How much grief to inflict on President Trump? That is the question currently obsessing Capitol Hill Democrats. 

There is little Democrats can do, on their own, against what they see as the slings of Trump’s manically dysfunctional White House, and the arrows of ultra-conservative Republican lawmakers. 

Ultimately, it will be up to Republican leaders in Congress to exert themselves—as some began to inch toward, late last week, in calls for investigation into contacts between Trump associates and Russian agents during the campaign. 

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If Democrats take the path of loud, aggressive resistance, they risk exacerbating the partisan divide, making it politically harder for concerned Republicans to cross their Trump-loving party base—and, perhaps, harder for Democrats to court moderate voters in the 2018 mid-term elections. Or, perhaps acting reasonable compromising would depress the Democratic base, while letting Republicans act recklessly without consequences. 

From what I hear, last week’s House Democratic retreat made little progress toward reaching a consensus on how to move forward. But it’s increasingly clear that some individual Senators and Representatives are going to take it upon themselves to oppose the White House fiercely. It is also clear that some of the biggest pains in the collective Trump/GOP posterior will hail from the Commonwealth of Massachusetts. 

Perhaps that’s because most of the Massachusetts delegation stands a better chance of reelection than most of their colleagues. Or, maybe there’s something about the Bay State, that breeds a willingness to speak and act out against perceived wrongs. A moral rectitude tracing from the Puritans, perhaps, or maybe an intellectual arrogance rooted in the state’s close association with colleges and universities.  

For whatever reason, New England, and Massachusetts in particular, has a long history of exceptional political trolling, to use the modern social media term, in opposition to their national government. What else would you call the Boston Tea Party?  

There was John Quincy Adams, who even after his Presidency made a nuisance of himself as a Congressman, flaunting a gag rule to speak out against slavery in 1836. Daniel Webster, as Senator, used his famous oratorical skills to be a thorn in the side of Trump’s favorite predecessor, Andrew Jackson. Charles Sumner’s five-hour “Crime Against Kansas” speech on the Senate floor in 1856 was so successfully provocative against slaveholders, he was beaten with a cane for it. Henry Cabot Lodge, as chair of the Senate Foreign Relations Committee in 1919, made it his mission to prevent the United States from entering the League of Nations. It’s fashionable these days to speak of Tip O’Neill’s willingness to break bread cordially with Ronald Reagan, but that shouldn’t obscure the brutal battles the Speaker from Cambridge led against the President.   

Against the current threats, Senator Elizabeth Warren is surely the best-known and most effective counterinsurgent in the Massachusetts delegation, if not the entire Congress. That status, if not already obvious, was confirmed recently when Senate Republicans removed her from the floor debate over confirming Attorney General Jeff Sessions. 

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Warren is now slyly using speculation of a 2020 Presidential bid to bolster her anti-Trump campaign.   

But others in the delegation are making aggressive moves too. That includes Senator Ed Markey—who, at this writing, is heading to the Mexican border to nag Trump over immigration and trade issues. Markey doesn’t have the star power of Warren, but he’s honed his trolling skills for decades. Markey and Connecticut’s Chris Murphy called for investigations into Mike Flynn earlier this month, contributing to the pressure leading up to Flynn’s resignation as National Security Advisor four days later. He has been consistently among the first to publicly condemn Trump’s actions, and was picked to give the weekly Democratic address in response to Trump’s nomination of Neil Gorsuch to the Supreme Court. 

Over on the House side, it’s no surprise that Katherine Clark of Melrose—who led last year’s troublemaking sit-in over gun legislation—is eager to pester Trump. She has introduced a bill to force the President to resolve potential financial conflicts of interest; just this past Friday she sent letters to the FBI, the Secret Service, and the Department of Labor asking what they are doing to ensure security at the Mar-A-Lago country club, after Trump was seen discussing North Korea’s missile launch in front of club members and guests. 

Seth Moulton of Salem has shown little hesitation calling out Trump, quickly becoming a national media go-to for criticism of the President. Worcester Congressman Jim McGovern is, once again, leading an effort to pass an Authorization for the Use of Military Force (AUMF) governing U.S. military involvement in the Middle East. A longstanding fight of McGovern’s, the AUMF push may have new momentum following reports that Trump is considering sending troops into Syria. 

Stephen Lynch of South Boston, who has targeted much of his criticism at Trump’s government hiring freeze, seems to be itching to make noise from his seat on the House Oversight Committee—where Republican chairman Jason Chaffetz is resisting pressure to investigate Russian interference in the 2016 election. In the face of Chaffetz’s obstinance at a hearing earlier this month, Lynch reportedly shouted that “that’s our work… we ought to do it publicly, about the damage done to the confidence in our electoral system. That’s what’s important here.” 

And there’s another worth watching, who might surprise a lot of Bay Staters who rarely pay much attention to the far western regions of the state. Richard Neal of Springfield, a veteran typically more likely to be explaining spreadsheets and parliamentary procedure than delivering ideological diatribes, has been elevated to ranking member of the House Ways & Means Committee. That puts Neal right at the table—as he has literally been, in recent White House meetings—on major tax reform and trade policy issues. 

Neal has already demonstrated a willingness to go for Trump’s jugular. Not only is he making more media appearances outside of his usual 413 comfort zone, he’s also been vowing to take the argument against Republican tax cuts to the public, in hopes of turning popular opinion against their plan. 

Neal’s opposition to Trump is direct and clear cut. Last week, Neal introduced a bill that would require Presidents to disclose any financial interests potentially affected by changes in trade policy. Though not naming Trump, that’s obviously aimed at his undisclosed tax returns. 

And, though not coming directly from Neal, it’s likely he approved an amendment forced to a Ways & Means Committee vote, to obtain Trump’s tax return from the IRS. Ways & Means is one of three House committees with the legal power to look at tax returns. Neal voted in favor of the amendment, which was defeated on a straight party-line vote. 

Neal, the dean of the delegation, with an important post and a reputation for moderation, just might be in the best position to be the Trump era’s breakout opposition leader, if he wants to. If you’re hoping Massachusetts produces another historic political pain in the ass, I suggest you keep an eye on Richie Neal.