Bob Dole accomplished many remarkable things in his long life before dying over the weekend at age 98. But in today’s political climate, winning the Republican presidential nomination while serving as his party’s leader in the Senate looks especially difficult to replicate.

Can you imagine Senate Republican Leader Mitch McConnell (Ky.), who is by most standards more ideologically conservative than Dole, becoming the party’s presidential standard-bearer? Or even winning the hearts and minds of rank-and-file Republicans? The same can be said of just about any other party insider in recent years.

Indeed, Dole’s 1996 presidential campaign may have been the beginning of the end for the Republican establishment. He faced a stronger than expected challenge from populist conservative Pat Buchanan in the early states, even losing the New Hampshire primary to Buchanan. But back then, the establishment was strong enough to circle the wagons around Dole and suppress a conservative insurgency. And even most of the conservative movement, put off by Buchanan’s positions on trade and foreign policy and eager to work in tandem with the mainline GOP, eventually rallied to Dole.

The longtime Kansas senator was a conservative by temperament and had followed the Republican Party along its journey to the right. But he could never quite keep up. Then-candidate George H.W. Bush painted him as a tax-hiker in 1988. And when Dole accepted conservative icon Barry Goldwater’s endorsement in 1996, he quipped, “Barry and I, we’ve sort of become the liberals.” Goldwater agreed.

A more memorable quote from that campaign — which felt like a farewell tour en route to an 8-point defeat at the hands of former President Bill Clinton — was his plea to movement conservatives: “I’m willing to be another Ronald Reagan, if that’s what you want.”

It took the failure of George W. Bush’s presidency and the gracious defeats of John McCain and Mitt Romney to get the conservative base to change its tactics. No longer do these voters follow the old pattern of threatening to back seemingly unelectable alternatives to the establishment only to relent and hand out the Republican nomination like a gold watch at a retirement party. Now they make good on their threats, picking in 2016 someone with a fairly Buchananite platform in Donald Trump.

As his liberal critics on Twitter loved to point out, Dole backed Trump, too, becoming the most important Republican of his generation to do so. Once he represented the alternative to wild card candidates like Trump, but in 2016 and 2020, Dole rejected the old establishment, too.