Retiring Guy's Digest: Wisconsin Democrat trifecta flip #1: Democrat Dan Bukiewicz defeats Republican Dylan Pfaffenbach to flip 21st Assembly District (open seat UPDATE)

Saturday, November 7, 2026

Wisconsin Democrat trifecta flip #1: Democrat Dan Bukiewicz defeats Republican Dylan Pfaffenbach to flip 21st Assembly District (open seat UPDATE)

Wisconsin Democrats needed 5 seats to flip the Assembly. They flipped 8.

After serving 7 terms representing the 21st District, Republican Jesse Rodriguez chose not to run for re-election.

Democrat Dan Bukiewicz, current mayor of Oak Creek, easily defeated 21-year-old Dylan Pfaffenbach, restaurant manager, with an emphatic flip.

Election results: Ballotpedia

Headline: Urban Milwaukee, 11.3.2026

Graham Kilmer reports:

The purple district includes portions of the southern end of the city of Milwaukee surrounding Milwaukee Mitchell International Airport and the city of Oak Creek.
With all in-person votes counted, Bukiewicz won the seat with 59% of the vote. The seat had been held by Republican Jessie Rodriguez since 2013, following a partisan gerrymander in 2011 that entrenched Republican control of the state Legislature. But redistricting recently made the seat highly competitive.
Bukiewicz entered the race for state office with an existing political base, having served as mayor of Oak Creek since 2017. As president of the Milwaukee Building & Construction Trades Council, Bukiewicz also has deep ties to organized labor. The International Union of Operating Engineers Local 420 and the Plumbers Union Local 75 were among the top contributors to his campaign.
But they did not come close to the money spent by the Assembly Democratic Campaign Committee (ADCC), controlled by Minority Leader Greta Neubauer. The ADCC spent $1.2 million in its bid to pick up the critical seat. The Republican Assembly Campaign Committee — among the beneficiaries of enormous political spending by conservative billionaires Richard and Elizabeth Uihlein and Diane Hendricks — provided Pfaffenbach’s campaign with more than $314,000.

The respective vote tallies in the August 11th primaries indicated that the Democrats had the advantage here.

Original 5/8/2026 post, "Wisconsin 2026 elections: Who will run in the 21st Assembly District now that Republican Jesse Rodriguez has retired?" starts here.

The major change to the boundaries of the 21st is shifting South Milwaukee to the 20th and the Milwaukee airport neighborhood from the 20th to the 21st. All of Oak Creek (population 38,797) remains in the district.

Maps and election results: Ballotpedia

Photo and headline: WTMJ, 5/7/2026

Wisconsin state Rep. Jessie Rodriguez (R-Oak Creek) announced Thursday she will not seek reelection this fall, ending nearly 13 years representing the 21st Assembly District.

Rodriguez is the second Republican representing a district that voted for Kamala Harris in 2024 to announce she won't seek reelection. She is also the 12th Assembly member overall to retire or seek another office ahead of 2026. [emphasis added]

Rodriguez cited family as the driving force behind her decision.

Perhaps another reason for Rodriguez's decision is that the 21st is one of the most likely Assembly districts to flip from Republican to Democratic.

Democrats Dan Bukiewicz and Jessica Seawright will face off in an August primary to determine who will run against a Republican candidate in November.

Other Wisconsin 2026 election posts:

1st Assembly District. (6/11/2026)

2nd Assembly District. (6/14/2026)

3rd Assembly District. (6/15/2026)

4th Assembly District. (6/17/2026)

5th Assembly District. (6/18/2026)

6th Assembly District. (6/20/2026)

7th Assembly District. (6/21/2026)

8th Assembly District. (6/21/2026)

9th Assembly District. (6/22/2026)

10th Assembly District. (6/23/2026)

11th Assembly District. (6/23/2026)