The junior Senator from New Jersey must feel like it’s 2002 all over again as he launches his 2020 run against President Donald J. Trump. Booker has experience opposing circus showman father figures doubling as dastardly overlords. That is, in fact, how he came into political being, as the Newark Central Ward Councilman who 17 years ago had the swashbuckling chutzpah to run against longtime incumbent Mayor Sharpe James.

In the first of his three citywide races, Booker laid the groundwork for victory four years later against a late substitute (Senator Ronald L. Rice) for the evacuating James, who would end up doing prison time on a corruption conviction. As part of that 2002 political christening, the Yale-educated Rhodes Scholar learned strategies for contesting a megalomaniacal incumbent who wields lowest common denominator nativism as his chief method for political survival.

In other words, James v. Booker was the perfect test drive for Booker v. James II, otherwise known as Booker v. Trump.

On the surface, Booker couldn’t strike a more different posture than his rivals.

In his bid to secure a fifth term as mayor of Newark, James used the race card to stave off Booker’s whippersnapper candidacy, a Black version precursor to Trump’s own Asa Earl Carter-lite galvanizing. But if Booker didn’t immediately succeed in wrestling the torch of black urban leadership away from James (he lost 47-53%), he gained more than James did in the win. The latter got packed off to prison and Booker ultimately picked off a U.S. Senate seat.

Alongside the young senator from New Jersey, Trump looks like another power-addled old executive, James-like in his paranoia, crankily past his prime, and always eager to nuzzle his favorite twin security blankets of egotism and ignorance. Booker hopes to sport a transcendent nice guy X-factor, progressive enough to appeal to millennials and sufficiently corporate to land on the national scene with an abundance of cash.

For all their differences, Booker and James were both non-Newark natives who arrived in politics as out-of-towners and fastened themselves to the bowels of New Jersey’s signature parochial city in their separate bids to demonstrate urban intestinal fortitude. Finally, they also both proved engaging and theatrical, perfect foils in the now cult classic documentary movie about the campaign, Street Fight.

In the case of his coming match-up with the sitting Republican President, Booker once again enters the fray with the more polished and prepared profile. But he also offers a sense of showmanship honed from his earliest days as James’ up-and-coming tormentor, for Booker needed to become as animated a public presence as his elder interlocutor in order to chase him off the stage. As other Democrats line up to run in the primary, Booker and his allies can make the case that he is arguably that individual best prepared to go toe-to-toe with the similarly social media-crazed Trump on Twitter. The veteran of his own critically well-received TV show, Brick City, Booker also possesses a telegenic gift that other party rivals lack, which will no doubt prove useful as he tries to gain traction against the former Apprentice star, whose long-gone game show gleam bears dark and deepening legal embroilments reminiscent of James.

Editor’s Note: This piece is reprinted from our 2019 Year in Advance.