a shoestring in Tampa. The Boston version will eventually include superstars, and I'm buying his vision.

2. Bill Belichick, Patriots

Belichick's greatness as a coach covers some sins as a general manager. How he squeezed seven wins out of last year's mess, for instance, qualifies as a minor miracle. In a league built around speed and versatility, however, Belichick's Pats feel plodding and slow. He has adjusted with the times before, and we should have faith that he'll do so again.

3. Don Sweeney, Bruins

Say what you want about the Bruins' aging core defying Father Time, but it's not all about veterans Patrice Bergeron, David Krejci, Brad Marchand, and Tuukka Rask. On Sweeney's watch, David Pastrnak has blossomed into an elite scorer, Charlie McAvoy has grown into a No. 1 defender, and Anaheim castoff Nick Ritchie has become a power play machine. The Bruins are well-positioned financially to make a deadline move, too.

4. Danny Ainge, Celtics

This is a concession to the limits of his sport. Rebuilding in the NBA requires either cap space or draft picks, and right now Ainge possesses neither. Kemba Walker's max contract will be a drag on the franchise for two more seasons and Ainge has little ammunition to upgrade around the Jays. Outside of the Gordon Hayward trade exception, he has tied his own hands, and that's scary.

Tom E. Curran

1. Danny Ainge, Celtics

How many times has Ainge made something out of nothing since 2006? Three. After the 2006-07 Celtics went 24-58, he landed Kevin Garnett and Ray Allen to join a not-very-enjoyable superstar in Paul Pierce. They won a title the next year. They wrung another Finals appearance from them then, when it was over with Big Three 2.0, he orchestrated another reboot with the Brooklyn trade.

He brought Brad Stevens in from Butler. If you’re weary of Stevens’ approach, you’re missing that he’s been very, very solid, succeeding when so many other college coaches haven’t in making the jump.

During Stevens’ tenure, Ainge has kept on trying to make the boldest moves possible to remain near the top of the Eastern Conference. Isaiah Thomas, Al Horford, Aron Baynes, Jae Crowder, Daniel Theis, Marcus Morris, Jonas Jerebko and others were key acquisitions who were useful to outstanding front-line players. He took a big swing when IT was fading and got a great player in Kyrie Irving. When that didn’t work, he got the best available replacement in Kemba Walker. He went out and got Gordon Hayward. What happened with him is a little beyond Ainge’s control.

Meanwhile, he hit with Marcus Smart, Jaylen Brown and Jayson Tatum in the top 10. The fact is, in a star-driven league, Ainge has continually found a way to land them when the Celtics needed them. And while they’re flagging a bit right now, they have two outstanding young players under contract to be franchise building blocks over the coming seasons. Ainge has proven he can do this and I’d confidently bet on him doing it again.

2. Bill Belichick, Patriots

The Patriots roster aged and declined over the last half of the 2010s. They are now a team without a starting quarterback. The wide receivers and tight ends they finished the year with in 2020 couldn’t start for any other team. They don’t have a lot of firepower in their front seven. Their linebacker group is developing and their secondary is aging.

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This, Belichick indicated in September, was a by-product of going all-in to win with Tom Brady under center. Belichick’s set up now with cap space and draft picks to create a post-Brady Patriots team that takes a hammer to the notion that Brady was the engine that made the Patriots go. Even with all the misses he’s had the past half-decade, it would be an affront to what we’ve seen since 2000 to say Belichick can’t make it happen.

3. Don Sweeney, Bruins

The Bruins GM was named GM of the Year in 2018-19. Since taking on the job for Peter Chiarelli in May of 2015, he’s kept the Bruins core intact while also making the hard moves to say goodbye to players (Zdeno Chara) that the team had to move on from. Sweeney’s labored to find high-end talent but he’s succeeded in making sure the Bruins have the finances right to keep themselves in the game to keep hunting it.

4. Chaim Bloom, Red Sox

Given how competitive Bloom helped make a low-budget team when he was in Tampa, it will be interesting to see how competitive he can make a big-budget team in Boston. But the guy hasn’t even had a shot to start building yet. The Betts trade wasn’t his fault. That was an ownership edict. And getting out of David Price’s contact while bringing back Alex Verdugo and Jeter Downs is a W.

Meanwhile, a cheating scandal cost him his manager before last year began and then came a pandemic. I have him last in line because he hasn’t had long enough to render an fully developed opinion on. But I don't hate it.

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Chris Forsberg

1. Danny Ainge, Celtics

Let’s be clear here: Ainge landing the top spot on our list isn’t necessarily a reflection of the current confidence meter. He was on an absolute GM heater from the Brooklyn blockbuster in 2013 through the Kyrie Irving deal in 2017. But, in part because of how the Irving situation fizzled and some missteps since that point, the team hasn’t quite made the final leap to surefire title contender that we probably expected by this point.

Fortunately for Ainge, he doubled his MLB career home run total (2) by hitting NBA home runs with Jayson Tatum and Jaylen Brown. And his basketball batting average is way above his .220 mark with the Blue Jays, so there should be confidence that he can bust his own recent slump. A couple extra-base hits moving forward, particularly with the Gordon Hayward trade exception, could position Boston to make a true run at Banner 18.

What’s more, the Celtics will be in position to pair another star with the Jays whenever Kemba Walker comes off the books, and their window to chase titles could be open for a half decade or more with the right moves.

2. Don Sweeney, Bruins

He’s got David Pastrnak and a bunch of playoff-tested vets, which seemingly gives the Bruins a chance to be in the title conversation. But, to be quite frank, his lofty spot is more a function of the fact that the lift simply doesn't seem as daunting as the gents behind him here.

3. Chaim Bloom, Red Sox

We like the flexibility that Bloom has created for the rebuilding Red Sox. In the bigger picture, we think he’s exactly the forward-thinker the Sox need at that spot. Will that translate to being competitive this year? Probably not.

But at least the Sox can take stock of their assets and won’t be stuck in baseball purgatory because they signed a bunch of bad deals and gutted the farm system.

4. Bill Belichick, Patriots

We have full confidence in Belichick at the helm (well, except maybe drafting wide receivers) but until the Patriots figure out how to get their next star quarterback, we’re not very bullish on this team’s chances to get out of the AFC while Patrick Mahomes is scrambling around.

Phil Perry

1. Bill Belichick, Patriots

This a trick question? Of this quartet, is anyone deserving of more confidence than the architect of six championship teams? Someone who made the final four 13 times in 21 tries?

This can't be all about track record. If it was, the argument would be brief. But it isn't. Belichick has reset his salary cap, and he owns six picks in the first four rounds. He has promising pieces in the secondary and on the offensive line. He can buy talent over the course of the next few seasons -- no team has fewer cap commitments than the Patriots in 2022 or 2023 -- and his recent draft-day luck seems due to right itself.

He's a team-building chameleon, having constructed champions with stifling defenses, explosive passing attacks and punishing running games. He's built winners through free agency, the draft and with trades. He remains one of the game's best minds. Now it's time for him to pull every lever as he gets to work on the next iteration of his roster following an unprecedented run. One could argue he should be the most motivated general manager in town.

The post-Tom Brady quarterback question is massive, no doubt, but let's see how Belichick answers when he has money to play with and pulls the trigger before June. If there's no deadline -- the question here is not, "Who wins a title next?" -- the choice is easy. Who's deserving of more confidence than Belichick, even at 69, with a long runway? Don't overthink it.

2. Danny Ainge, Celtics

Two young, uber-talented star players? Check. Talent around those stars? Not exactly. Championship chemistry? Stop it. Plenty of work here for Ainge to earn ring No. 2 since taking over in 2003 -- even if he's seemingly halfway there from a roster-building standpoint.

3. Chaim Bloom, Red Sox 

Bloom showed he knew what he was doing when it came to talent development in Tampa Bay. And while he'll have more money to play with in Boson, he's a long way from Tampa now. The expectations are different. The pressures are different. Confident he's a smart baseball mind? Sure. Confident that he'll have the Red Sox back in championship contention? That's another story.

4. Don Sweeney, Bruins

The Bruins aren't in a bad spot. But they aren't in a legitimate championship-contending spot, either. Unfortunately for Sweeney, he'll have to make the most of their transition from one core to the next. And it doesn't look like they'll overlap long enough or successfully enough to be considered among the league's best.

DJ Bean

1. Bill Belichick, Patriots

It feels insane putting arguably the worst GM of this group at the top of the list, but you can't avoid all the circumstances when determining which GM will fare the best. One major consideration is that Belichick only needs a good, not great, roster to get back to winning. Think about it: Belichick the coach got seven wins out of that horrible 2020 Patriots roster. That was a failure as a GM, given that the Patriots should be picking higher, but it tells you that Belichick the coach is a major ace up the sleeve of Belichick the GM.

All that said, this is still going to take time. This offseason will be the first step. Belichick's good at finding guys who have been in the league for a few years and tapping into something their last team might not have (Kyle Van Noy, Mike Vrabel a zillion years ago). As such, he can use free agency or trades to fill in some of the holes, but these next couple of drafts are especially important. He's got to find the quarterback of the future at some point, and if they end up being good, he's going to have to do something he wouldn't with Brady for so long: pay him what he's worth.

2. Don Sweeney, Bruins

I don't think Don Sweeney is a great GM. He isn't very good at drafting and he's had some nearly catastrophic moves in free agency (David Backes, Matt Beleskey) and trades (Jimmy Hayes). His biggest moves have been re-signing players already on the team on good contracts (Brad Marchand, David Pastrnak) and selecting Charlie McAvoy.

But, as is the case with Belichick, I can't ignore his team's situation. The Bruins are a paper tiger, but they're closer to getting to a championship than any team in town right now. So Sweeney has less work to do. If this is going to be the year, he needs to add at least a scorer and a defenseman.

3. Danny Ainge, Celtics

This is unfortunate timing for Ainge, because we're writing this when his stock couldn't be lower. Ainge is a good GM, but he's had a rough couple of offseasons. He's got a duo other teams in the league would kill for, but he needs to actually build a team around them. We've overlooked that.

4. Chaim Bloom, Red Sox

This isn't even a slight to have him here. The Red Sox are expected to be bad, so anything Bloom does with the team is found money. Hopefully he becomes known for something better than the Mookie Betts trade.

Here's the final tally, with Belichick (barely) earning top honors: