Your Guide to the 21 Elections to Watch on May 16

The city of Philadelphia promotes turnout on its social media (Philadelphia city government/Facebook)

Voters across Pennsylvania and Kentucky, and in some areas of Colorado and Florida, will resolve major questions on Tuesday, May 16. Who will control the Pennsylvania state House? Who will be the next mayor of Philadelphia, Colorado Springs, and Jacksonville? Can a state judge who gave Donald Trump’s “Stop the Steal” efforts one of its brightest legal victories in 2020 score a promotion?

Voters will also decide who wields power over Pennsylvania’s criminal legal system, whether conservatives take over more local school boards, whether the Pittsburgh left continues its gains, and whether an election denier topples a secretary of state.

The page is prepared by Daniel Nichanian. More may be added to our cheat sheet through Election Night. Check back on Election Night as we fill in each result in the second column.

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Pennsylvania’s House District 163 (general election)

This one special election, in a blue-leaning district anchored in Delaware County, will decide nothing less than who controls the state House. To keep it simple, Democrats need Heather Boyd to beat Republican Katie Ford to defend the seat and keep a slim majority in the chamber.

Republicans defend a seat of their own, HD 108, but it is in strongly red territory and has drawn less attention.
Kentucky’s Senate District 28 (general election)

Republicans are clear favorites to retain this vacant seat, which is in conservative territory, though a three-way dynamic in this general election may complicate things.

State executives

Kentucky governor (Dem)

Andy Beshear, the first term governor running for re-election, is expected to easily secure the Democratic nomination against a pair of challengers.
Kentucky governor (GOP)

Republicans select their candidate to likely face Beshear; Trump-endorsed Attorney General Daniel Cameron, former Trump administration official Kelly Craft, and Agriculture Commissioner Ryan Quarles are the frontrunners.
Kentucky secretary of state (GOP)

Kentucky’s Republican Secretary of State, Michael Adams, who has criticized conspiracies around the 2020 election, faces two Republican primary challengers; one is an election denier who is backed by Mike Lindell, the CEO of My Pillow and close Trump ally, the Lexington Herald Leader reports.
Kentucky treasurer (GOP)

A three-way Republican primary will give the winner the upper hand in the open Treasurer’s race in November; contenders are competing over who would best fan the flames of conservatives’ so-called culture wars.
Mark Metcalf


Pennsylvania supreme court (GOP)

A state judge who gave Donald Trump’s “Stop the Steal” efforts one of its brightest legal victories in 2020, Patricia McCullough, is now running for a seat on the state supreme court, as Bolts reports. Her GOP primary opponent Carolyn Carluccio has also amplified false concerns of voter fraud.
Pennsylvania supreme court (Dem)

Democrats will choose their own nominee for the same supreme court race, with Deborah Kunselman and Daniel McCaffrey competing to move to the critical November general election.
Also, Pennsylvanians will choose the Democratic and Republican statewide nominees for openings on the state’s intermediary courts, the Superior Court and the Commonwealth Court, as well as for county-level seats on local benches like the courts of common pleas.

School Board

PA | South Side Area School Board (Beaver County)
A slate backed by the local chapter of Moms for Liberty, the conservative group targeting school boards nationwide, is running for the local board, critical of local policies like respecting students’ preferred pronouns.
PA | Carlisle Area School Board (Cumberland County)Strongly opposing slates have sprung up here as well, with one group echoing conservative themes such as wanting to remove books from school libraries and earning endorsements from the right-wing Take Back Our Schools organization.
PA | Norwin School Board (Westmoreland and Allegheny counties)Here too, a slate of candidates is campaigning by raising fears about critical race theory or LGBT rights.
Also, The Pittsburgh Post-Gazette reports on the statewide battle between conservative groups and their critics over local school boards; these are also seeing the involvement of the right-wing Moms for Liberties or Take Back Our Schools, for instance in the Camp Hill or South Middleton districts.

Note: Many of these candidates are simultaneously running in both parties’ primaries, so it is uncertain if the contests will be resolved on Tuesday or move on to November.


CO | Colorado Springs mayor

Could Colorado Springs—the military town, home of the right-wing Christian group Focus on the Family and the state’s most populous Republican stronghold—move away from the GOP? Wayne Williams, the former Republican secretary of state, faces businessman Yemi Mobolade, who has positioned himself as a moderate independent, in this mayoral runoff.
Mobolade (Indy flip from GOP)
FL | Jacksonville mayor

Jacksonville is presently the nation’s most populous city with a GOP mayor. In a low-turnout runoff, Democrats hope to flip the mayor’s seat via Donna Deegan, who faces Daniel Davis, a Republican. Davis has attacked Deegan on crime and over her presence at a Black Lives Matter rally that had also been attended by GOP officials.
Deegan (Dem flip)
PA | Philadelphia mayor

A crowded field is vying to be the next mayor of Philadelphia in a wide open Democratic primary that features various ideological factions. Progressives have rallied around Helen Gym; Rebecca Rhynhart has support from more establishment-oriented liberals and The Inquirer‘s editorial board; former city councilmember Cherelle Parker drew the support of the outgoing mayor; and other candidates like real estate magnate Allan Domb pledging to step up policing. Read more in Bolts about the election’s ramifications for the overdose crisis.
Also: keep an eye on the unusual mayoral primary in Pennsylvania’s bankrupt Chester.


PA | Allegheny County DA (Dem)

DA Stephen Zappala, who has long clashed with criminal justice reformers over his punitive policies and the vast racial inequalities in arrests and prosecutions in the county, faces a challenge in the Democratic primary from chief public defender Matt Dugan. Areas that bear the brunt of heavier incarceration have opposed Zappala in the past, Bolts reports, but can Dugan break through in the suburbs this year?
Matt Dugan
PA | Monroe County DA (Dem)

This DA race carries high stakes for the parents of Christian Hall, whose hands were raised when police shot him during a mental health crisis, Bolts reported. In the Democratic primary on Tuesday, one candidate is an assistant DA who said it was justified. Another candidate vows to re-open the case.
Mike Mancuso
See also Bolts’ database of all DA elections taking place in Pennsylvania this year, and our statewide primer of all you should watch – and of the great many races that only drew one candidate.

Countywide Offices

PA | Allegheny county executive (Dem)

A crowded primary will decide the Democratic nominee to lead the state’s second-most populous county. Sara Innamorato, a left organizer who is now in the legislature, faces moderate opponents with establishment support, including Pittsburgh Comptroller Michael Lamb and County Treasurer John Weinstein, who has the endorsement of the county party. Read more in Bolts about why the future of youth incarceration hangs in the balance of this election.
PA | Philadelphia sheriff (Dem)

Sheriff Rochelle Bilal faces three challengers in the Democratic primary, but in a state where sheriffs have far less power than elsewhere, the leading contenders for mayor say the office should be outright abolished.

City Councils and County Commissions

PA | Allegheny County commission (Dem)

A Democratic primary for the county’s at-large seat pits Bethany Hallam, a left-wing organizer who won this seat four years ago, against centrist challenger Joanna Doven. Doven has attacked Hallam, who used to be incarcerated and has made criminal justice organizing a staple of her political profile, over past drug use.
PA | Philadelphia city council

Seth Anderson-Oberman, a progressive union organizer, is challenging three-term council member Cindy Bass in the Eighth District, in Northwest Philadelphia, The Inquirer reports.
PA | Montgomery County commission (GOP)

Joe Gale, a GOP county commissioner who voted against certifying the 2020 election three years ago, is up for re-election; two of the three Republicans on the ballot will move on to the general election.
Gale ousted
Also, across 29 other counties in Pennsylvania, there are 41 other candidates running for county commission who feature in Votebeat’s investigation for amplifying the Big Lie and are in competitive races on Tuesday.