County Executive Races Taking Shape

Competitive Races loom in Anne Arundel, Frederick

County Executive races in the eight of the nine counties are beginning to take shape for the 2022 election. All counties with an Executive, except for Cecil County, will be on the ballot next year. Let’s take a look at the races.

Anne Arundel County: Democratic Wealthy Horseman Steuart Pittman is running for re-election, with a crowded field of Republicans lining up to take aim at him.

Pittman himself was accidentally elected by Anne Arundel County voters in 2018: he only defeated incumbent Republican Steve Schuh as a reaction against Donald Trump. Pittman himself was never prepared to lead, and has shown himself repeatedly to be out of touch with county voters and not up to the job to which he was elected.

Two Republicans are already in the race. Former Delegate Herb McMillan formally jumped into the race this week. Chris Jahn announced earlier this year. We interviewed him on The Duckpin Podcast back in March.

County Councilwoman Jessica Haire will be running, and is expected to announce her candidacy very soon. Delegate Sid Saab is also considering jumping into the race, as is packaging executive Marwan Moheyeldien (a story first reported at The Duckpin).

The GOP primary is looking like it will be the most crowded Republican primary since 2006, when then Delegate John Leopold (37%) defeated former Delegate Phil Bissett, Delegate David Boschert, teacher Tom Angelis, and Deputy School Superintendent Greg Nourse.

Baltimore County: Incumbent Democrat Johnny Olszewski, Jr. is running for re-election after announcing that he would not run for Governor.

Republicans are still waiting on a candidate to announce their intentions. While this is a tough race, it’s important for Republicans to put forth a strong candidate in order to help the top of the ticket. In 2018, Insurance Commissioner Al Redmer easily dispatched professional doofus Pat McDonough, but went on to lose the election to Johnny O.

Frederick County: So far, this is where the action is as it relates to County Executive races. With incumbent Democrat Jan Gardner term limited, the Democratic primary is already starting to take shape. Two Democratic members of the County Council, Jessica Fitzwater and Kai Hagen are in, as is former Frederick County Board of Education Daryl Boffman.

On the Republican side, State Senator Michael Hough is the only Republican who has announced his intention to run. It is incumbent for Frederick Republicans to keep their house in order, as Republicans have been plagued by infighting for years between conservative Republicans and the big government statists in the Frederick County Conservative Club. With Democrats gaining a registration edge in the county last year, any infighting that distracts from their Democratic opponents would likely give the election away.

Harford County: Incumbent Barry Glassman is term-limited and running for Comptroller. The Republican primary has attracted two candidates: State Senator Bob Cassilly and former County Council President Billy Boniface. Given the partisan makeup of the county, the Republican primary will ultimately decide the election; Democrats will put up a candidate, but it will be of no consequence.

Howard County: Incumbent Democrat Calvin Ball announced last week that he was running for re-election. That puts all eyes on Republicans to see who their candidate will be. Some believe that former County Executive Allan Kittleman may seek a rematch against Ball. Kittleman, however, is serving a twelve-year term on the Maryland State Worker’s Compensation Commission, a term that does not expire until 2030. It’s hard to imagine that Kittleman would step down from this post to make another run, especially considering his professional expertise as an attorney is in worker’s compensation.

Montgomery County: Incumbent Marc Elrich is by far the most radically left-wing of all the state’s county executives. As usual for Montgomery County, he has already attracted multiple high-level primary challengers. Businessman David Blair is back for a second run; he lost to Elrich in the 2018 Democratic primary by a mere 77 votes out of over 129,000 cast. County Councilman Hans Riemer, who is term-limited, has also entered the primary. This primary will test the mettle of the Montgomery County progressive wing as it faces the “business” wing of the Democrats.

A warm body will run as a Republican and lose.

Prince George’s County: Incumbent Angela Alsobrooks is, surprisingly, running for re-election. Many, myself included, thought Alsobrooks was the front-runner in the Democratic primary for Governor. Considering Republicans haven’t even fielded a candidate for Prince George’s County Executive since Audrey Scott ran in 2002, there will be no unexpected drama here.

Wicomico County: If the Wicomico County Council had any sort of clue, Carl Anderton would already be their County Executive. But the County Council managed to screw it up not once, but twice. Voters will likely correct this error next year, assuming Anderton does in fact run. Democrats will certainly field a competitive candidate; they have been very competitive in these countywide races, including electing Richard Pollitt as the first county executive in 2006 and re-electing him in 2010. Regardless, Anderton remains the overwhelming favorite.