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HoosLeft Podcast #144 - Guest: Jessica Bailey for State Comptroller

The two-term Porter County Clerk and candidate for statewide office joins the show to talk about the role of comptroller, how her current gig has prepared her for it, and why electing a Dem matters.

SUMMARY:

After a month’s delay caused by the derecho that knocked out power across Northwest Indiana, Scott Aaron Rogers finally sits down with Jessica Bailey — two-term Porter County Clerk and the Democratic Party’s candidate for Indiana State Comptroller. The conversation is a genuine deep dive into one of the least-understood offices on the statewide ballot: what the comptroller actually does (payroll for every state employee, disbursing billions to schools and counties, managing the state’s HoosierSTART deferred compensation plan, sitting on the State Board of Finance), how incumbent Elise Nieshalla has used the office to wade into culture-war investment fights over China divestment and ESG, the real limitations of the state’s transparency portal, and — drawing on her own experience running elections in Porter County — a clear-eyed, reassuring breakdown of just how difficult it actually is to steal an American election. It closes with a demonstration of Porter County’s homegrown mobile voting unit, one of only two in the state.

Progressive Indiana Network: https://progressiveindiana.net

HoosLeft: https://hoosleft.us

Jessica Bailey: https://baileyforindiana.com/

HoosLeft and PIN rely on your support. To receive new posts and support our work, consider becoming a free or paid subscriber.


WHAT’S INSIDE:

00:00:23 Introduction: Take Two

- Scott explains the month-long scheduling delay: a derecho tore through Northwest Indiana while heavy rain hit central and eastern Indiana, leaving Jessica’s region without power for up to two weeks and knocking her offline too.

- Jessica Bailey: two-term elected Porter County Clerk, now the Democratic nominee for State Comptroller in November.

00:01:22 Support the Show

- HoosLeft and Progressive Indiana Network don’t paywall content — support at progressiveindiana.net ($5/month or $50/year) sustains the project. Social handles: @hoosleft.us on Bluesky, Instagram, and Threads; @HoosLeft on Facebook, TikTok, and YouTube; PIN is @pinindiana on Bluesky and TikTok.

00:02:49 Welcome: Jessica Bailey for State Comptroller, and This Summer’s Long Recovery

- Jessica describes the scale of ongoing recovery: rebuilding roads and utility poles, replacing lost food and groceries, and home repairs that will take months. FEMA is running workshops in Portage this week, drawing in residents from Lake and LaPorte Counties as well — welcome relief given earlier federal cuts, though Scott notes the story has largely fallen out of the news cycle even as recovery continues.

00:05:20 What the County Clerk’s Office Actually Does

- Beyond the visible, “sexy” work of election administration, the clerk’s office handles all court docketing (from marriage licenses to criminal, divorce, estate, and adoption filings), departmental payroll, and managing an influx of over 400 seasonal poll workers per election in Porter County alone. Jessica’s framing: “it’s good when government’s boring” — it means the public is being served quietly and competently.

00:07:20 Why Administration? Fixing a Broken Election Board From the Inside

- Jessica ran for clerk specifically to secure an automatic seat on the county election board after a frustrating experience: while running for school board (she served six years on it before her time as clerk), she filed a complaint against another candidate that her irregularly-scheduled election board sat on for nearly two months — too late to matter before voters had already decided. The board technically followed the 48-hour notice law but gave no advance schedule, meaning residents had to physically check the commissioner’s chambers door to know a meeting was happening.

- As clerk, she fixed this immediately: fixed monthly meetings at the same location, notifications via social media, an app, and the county calendar, in addition to the legally required posted notice.

00:10:39 Auditor, Comptroller, Same Office: A Confusing Rename

- The state constitution still technically calls this office “state auditor,” even though it was renamed comptroller and will appear on this year’s ballot under both names during the transition. Its core functions: paying all state employees, paying vendors, and managing deferred compensation.

00:12:39 State Payroll: Same Job as County Clerk, Much Bigger Scale

- Jessica currently manages payroll for 45 staff plus an influx of 400+ seasonal poll workers twice a year — a fraction of the state’s employee count, but she notes the state’s payroll is relatively stable year-round (unlike her own seasonal spikes) and runs through an automated portal, making the underlying process highly scalable to a much larger workforce.

00:14:33 The State Board of Finance and the Three-Minute Meeting Problem

- The comptroller also sits on the three-member State Board of Finance (comptroller, auditor, and the governor or their appointee), which approves budget transfers and additional appropriations — functionally similar to a county council, which Jessica says rigorously questions every request. By contrast, she describes watching a full year of Board of Finance meetings on YouTube in about 30 minutes: no real discussion, appointees standing in for the actual officials, and votes taken with essentially no public accountability despite overseeing millions of dollars.

00:17:41 Dispersing Billions to Schools and Counties, and When Money Goes Astray

- The legislature sets funding formulas, but the comptroller’s office executes the actual transfers (via ACH, not literal checks) to schools and counties statewide. Jessica describes a real incident at the county level where a misdirected ACH deposit added an unexplained extra million dollars to an account — resolved by contacting the correct recipient office and having the funds withdrawn and redirected, all trackable and auditable by the State Board of Accounts.

00:19:58 Proactive Fixes and Why You Can’t Just Ask to See the System

- Keeping an accurate, updated chart of accounts for each entity reduces human error in fund routing. Jessica notes she can’t simply inspect the state comptroller’s current backend systems from outside — that access requires actually holding the office or working within it, partly for legitimate background-check and security reasons.

00:21:00 Is There a Role for AI in the Comptroller’s Office?

- Jessica is comfortable with AI for polishing communications and creating graphics, but wants a human double-checking anything related to actual money movement or distributions. She’d welcome the State Board of Accounts piloting AI-assisted auditing incrementally, given the office no longer performs the auditing its former name implied.

00:22:43 HoosierSTART: The State’s Deferred Compensation Plan Explained

- Jessica distinguishes three retirement vehicles: deferred compensation (voluntarily delaying pay to a later date), a vested pension based on years of service, and a standard invested 401(k)-style account. HoosierSTART functions essentially as the state’s managed deferred-comp/401(k) equivalent, and the comptroller holds one vote (among several) on its governing board.

00:24:30 Divesting from China: Culture War Meets Investment Policy

- Scott lays out his read: the state legislature mandated INPRS (the pension system) divest from China-related holdings, but that mandate never actually applied to the separate deferred compensation program — incumbent Elise Nieshalla voluntarily aligned the two anyway, a discretionary culture-war-flavored move Jessica confirms wasn’t required.

00:25:57 ESG Investing, Who Controls These Decisions, and the Israel Question

- Nieshalla also pulled deferred-comp investments from companies engaging in ESG practices — a decision Scott and Jessica agree runs counter to research showing ESG-oriented companies often deliver better returns. Jessica notes changing course would require board-level research and, ultimately, a vote — no single official unilaterally controls these calls, since an outside consultant (hired by the deferred compensation board, not the Board of Finance) executes the actual portfolio decisions.

- Scott extends the logic to the state treasurer’s roughly $100 million investment in Israel bonds, given documented war crimes concerns — Jessica’s response: the precedent is already set by the China decision, opening the door to broader conversations about where Hoosier retirement money should and shouldn’t go, evaluated on returns and ethics alike, without singling out any one country.

00:30:10 The Transparency Portal: What’s There, What’s Missing, and Diego Morales’s Real Name

- The portal lists state contracts and employee salaries, but recently had contact information stripped from state employee listings — meaning you can find someone’s salary but have no way to actually reach them at their state email. Jessica also flags a basic usability failure: unlike Indiana’s statewide Odyssey court records system, which supports wildcard name searches, the transparency portal offers no fuzzy search — meaning if you don’t know that Secretary of State Diego Morales’s legal first name is actually “Caesar,” you won’t find his entry at all.

00:34:32 Do We Ever See the Losing Bids? Good Old Boys Club Contracting

- The portal only shows contracts that were ultimately awarded, not competing bids — meaning there’s no way to verify whether the state actually chose the best value. Jessica calls this a great idea worth pursuing. Scott connects this to Governor Braun’s recent elimination of minority- and women-owned business contracting consideration, arguing that without visibility into losing bids, the public can’t tell whether qualified smaller or diverse firms are being passed over for well-connected companies.

00:37:22 What Jessica Is Most Excited to Fix, and Marketing a Portal Nobody Knows Exists

- Jessica’s priorities largely track the gaps already discussed: a more user-friendly, more complete transparency portal, and basic marketing — the office never adequately explained the auditor-to-comptroller rename or promoted the transparency portal’s existence, something she says could be fixed simply by using the office’s existing social media presence and public appearances more deliberately.

00:39:22 Why a Boring Administrative Office Actually Matters

- Asked what a Democrat brings to a technocratic role versus Nieshalla, Jessica reframes the question back on her opponent: if you’re not asking hard questions on these boards and not getting information to taxpayers, why seek the position at all? Scott notes Nieshalla has waded into matters arguably outside the office’s purview (like the Kinsey Institute), suggesting the role may be functioning as a political springboard.

00:41:06 Running Her Own Election as County Clerk: No Champagne on Election Night

- As sitting clerk, Jessica will legally oversee the very election she’s a candidate in — but with a director and assistant director handling day-to-day operations, all ballot-facing work performed with a mandatory bipartisan counterpart, and Jessica’s own pre-set administrative decisions (polling and vote center locations) already finalized before Election Day.

- On election night itself, while everyone else celebrates, Jessica will be verifying flash drive returns, absentee ballot counts, and accounting reconciliation — likely learning her own race’s outcome later than everyone else, since Indiana operates on Eastern time while Porter County runs on Central.

00:43:20 Preparing for Mail-In Voting Restrictions

- Anticipating fewer mail-in ballot requests and more early-voting interest under new federal restrictions, Porter County has extended early voting hours into two evenings a week and expanded its mobile voting unit’s evening availability for people who can’t reach the polls by 6 p.m.

00:45:21 How Porter County Built Its Own Mobile Polling Place

- After a brief on-air cat cameo, Jessica explains Porter County’s VoteMobile — one of only two such units in the state (established around 2020), built from a repurposed senior center bus with a wheelchair lift, seats removed, and added electrical wiring to run voting equipment. It exists because a legislative change now requires host locations to sign responsibility for expensive voting equipment; many community locations (mobile home parks, apartment clubhouses) were happy to host voters but unwilling to take on that liability, so the county built a traveling solution instead of buying an off-the-shelf trailer with no year-round storage space.

00:49:25 Meeting Voters at the Gas Station, and Vote Centers vs. Precincts

- The Vote Mobile will appear at downtown trick-or-treat, a farmer’s market, and two gas stations this cycle — meeting people where they already are. Porter County has also fully moved to a vote center model (rather than fixed precincts), so voters can cast a ballot anywhere in the county convenient to work, home, or routine, including at schools serving as vote centers for out-of-town teachers.

00:51:14 Six Early Voting Locations, Eight Boards

- Porter County runs six early voting locations (with eight total boards, since busier sites run two simultaneously) plus the mobile unit — a significant expansion from the single early voting site and traditional precinct system Scott recalls from his own experience.

00:52:02 Could a Bad-Faith Clerk Actually Steal an Election?

- Asked hypothetically how a bad-faith GOP county clerk elsewhere in the state might attempt to suppress turnout, Jessica declines to call anything strictly impossible, but stresses that Indiana’s bipartisan legal framework — requiring a bipartisan election board for hours, locations, and ballot handling — makes real malfeasance extremely difficult if the rules are actually followed.

00:54:05 Public Accountability and Why Stealing a Statewide Election Is Nearly Impossible

- Every election board meeting is open, public, and recorded — Jessica’s advice to frustrated voters is to actually show up and advocate in person for more locations or hours, since underfunding often stems from councils simply not hearing that demand.

- On a statewide scale, Indiana’s 92 counties each run elections their own way across four different certified vendors, and the only system connected to the internet at all is the e-poll book (which only tracks who has voted, not any vote tabulation) — making a coordinated statewide theft logistically implausible.

00:56:22 Closing: Where to Find Jessica Bailey’s Campaign

- Campaign: baileyforindiana.com, and baileyforindiana on TikTok, Facebook, and Instagram.

00:57:24 Closing and Sign-Off

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