Questionnaire: Chicago Sun-Times
As part of the campaign, the Chicago Sun-Times sent out a questionnaire for use in a voter guide they’ll put out. Below are the substantive questions and my answers.
This is… not great Substack content. But, I want a record of these things here.
Grocery prices and inflation in general remain worrisomely high for most Americans. Please describe three steps that the U.S. should carry out to improve the economic outlook for Americans, both short-term and long-term.
Building an economy for all Americans is a central problem of government. My perspective below is grounded in my time working as a public school teacher, as a federal antitrust prosecutor, and as a senior leader in product and business strategy at Microsoft.
1: Invest in growth and innovation
Improving the economic outlook for ordinary Americans depends first on a strong and growing American economy. The first set of things we can do to ensure growth is straightforward: undo the disastrous policies of the last year. End destructive trade barriers, attacks on universities, restrictions on high-skilled immigration, unnecessary conflicts with allies, crony capitalism, and more, so we can promote an open and competitive economy. That’s the path to economic opportunity and lower costs. From there, we can go further: expanded investment in basic research, innovative approaches to regulating emerging technologies like AI that get the safety/speed balance right, on-shoring critical industries, and more.
2: Overhaul skilling and education
Next, we need to make sure that Americans have the opportunity to take advantage of the opportunity created by growth; affordability starts with how much Americans earn. A critical step there is changing the way we prepare Americans for the job market. More and more high-earning jobs with growth potential are projected to require bachelors degrees, but these are out of reach for many. Free college and debt relief can help, but don’t go deep enough. There are higher-ed programs that are faster, more flexible, and cheaper, and are designed to build skills employers want and place people in real jobs. We should invest in expanding the scope of these programs so people can get the skills they need, multiple times in their careers if necessary, and employers can have talent ready on day one. One way to do it is providing incentives for employers to hire through these programs.
3: Expand the care we provide
As we build a strong economy and the skills to let every American contribute, we should also expand the care that Americans have access to. We should finish the work of providing healthcare to all with a public option, and move on to childcare, elder care, mental healthcare, and more. Expansive care will improve quality of life for all Americans and economic competitiveness for the nation. This won’t be done within a few years, but we can make the ambition clear and begin working toward it.
There have been major concerns in Chicago and surrounding suburbs about how the Trump administration has implemented its Operation Midway Blitz campaign. What is your view of the campaign and its execution, and what legislation would you pursue to get at the concerns you have about the ongoing operation?
Midway Blitz, and campaigns like it around the country, are abhorrent and a violation of American law and values. As someone who has worked in federal law enforcement, I believe it must be fair, professional, and above all accountable. Midway Blitz is none of these. It tears apart communities, makes individuals live in fear, and destroys the relationship between citizens and the government—and in doing so, makes everyone less safe.
I support legislation that:
Disbands ICE and shifts its duties to other agencies. This organization and its reputation in American communities is beyond repair.
Shifts the focus of immigration enforcement away from American communities and to borders and points of entry, and away from nonviolent individuals and toward violent individuals and organizations.
Sets standards for recruiting, training, and accountability in immigration enforcement.
However, I know that cruel and arbitrary immigration enforcement is core to the Trump presidency, and I do not expect any of this legislation to pass while he is in office. We can and must propose it to show Americans the direction we want to take, but we can’t lose focus on building a party that can defeat Republicans and take back the White House in 2028. That’s how we will keep our communities safe.
For the foreseeable future, a long-term foreign policy challenge for the U.S. will be China. What is your assessment of the Trump administration’s policy toward China, particularly with respect to the imposition of tariffs and China’s policy toward Taiwan, and what U.S. policy changes toward China would you advocate?
The Trump Administration’s policy toward China has been foolish and feckless. In dealing directly with China, Trump has started and then folded an unnecessary trade war, demonstrating which side has greater resolve. More broadly, China has been working for decades to consolidate influence around the world and pave the way for an international order more favorable to the interests and values of its governing elite. By pulling out of international commitments, ending foreign aid, and antagonizing allies, the Trump Administration is pushing nations toward China and weakening America’s global position. I want the twenty-first century to be a new American century, but Trump seems committed to handing it to China.
I would advocate for:
Reduction in direct tensions with China where possible. These don’t currently serve any purpose for Americans. As someone who worked in a global company, I know that disturbances in the trade relationship and the closing off of the Chinese market to America will only create real economic pain in America.
Aggressive work to re-establish American influence around the world. We must recommit to and expand alliances and aid to preserve and promote a rules-based international order that makes democracy and territorial sovereignty possible.
Ongoing support for Taiwan. Taiwan’s people must be allowed to enjoy the democracy and freedom they have earned over generations, both for their own sake and as a show of commitment to democracy around the world.
There is increasing concern across the country about the erosion of democratic institutions, from the weaponization of the Justice Department for the pursuit of political enemies to mid-census redistricting to skew Congressional seats toward one party’s favor. How concerned are you about these threats, and what do you believe should be done to firewall the country from those threats?
I am deeply, deeply concerned. As a former Justice Department attorney, I understand that the rule of law and the insulation of institutions from political influence are both essential and fragile. These are existential threats to American democracy, and I left my career to join this race because they are so dire. Sadly, I don’t believe most Democrats, including leading candidates in this race, grasp that. We’ve adopted the rhetoric of fighting authoritarianism, but still propose legislative fixes that have no chance of succeeding, or call for “fighting” without completing the thought of how it will make any difference.
The bracing truth is that there is no institutional firewall against them. As we’ve seen over the last year, the President is not bound by regulation, statute, or judicial order. You can’t use law to constrain an outlaw administration; that would amount to passing a law banning breaking the law. Congress and the Supreme Court don’t have their own police forces that can compel the president to follow their orders, for good reason.
If we want to avoid these abuses in the future, we have to make it so our voters never elect people like this again. That is much harder and more long-term work, and it’s unsatisfying to people looking for decisive action now. But that’s the fight we are in. Until the large majority of the American people once again see the value of democracy, we—like every nation—will always be at risk of strongman rule. That’s why my campaign is not focused on promises of near-term fixes, but on getting down to the work of building a political majority that can win.
Cutbacks in federal funding have been used as a cudgel by the Trump administration against Chicago and Illinois, aggravating the strain on City Hall and Springfield finances. What if anything do you believe Congress could do to address this kind of action from the federal government?
Over the past year, the Trump Administration has violated all kinds of federal law, but one they did not is simply appropriating funds without a budget, which is why we had the extended shutdown fight. That appears to have been a step too far (though they were looking into ways to spend without appropriation). The leverage we have in Congress, for the moment, is to hold up appropriations, i.e., engage in another shutdown. We can push to make funding of our state a condition of Democratic cooperation. Hopefully, in the midterms we not only win more seats in Congress but put in the kind of Democrats who have the clarity and resolve to stick out the next shutdown battle. That won’t happen if we choose career politicians whose primary goal is getting along with the party and keeping the job.
What is the most important issue in your district, and how would you address it legislatively?
My district, like districts all over America, is suffering in so many ways. We’re struggling with economic worry, we have masked agents in our streets, we are watching the civil rights of our people getting rolled back, our people are losing access to healthcare, and more. There are many issues we face, and the one under all of them is the persistence of MAGA rule. I want to work on addressing these problems and going further to build an expansive, hopeful future for the district and the country, but that can’t happen until we move past this era.
We are not going to pass progressive legislation under the Trump Administration. It will have get through the House, the Senate, and the President’s veto, and then his agencies would have to implement it faithfully, and even after all that, his Supreme Court would have to uphold it. I am tired of false promises from candidates that we can go pass the things we care about now. But: we can propose legislation that shows America what we’re fighting for and what they will get if they put us back in office. In Congress, we should resist and fight however we can, but we should be putting a vision on the table. Current congressional leadership has done none of this and is failing completely.
Sum up why you believe you are the better candidate for this office.
I am not a career politician. That means I am not a product of a political system that rewards adherence to the existing, losing platform. I’m ready to bring new ideas and new leadership to the table.
I have experience that matters. I have worked in education, in law enforcement, in federal regulation, in global business, and in technology. If we want to build a future of opportunity, growth, and expanding care, I have done the work. Remarkably, none of the leading candidates in this race has done any of that. In particular, I would be the only member of Congress to have ever worked on AI products. We will not be ready to take on the task of regulating AI when nobody in the chamber has any relevant experience.
I am focused on the fight that matters. We need to win back the White House in 2028, and we’re not on track to doing that. We need to build a party that can win, big enough to not only take back the office but knock MAGA out for good. That’s why I’m promoting a vision that can do that. In a field of 16 candidates, I am the only—truly, the only—candidate with a clear-eyed view of the challenge we’re facing and a path to doing something about it.
There are candidates in this race that have raised millions of dollars, and I certainly haven’t. But I believe what makes a serious candidate is engagement with the problems facing the country and a plan to address them, not a rolodex built over years in politics or a large follower count. That’s why I’m running, and it’s why I am the best candidate for the office.



