Steele might still be back in the state-party trenches had it not been for Ehrlich’s decision to add his name to the Republican ticket in Maryland in 2002. The move almost didn’t happen.
Bob Ehrlich, a self-confessed control freak, shuddered at the prospect of having to worry at every moment during the campaign about what a ticket-mate might be saying. So he gave serious thought to running without one.
The weak Republican bench in Maryland left Ehrlich with few good choices. Eventually, he settled on Steele, an old friend he’d come to know through politics. “It wasn’t a long list,” Ehrlich says, “and we thought we were compatible and so it made sense.”
Ehrlich went on to defeat the heavily favored Democrat, Kathleen Kennedy Townsend, eldest of Robert F. Kennedy’s offspring. As always, the top of the ticket got most of the attention. But Steele—on his way to becoming the highest-ranking black elected official in state history—attracted attention, too. Not all of it was welcome. He got dinged when Democrats challenged his boast that his stepfather had served as RFK’s chauffeur. Steele was forced to acknowledge that he’d embellished the facts. His stepfather, who moonlighted as an airport cabbie, had driven Kennedy exactly once.
As lieutenant governor, Steele was a loyal number two. He headed an education task force that promoted charter schools and a commission designed to get minority-owned businesses more state contracts. He questioned the fairness of the way the state applied the death penalty, suggesting that there had been bias along economic and racial lines. But critics, many of them Democrats, said he had little to show for his efforts.
In 2006, at the urging of President George W. Bush and White House political adviser Karl Rove, Steele sought an open US Senate seat in Maryland, giving up an opportunity to run with Ehrlich for another term. The Senate race was a long shot, but it offered Steele a chance to win public office on his own.
An innovative series of campaign ads featuring the camera-friendly candidate and a cute little dog—produced by the media firm of his top political strategist, Curt Anderson—drew national acclaim. The contest was marred by Democratic overreaching, an illegal effort to plumb Steele’s personal finances. A Democratic Senatorial Campaign Committee researcher who illegally used Steele’s Social Security number to obtain his credit report pleaded guilty to fraud, and a second staffer also resigned.
Like other Republican contenders across the country, Steele was battling strong headwinds. He tried to play down his Bush ties, criticizing the administration for its handling of the Iraq war and Hurricane Katrina. And he described the Republican “R” as a “scarlet letter” in Maryland. But he didn’t back away from his Catholic Church–inspired opposition to all forms of abortion and the death penalty.
On Election Day, he polled one-fourth of the black vote and a majority of the white vote statewide but still lost by 10 percentage points to Ben Cardin.
Passed over for the job of national party chairman when the Bush White House dictated the selection, Steele joined the Fox network’s stable of conservative commentators and became head of GOPAC, which works to elect Republican candidates on the state and local levels.
He also had more time to spend at his Upper Marlboro home. His wife of nearly 25 years, Andrea Derritt Steele, is a Hopkins classmate with a graduate business degree from Wharton who became a Riggs Bank vice president, a job she gave up to raise their two sons, Michael and Drew. They’re active in St. Mary’s Catholic Church in Landover Hills, and Andrea works with Catholic charities. Described as very private and shy, she seldom attends political events.
When Steele announced his candidacy for RNC chairman in late 2008, many wrote him off. He was the outsider on territory that favored candidates who ran from their seats on the national committee. Rove was among those who dismissed Steele’s chances, telling an associate that “it’s just not going to happen.”
However, the little secret about national-party leadership contests is that they’re much more like high-school politics than real elections. Steele hit the road to try to charm the 168 activists around the country who would make the decision. His main assets were the same ones that have served him well over the years: personal warmth, a crushing handshake, and the ability to listen empathetically.
When all was said and done, Steele won with 91 votes, six more than needed.
At a news conference minutes after his win in late January 2009, he couldn’t resist unleashing an audacious boast. Reminded that Obama, campaigning against Steele in 2006, had dismissed him as an amiable fellow with a thin résumé, he responded: “I would say to the new President congratulations. It is going to be an honor to spar with him. And I would follow that up with ‘How do you like me now?’ ”
Asked what he planned to do to change the party’s image, Steele stepped from behind the podium. “I got a nice suit,” he replied. “And the tie is good.”
The six-foot-four clotheshorse says he likes to shop at Nordstrom and buy tailored attire from Kustom Looks in Silver Spring, a favorite of politicians from both parties. Kwab Asamoah, the proprietor, matches 39-inch sleeves to what Steele calls his “7½-foot wingspan.
But as it turned out, snappy duds weren’t enough to keep the new chairman from tripping over his shoelaces.
Steele acknowledges that at times he has a tendency to take things too far. “And I get checked on that, just as when I was a young boy and I pushed the envelope too far and my Mama was there to check me.”
But there’s an edge to his voice when he talks about a double standard that he believes has been applied by his critics, and he posits racism as the cause: “I don’t see stories about the internal operations of the DNC that I see about this operation. Why? Is it because Michael Steele is the chairman, or is it because a black man is chairman?”
Steele’s decision to build his career as a Republican in Prince George’s, the nation’s wealthiest majority-African-American county, has left more than a few scars. He has often heard the term “token black,” and when he chaired the Maryland Republican Party, the white Democratic head of the state Senate called him “the personification of an Uncle Tom.”
Steele still bears a grudge against the Baltimore Sun, which said in a 2002 editorial endorsing Kathleen Kennedy Townsend for governor that Ehrlich’s running mate “brings little to the team but the color of his skin.”
Bob Beckel—who ran Walter Mondale’s 1984 presidential campaign and got to know Steele in the green room at Fox—thinks Steele is “a lot shrewder than people think he is.” Beckel calls him physically intimidating but “also one of the sweetest individuals you’ll ever meet.” Says the Democrat: “He’s done the one thing you need to do in politics. He’s exceeded expectations.”
Steele’s critics, many of them Republicans, claim he’s pursuing a personal agenda at the party’s expense. They point out how he seems eager to put himself on equal footing with Obama. The morning after his election as party chairman, Steele said that the White House had been trying to get in touch with him, presumably so the President could congratulate him on his own path-breaking achievement. The call never came through.