I'd say that he's becoming the Harold Stassen of Illinois politics except that Stassen did actually win two elective offices.
Oberweis keeps morphing his image every election cycle.
In 2002, Obie ran for the Senate. During the primary, he compared Catholic Bishops to the Taliban. After losing the primary, he apologized to pro-life groups and claimed he was pro-life all the time.
In 2004, he tried running for the Senate again. This time, he supported constitutional bans on abortion and gay marriage. He also ran ads blaming illegals for everything. The media was quick to blast him. He instantly became the darling of the Right for being the only IL candidate to raise the illegal immigration issue. The media did some investigative reporting and found that Oberweis Dairy hired illegals. Thus, Oberweis fell in the polls.
In 2005, Oberweis ran for Kane County GOP Chair. He lost.
In 2006, Oberweis ran for Governor. He portrayed himself as a successful business man and political outsider. He called himself the true conservative and entitled to the nomination. IL GOP primary felt differently and rejected him.
In 2008, Oberweis ran for Hastert’s seat. He got Hastert’s backing. Oberweis spent $3 million of his own money to blast Lauzen. When the primary ended, Oberweis ran out of money and begged the NRCC to spend $2 million in the general election. He lost due to people getting tired of slash and burn campaign style. After losing in Nov 08, he finally got the hint and said he’s done with politics.
He won two separate offices, that of County Attorney (at only 23 !) for 8 years, and then the MN Governorship three times (1938, 1940 & 1942) and resigned early in 1943. So that was either 5 or 7 successful general election wins (I don’t know if County Attorney was for 2 or 4 year terms, MN still had 2 year terms for Governor then).
He relocated to Pennsylvania and was still regarded as a fairly serious candidate. He ran for the 1958 Gubernatorial nomination there, placing second (had he gotten the nod, he might very well have won the general as his opponent only lost by less than 2% to George Leader. That would’ve been a first in the 20th century of a man winning the Governorship in two separate states). He was given the 1959 Philadelphia GOP nod for Mayor, but lost 2-to-1. His forays were less serious after that. But I don’t believe Stassen ever flipped his politics to suit an audience (as Oberweis has). Stassen was always a liberal Republican.