What Is the Best GM-Coach Tandem in Boston?

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With the offseason in three of the four major Boston sports teams well underway, management is under considerable scrutiny. Even in baseball, with the trade deadline fast approaching Dave Dombrowski is under fire. This begs the question—who is the best GM-Coach duo in Boston sports?

Ranking the different sports is definitely hard, so there are several key categories that are able to be graded across the four major sports—drafting, coaching, free agent signings, and trades.

Championships are excluded because coaches like Alex Cora were still playing when Bill Belichick was winning his first Lombardi Trophy. However, competition will be considered because some teams have cakewalks in terms of roads to the playoffs.

Drafting

Red Sox: For the current regime of Dave Dombrowski and Cora, there isn’t a large track record for drafting. However, the two notable picks that Dombrowski made in Jay Groome and Tristan Casas were essentially no-brainer picks for the Red Sox considering where they were in the draft.

Most of the good picks the Red Sox made in the past that paved the way for the team we see today were made by Ben Cherington and Mike Hazen, so Dombrowski doesn’t get credit for them. C+

Patriots: Belichick and Nick Caserio have mastered the art of trading back. They pick up all sorts of picks by trading back several slots, which bolsters their trade assets. Belichick has often whiffed on high picks that aren’t linemen, but he is a genius at stealing late round picks and making them key contributors on Super Bowl-winning teams. B+

Boston Celtics: Early on in his tenure, Danny Ainge was awful in drafting. The only notable draft pick worth mentioning was Leon Powe, and that’s only because the Celtics won the title in 2008 and he got in a couple of games.

In recent history, however, the draft has been Ainge’s friend. After the terrible James Young and RJ Hunter draft, the Celtics drafted Marcus Smart, Terry Rozier, Jaylen Brown and Jayson Tatum. Kudos to Ainge for turning his draft rep around, but his first years drop his grade down a bit. B

Boston Bruins: The case against Don Sweeney is the same case against Dombrowski—his predecessor made the best picks that affect the current team. After all, Peter Chiarelli drafted David Pastrnak, Ryan Donato, Danton Heinen and Anders Bjork all in the same draft.

Sweeney gets high marks for drafting Charlie McAvoy and Jake DeBrusk as well as finding solid players in Brandon Carlo and Jakob Forsbacka-Karlsson. He needs more picks like that in order to raise his grade however. C+

Coaching

Red Sox: How does Cora follow-up back to back division titles? By leading a Red Sox squad that is on pace to have the fourth most wins in MLB history.

While Rafael Devers has seemingly taken a step back in his development, the biggest impact Cora has had on the team is the philosophy. The Red Sox are more aggressive at the plate and more accountable in the locker room, and it is helping them have an all-time season. B+

Patriots: Belichick is lapping the coaching field in the NFL by leaps and bounds, and it especially shows in coaching. His ‘in-game adjustments’ are legendary by this point, and if you drive around New England during football season you can’t go two blocks without some sort of flag or banner proclaiming ‘Do Your Job.’ A

Celtics: Brad Stevens is the Belichick of the NBA. He is the best in the Association at getting the best out of marginal parts. He has earned a reputation in his short stint as an NBA coach because of his work with guys like Marcus Smart and Isaiah Thomas. With stars, there is no limit to the success Stevens can have. A

Bruins: Like the Red Sox and Cora, Bruce Cassidy inserted a breath of fresh air into the Bruins. His quick, offensive styled game brought the Bruins out of the doldrums and lead them to an unprecedented 112 points following a return to the playoffs the previous year.

The difference between them and the Sox, however, is that Cassidy was the one to also develop players like Pastrnak in the Bruins’ AHL affiliate in Providence, so he gets extra marks for that. A-

Free Agency

Red Sox: The biggest blemish on Dombrowski’s record is obviously the David Price signing. He will almost assuredly opt-in over the summer, costing the Sox over 30 million a year for the next four years after this one. The J.D. Martinez signing is a great addition and although Price has been a solid pitcher, the gross overpaying for an ‘ace’ who hasn’t won a playoff start yet cannot be ignored. C

Patriots: The Patriots have been notoriously tight with the purse strings, not willing to pay a cent over what they believe a player is owed. The method they have of letting their stars test the market before deciding what they want to pay them is a good idea, however. Overall, the Patriots get more from late round draft picks and another way than free agents, but they aren’t awful. B-

Celtics: Once again, what have you done for me lately Danny Ainge? Before 2016, Boston was about as far away from a free agent destination as there was in the league. Now? Al Horford and Gordon Hayward have signed max deals to come to Boston, creating a powerhouse in the Eastern Conference. B+

Bruins: The Bruins worst contract in the Don Sweeney era is no doubt the David Backes. contract. The resigning of Brad Marchand and Pastrnak, however, more than make up for that. Add to that the great finds of depth players like Tim Schaller and Brian Gionta, as well as bringing back Anton Khudobin for the 2017-18 season, and Sweeney has done some good work in free agency. B

Trading

Red Sox: This is the major thorn in the side of the Red Sox at this moment. When Dombrowski took over, the farm system was flush with young talent at every position. Then ‘Trader Dave’ decided to take over and upgrade the major league team.

He does get high marks for the players he acquired, namely Craig Kimbrel and Chris Sale. However, he did give up high quantities of prospects to get the deals done, and now the Red Sox farm system is barren.

Dombrowski has managed to find under the radar relievers two years in a row with Brad Ziegler and Addison Reed, but the Red Sox don’t have the prospects this year to go out and trade for a big name. They have no bullets left to fire while teams like the Astros, Yankees, and Indians have prospects aplenty and are still very good.

The Red Sox are behind the rest of the American League in terms of being able to trade for the missing piece they covet. Dombrowski has had this reputation for previous teams he has worked for as well. Gut the farm system and make the team go into full rebuild mode. So for that… C-

Patriots: This is the other aforementioned area where Belichick and Caserio are so good. Look at some of the trades that have been successful for the Patriots. Guys like Kyle Van Noy, Martellus Bennett, Danny Amendola and Randy Moss all arrived via trade. The Patriots trade high draft picks lower ones in exchange for solid players like Malcolm Mitchell and Joe Thuney.

Trading for often overlooked, solid foundational players is what the Patriots dynasty is built on. Some trades have busted, like Albert Haynesworth and Chad Johnson but overall, Belichick is light years ahead of the rest of the league. However, recent the recent trade of Jimmy Garoppolo has the Patriots reign on the brink of destruction, so that brings him down. B+

Celtics: Where to start with trader Danny. He single-handedly turned the Celtics franchise around in the summer of 2007 when he acquired Ray Allen and Kevin Garnett in two blockbuster deals that brought the 17th banner to the Garden rafters. But they thought it was done.

Nope, Ainge flipped Garnett, Paul Pierce, and Jason Terry to the Nets for a bevy of first-rounders over the next few years. Ainge swiped a 5-foot-9 guard named Isaiah Thomas who was a no name at that point and used him to attract the free agents he needed to rebuild the Celtics.

He even goaded another first rounder out of general manager Bryan Colangelo in Philadelphia because he knew he wanted Jayson Tatum. Ainge is the modern-day Red Auerbach. If a rival general manager sees the name Ainge calling, he better hang up quickly. A+

Bruins: The Bruins have made several noteworthy trades underneath Don Sweeney’s leadership. They acquired Drew Stafford and Rick Nash in separate deals as well as adding depth in the forms of Nick Holden and Tommy Wingels. While there isn’t a large sample size, I believe that the Rick Nash trade was a good one, and Sweeney has done well to work out of the mess that Chiarelli left him with. B

Overall, I think the Celtics have the best general manager-coach tandem in Boston, closely followed by the Patriots. The fact that Ainge has never lost a trade and has steadily trended upwards in drafting the past couple of years speaks volumes about his ability to adapt.

He has almost single-handedly built the Celtics up from the ground twice, with only a single year of rebuilding in between. Belichick has the pedigree as well, but too many questionable moves have happened recently and too many bad drafts to give him the top slot.

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