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At one event in New Hampshire the fall of 1995, he told Gov. Steve Merrill I was the fastest driver he’d ever seen. Then, in a flash of his famous dark wit, he pointed at me and deadpanned to Merrill that one of the state troopers standing nearby should put me in jail.

I managed to give law enforcement the slip that day, but Dole playfully harangued me about my driving for months. Just before the South Carolina primary, he made a mock announcement about a Cabinet pick.

“I have you in mind for the Department of Transportation, but I’ve taken you off the list,” the Kansas senator said. “You’d make it in 30 minutes to D.C. … I wouldn’t want to ride with him.”

As the countless obituaries recalled this weekend, Dole ascended to the highest rungs of American politics while becoming a skilled public servant who could reach across the aisle. Despite his decades-old reputation as a “hatchet man,” by the time he reached his 70s and was running in his final presidential race, Dole had mellowed. Reporters following his every move saw his sharp sense of humor on display again and again. But connecting with the public was a different story. From the start, it was clear that it just wasn’t his moment.

If I had to pick one word to sum up Dole’s 1996 campaign, it would be: star-crossed.

Indeed, Dole’s obsession with transportation was perhaps understandable because that year he never seemed to be able to get where he was going. I recall groggily rolling over in various Iowa hotel beds — after a harrowing night of winter travel — only to find a campaign staffer on the other end of the phone telling me the senator was stuck in Washington and wouldn’t be coming.

A flurry of snow and ice storms socked the Hawkeye state that year but that was only half of Dole’s problem: the other half was, well, House Speaker Newt Gingrich. In a hint of the extreme partisanship that has come to define national politics for the past two decades, Gingrich and Republican firebrands in the House engineered a series of stand-offs with President Bill Clinton over the budget — that also did damage to Dole.

The impasses led to two government shutdowns lasting a total of 26 days. They were an image problem for Dole, who was trying to appeal to both moderates and conservatives in the GOP, as well as a practical one. The shutdowns effectively froze his campaign at the height of the primary contest. Some of his events in Iowa were canceled and rescheduled three times. More than once he had to call in to a crowd from a plane or a hangar in another city, apologizing for his absence.

Dole eked out a win in the Iowa caucuses, but Pat Buchanan nipped at his heels. The result, with Dole at 26 percent and the populist-conservative former Nixon aide at 23 percent, gave the senator the kind of victory that pundits invariably convert into a loss.

That sort of bad luck continued through the general election. Dole’s campaign often arranged folksy events at businesses or farms to stress how President Clinton’s policies were damaging the economy. I recall one such event where just as Dole was about to walk out, my SkyPager — then de rigueur for the D.C. reporter set — buzzed to advise that consumer confidence had hit some sort of record.

Sometimes it seemed the fates were truly conspiring against Dole. Such was the case in Chico, Calif. when the candidate, then 73, leaned against a railing on a campaign stage and tumbled off when the unsecured decoration gave way.

Because the episode happened during the warm-up speeches, many reporters in a filing center were entirely unaware of Dole’s abrupt exit from the stage. But I happened to be on the camera platform and saw him essentially disappear.

Dole always looked a bit frail from his World War II injuries, including the damage that left his right arm essentially useless, and many of us feared the worst.

But he was quickly back on his feet.

“I think I just earned my third Purple Heart going over the rail. I guess you could say I took a spill for Chico,” Dole said. “I just went over the top.”

Though Dole’s trademark wit was clearly intact, one of his eyes was bloodied by the fall. Clearly fearful of the publicity, Dole was never taken to the hospital. Instead, we flew on to Las Vegas where a casino doctor took a look at the candidate. I distinctly remember being summoned to a hotel suite late that night to be assured by an ophthalmologist that the eye hemorrhage was nothing to worry about and that Dole would be just fine.

While Dole’s aides insisted the episode was nothing to worry about, the candidate — as usual — was more candid.

“It’s a wonder I didn’t get hurt there,” Dole said.

Dole was a what-you-see-is-what-you-get figure. No filter. The real only exception I ever detected had to do with his lingering war wounds. He was stoic about them in public and on camera — but in private, I sometimes saw him grimace in pain as an aide helped him on with a suit jacket or at the simple task of getting in and out of a car.

During the 1996 campaign Dole, his wife, his aides and his surrogates talked ad nauseam about his roots in Russell, Kan. With good reason: one of the biggest burdens Dole bore that year was that he was indisputably a creature of Washington. The same traits and skills that helped win him the post of Senate majority leader often seemed to be a liability during the campaign.

One was a tendency to answer reporters’ questions on the news of the day, even if his campaign advisers were trying to focus on another subject.

Sometimes this happened in the hallways of the Capitol, where campaign aides didn’t accompany him and he was used to offering reporters snappy one-liners. It was these episodes that contributed to his mid-campaign decision to resign from the Senate after 27 years there.

“I will seek the presidency with nothing to fall back on but the judgment of the people and nowhere to go, but the White House or home,” Dole famously said in announcing his plan to quit the Senate.

Of course, “home” wasn’t really Kansas but the iconic Watergate building, where he often emerged during the campaign to greet reporters, toting a cup of coffee from the now-long-gone, Cup’a Cup’a.

Meanwhile detaching himself from the Senate proved to be something less than a complete cure for his verbal indiscretions, which continued to get him in trouble and drive his campaign off message.

Standing on the National Airport tarmac following a swing to New York, Dole weighed in on his campaign’s decision to turn down an invite from the NAACP to speak to the storied Black group’s annual convention. Contradicting aides claiming a scheduling conflict, Dole said he surmised the invite was a political trick.

“I have a flawless civil rights record, and the head of the N.A.A.C. [sic] is a very liberal Democrat, and I think he was trying to set me up,” Dole declared.

As he said it, my mind conjured up a man dumping gasoline on his head and lighting himself ablaze. Dole’s aides also seemed to wince and did their level best to keep him away from the traveling press corps for weeks.

As the campaign wore on, there was more evidence that while it was possible to take the candidate out of Washington it was much more difficult to take Washington out of the candidate. With pundits and pollsters beginning to predict a blowout, Dole insisted his heart was in the race and victory was still possible. But cryptic comments he’d sometimes make in public seemed to suggest he was dutifully completing one last mission rather than making an all-out drive for the White House.

Throughout the campaign, reporters were well aware of a Dole obsession: beating the noise curfew into National Airport, particularly after returning from events out West. He’d occasionally raise the issue in front of audiences, typically in ways that left the crowd baffled.

“It’s a great honor to be here and I know this is on very short notice and we appreciate it,” Dole told a global affairs group in Orange County, Calif. about a week before the election. “We’re going to try to get to Denver yet today, and back into National Airport before 10:20, when they send us to Dulles Airport. But in any event, that’s a small matter.”

It’s tempting to see the self-deprecating Dole — the consummate Washington insider and a proud deal-cutter — as a polar opposite of Donald Trump. But the truth is more complex.

There’s little doubt that Dole saw legislative compromises as his biggest achievements. Asked two years ago about his fondest memories, he touted his work in 1983 with Sen. Patrick Moynihan (D-N.Y.).

“We got credit for rescuing Social Security,” Dole told WPRI-TV. “It was bipartisan and we got it done.”

But there were Trumpian elements to his 1996 race — hints of things to come. Dole never uttered the words “fake news,” but in the contest’s closing days he railed against the press for favoring Clinton and downplaying alleged ethical lapses in his administration.

“When do the American people rise up and say, ‘Forget the media in America?’” Dole thundered to an audience in Houston about two weeks before the election.

“Where’s the outrage in the media? … There’s no outrage. … We will not let these stories be buried on the back pages of section D, C, whatever,” Dole declared in Dallas later that same day. “We’ve got to stop the liberal bias in this country. Don’t read that stuff. Don’t watch television. You make up your mind. Don’t let them make up your mind for you.”

Two decades before Trump reveled in skewering MSNBC as “MSDNC,” Dole blasted the New York Times as “the apologist for President Clinton for the last four years and an arm of the Democratic National Committee.”

Running against the press can quickly turn ugly. I remember one event in Texas where the worked-up crowd responded to the candidate’s anti-press tirade by hooting and jeering at reporters and photographers in their midst, leading some of us to double-check the path to the exit. It was the same kind of concern that became more serious under Trump, when he often riled up audiences by pointing at the camera platform and claiming that the television networks were ignoring him.

Perhaps no one took Dole’s tirades against the press too seriously because, for veteran Washington reporters, there was an air of surrealism about it.

While Dole’s wife Elizabeth often seemed guarded and genuinely wary of the media, the veteran Senate leader appeared downright at ease with us. Perhaps too much so for his sake. He just couldn’t quit us.

While Dole seemed to have a genuine beef with the Times, he was such a gentleman that he had difficulty expressing it to their reporters face to face. As for disliking the rest of the press corps, that was absurd. He reveled in the repartee.

Veteran NBC producer Bobbie Hornig Draper — who died just weeks before Dole — even used the foyer of Dole’s office as a workspace, with his blessing.

In one interview in late 1996, Dole seemed to concede that his broadsides against the press were largely for political effect. “I like the media. They don’t like them in the South,” he told CNN.

Sometimes it seemed that Dole’s grievance wasn’t really with the press, but the public. “I wonder sometimes what people are thinking about — or if people are thinking at all,” he declared in one speech late in the campaign.

In 2016, Dole endorsed Gov. Jeb Bush in the Republican primaries, then shifted to Sen. Marco Rubio, but got behind Trump once he clinched the nomination. Dole also publicly expressed regret that Bush declined to attend the GOP convention that year and for saying he wouldn’t vote for Trump. “I’m really disappointed,” Dole told the Washington Post.

In July of this year, Dole told USA Today, “I’m a Trumper,” though he later added, “I’m sort of Trumped out, though.”

Dole also bequeathed some intellectual and organizational firepower to Trump. The chief of staff to Dole on the Senate Finance Committee, Robert Lighthizer, became U.S. Trade Representative under Trump. At age 93, Dole even showed up to deliver an in-person endorsement at Lighthizer’s confirmation hearing.

A longtime aide to Dole who served as his personal assistant or “body man” — during the 1996 campaign, Michael Glassner, also held a series of top roles for Trump’s campaigns in 2016 and 2020 and continues to have a hand in Trump’s political activities.

Glassner, a Kansas native who was 11 when he started work for Dole, acknowledged some similarities between Dole and Trump.

“They’re both very effective communicators, in their own ways,” Glassner told the Kansas City Star in 2016. “Neither of them are ‘managed’ or ‘handled.’ They do that themselves.”

Maybe Dole’s insidery quality would have doomed him in any presidential race after the one that served as his political swan song, but sometimes I wonder if his barbs and zingers might’ve found more traction in a social-media era. While Dole certainly seemed hopelessly behind the times a quarter-century ago, maybe he was in a curious way ahead of them, too.