Sandy Pensler, a wealthy Republican businessman running in the primary to be Michigan’s next senator, delivered what he thought was a straightforward message in a March television advertisement.
“You’ve seen the invasion at our southern border,” Pensler, 67, said in the ad. “It’s worse than you think. Sleepy Joe [Biden] is using our tax dollars to give cash cards to illegals and to people who can work, but won’t. You work hard, pay your taxes, play by the rules. But our government gives out cash cards to those who don’t. Not on my watch. I’m Sandy Pensler. It’s time to take our country back. I approve this message.”
But Pensler, who has self-funded his 2024 campaign with a more than $1 million loan, appears to have a liability that other GOP primary candidates may seek to exploit. While he praised those who pay their taxes in that ad, a Washington Examiner review of government records found Pensler and his companies have been late on fulfilling thousands of dollars combined in tax bills and faced liens from state agencies and the IRS.
It’s the sort of baggage that could throw a wrench into Pensler’s campaign, which did not return requests for comment. Michigan has a crowded Republican primary, though the Senate race looks increasingly headed toward a general election matchup between former Republican Rep. Mike Rogers and current Rep. Elissa Slotkin (D-MI). Former President Donald Trump last week endorsed Rogers, the preferred candidate of the National Republican Senatorial Committee.
Still, many in Trump’s orbit think Rogers would lose the general election and are also convinced he would diverge from the former president on policy, two longtime Trump allies and GOP operatives told the Washington Examiner. Sen. Rand Paul (R-KY) isn’t fond of the endorsement and said on social media last week that Rogers “is a never Trumper, and a card carrying member of the spy state that seeks to destroy Trump.” Rogers, as the prior chairman of the House Intelligence Committee, notably supported expanding the Foreign Intelligence Surveillance Act — of which Paul is a vocal critic.
“Mike Rogers is a mouthpiece for the Deep State and if he wins in November, which is unlikely, he will immediately stick a shank in President Trump’s back the first chance he gets,” said one Trump ally, who was granted anonymity to speak freely and is not directly involved in the Michigan Senate race. “Pretty much everyone thinks it’s the worst endorsement he’s made this cycle.”
The Michigan Senate primary also includes the likes of former GOP Reps. Justin Amash and Peter Meijer, as well as physician Sherry O’Donnell. Pensler’s spending on his own campaign has helped keep him competitive in the crowded primary. While, for instance, Meijer may have more name recognition in the state than Pensler, the ex-lawmaker raised roughly $500,000 in 2023 to the businessman’s $1 million campaign loan in December of last year.
As owner of the private investment group Pensler Capital in Greater Detroit, it hasn’t been all smooth sailing for Sandy Pensler.
His firm, which says on its website to have worked on transactions totaling more than $35 billion in value, saw its investment into historic manufacturer Denman Tire sour in 2010. That year, Denman Tire, of which Pensler was CEO, filed for Chapter 7 bankruptcy. The filing in Ohio listed Pensler Capital as a 76.5% equity security holder.
One year later, in 2011, the IRS filed a federal tax lien in Trumbull County, Ohio, to recover more than $9,000 that Denman Tire failed to pay from 2009, records show. A county employee told the Washington Examiner the tax lien has still not been satisfied.
Meanwhile, in September 2023, just three months before Pensler announced his Senate campaign, the Illinois Department of Revenue released a tax lien for $148.71 personally issued against Pensler in 2018, documents show. The lien for the since-paid taxes listed Pensler’s lavish Princeton, New Jersey, estate on 3 acres previously owned by William Penn that is now worth roughly $6 million.
And as far as Pensler Capital itself, the company has seen its own problems filing taxes on time.
In 2009, the State of Michigan filed a tax lien against Pensler Capital for $337 in unpaid taxes. The lien wasn’t released until 2014, according to public records.
Pensler Capital faced a tax lien in 2006 from the New York City Department of Finance for $224 in unpaid taxes, public records show. It was released one year later — in 2007.
The New York City Department of Finance also issued a lien against Pensler Capital in 2003, which was released later that year, to obtain a mere $106 from the organization.
To veteran Michigan Republican campaign strategist Fred Wszolek, Pensler’s tax problems will only throw more cold water on his uphill 2024 bid.
“His children need to stage an intervention before he squanders more of their inheritance,” Wszolek told the Washington Examiner. “Rogers is now going to run the table.”
Kyle Kondik, managing editor of the University of Virginia’s nonpartisan Sabato’s Crystal Ball political analysis newsletter, said tax problems for candidates are not necessarily unusual.
However, they are ripe for public scrutiny and will likely be seized on by opposing candidates, according to Kondik.
“People who have been elected tend to be more vetted,” Kondik said.
It’s not the first time Pensler has run for federal office.
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Pensler lost in the 2018 GOP Senate primary in Michigan to John James, who lost the general election contest for the Senate seat that year but went on to score a House seat in 2022. Pensler spent $5 million of his fortune on that primary race, according to Federal Election Commission filings. The race was ultimately won by incumbent Sen. Debbie Stabenow (D-MI), whose retirement announcement sparked the race in which Pensler, Rogers, and Slotkin are now competing.
Pensler also unsuccessfully ran for a House seat in 1992.
“The American experiment is in big trouble,” Pensler said in a campaign video announcing his 2024 Senate bid. “It’s burning. I believe we can turn it around but we need to apply basic morals, take responsibility, and fight like hell.”