I hate to be the guy to defend him every time, but here I am again. Jeremy Jacobs is a good owner, and dare I say he may be the best owner in professional hockey.
The owner's job isn't to win cups. It's to maintain an efficient business and lead an organization that is profitable with a sustainable balance sheet. He provides the budget to the hockey operations department and it's hockey operations' job to use those resources to put the team on the ice with the goal of winning. And Hockey Ops is accountable to ownership because winning/losing affects the balance sheet, etc. And in the cap world, you can't blame ownership for being cheap anymore.
The characterization of Jacobs as just money grubbing and leeching off the Bruins isn't even true. There have been some NHL owners who were rapacious grifters looking to line their own pockets - Bruce McNall, the Atlanta group, etc. Jacobs by contrast has set up a very healthy organization with a long-term scope. Per Forbes the Bruins are the 5th most valuable franchise in the league, but they're actually in healthier shape than the organizations ahead of them: the Rangers (1) and Leafs' (2) ownership groups are really leveraged. Like, majorly. The Habs (3) are always at the mercy of politics and local economics, and since the last Forbes list came out the Blackhawks (4) have taken massive hits to their value for on and off ice reasons. The Bruins are not leveraged very much at all compared to the rest of the league, they own their own television and arena, just opened a new practice rink and other facilities in the last few years, etc.
In a 32 team league it's hard to win a cup. But the Bruins have consistently been in the hunt for the last 13 years and made it to three finals and got one cup over that span. The idea of an owner going all in with resources or meddling in operations because they treat the franchise like a toy and winning becomes a higher goal than stability like a Jerry Jones type usually causes more trouble than success (look at Jerry Jones' Cowboys). The Rangers, Leafs, and Habs haven't won anything in a long time. But there's some perception that Dolan cares more because he can be a spendthrift, but they usually have a small window where they're competitive for 3 years then out of the playoffs for 5 years, etc. Snyder in Philly was the same, chasing cups and failing for 30 years causing rebuilds every 4 years. At least the Bruins have sustained something.
People mainly hate that JJ didn't open the wallet to spend a lot on free agents back in the 90s when the Red Wings and Rangers were going crazy, etc. and they also blame him for Harry Sinden being too much of a hardass in negotiations. And the things that the Wings, Rangers, Blues, Stars, etc. were doing in the 90s led to a massive work stoppage and threatened the viability of the league.
Not trying to praise the guy and say he's perfect, but he's far too hated now and doesn't get credit for the good organization that he's built here. The Bruins might be the healthiest organization in the league financially right now and that will give hockey operations the resources to be competitive. It's on Neely/Sweeney to turn that into cups.
