Everyone’s going to be attacking Joe. Photo-Illustration: Intelligencer. Photos: Getty Images

None of the 20 Democratic presidential candidates who’ll debate in Miami over two nights this week (half of them on Wednesday, the other half on Thursday) have ever done anything like this before. Every member of the field — seven senators, one current governor, one ex-governor, five current or former House members, two mayors, one ex–Cabinet member, one former vice-president, one entrepreneur, and one New Age author — takes the stage with different imperatives and incentives. For many of the long shots, this could be their best chance to break through. Meanwhile, most of the favorites could easily play it safe — or they could light it up and go on the attack.

Here, based on conversations with leading campaign strategists, debate veterans, and candidates from across the party, is what each candidate will probably be looking to do, and how he or she might do it.

WEDNESDAY:

Elizabeth Warren

What does she need to do? Warren is on the rise in polling, and neither of her two most obvious rivals — Joe Biden and Bernie Sanders — will be onstage with her. That should make it easy for Warren to do what she’s already been doing: talk with specificity about the progressive policy plans she’s been unveiling to great fanfare, without needing to criticize any other candidate too sharply. This tactic has won her praise as a serious contender, and she’ll be eager to amplify that in front of her biggest national audience yet.

Whom might she attack? Warren has almost no incentive to go after anyone sharing the stage with her — especially considering that her two main competitors will almost certainly be attacking each other the next night.

Who might attack her? Some of the longer-shot candidates like John Delaney or Julián Castro may see attacking Warren as their best bet at making headlines.

Beto O’Rourke

What does he need to do? Remind the primary electorate why so much of it fell in love with him just a few months back. O’Rourke is still a contender, but he’s looking to get his spark back after a few months of slipping in the polls. Allies believe the debates could offer him a great chance at this, since he’s essentially been practicing Q and As nonstop — basically all of his campaign events are town hall style. He’ll be center stage with Warren, which gives him a chance to look like a top-tier candidate again for the night, and he’s almost certainly going to be looking for a viral moment like the ones that helped launch his national profile during his Senate race in 2018. The difficult part is making sure he doesn’t look like he’s planning that, or trying too hard.

Whom might he attack? Seemingly abandoning a personal policy of not going after his rivals, O’Rourke has recently been ratcheting up his criticisms of Biden’s political philosophy. So, like almost everyone else, Biden.

Who might attack him? It’s possible Castro might criticize O’Rourke if he believes Beto’s standing in his way, but O’Rourke is not likely to face a ton of preplanned attacks. A few weeks ago, opposing candidates might have criticized his lack of specificity, but recently O’Rourke has made a point of cranking out serious policy proposals on immigration, climate, and voting rights.

Cory Booker

What does he need to do? Booker has been building up a huge organization all over the country, but his polling still lags. He’ll likely make the case for why he should be considered a top-tier candidate, pitching himself as an electable, energizing, relentlessly positive change-maker who’s not afraid to work with Republicans if he needs to. He’ll likely look to engage Warren and O’Rourke directly, and could focus on his criminal-justice work to distinguish himself from the pack.

Whom might he attack? People who watch Booker casually often make the mistake of assuming that because he talks so much about love and tries to be so positive that he doesn’t go on the attack. That’s not true: When he wants to draw a contrast, he makes sure it’s as clear as possible. Just look at his recent back-and-forth with Biden over the former vice-president’s reminiscences about working with segregationist senators. If Booker’s going on the attack, it will likely be against Biden, who’ll be onstage the next night.

Who might attack him? No one has an obvious need to attack Booker, and he’s not likely to confront anyone he’s onstage with, but it’s possible Bill de Blasio could knock his Wall Street ties and Delaney does have his reasons for trying to damage him, too, since they’re two of the candidates making the biggest bets on Iowa.

Amy Klobuchar

What does she need to do? A huge part of Klobuchar’s pitch is that she can beat Trump — and that voters simply need to look at her electoral record in Minnesota to see the evidence. This will likely be at the center of her debate messaging, too, but she is also eager to break from the middle of the pack, so she may engage Warren — Wednesday’s biggest name — in policy discussions directly to elevate herself in voters’ eyes.

Whom might she attack? On the campaign trail, Klobuchar often points out how she can talk about certain issues — like agricultural ones, in Iowa — in a way none of her rivals can, but she rarely goes after them directly, and rarely by name. If that’s going to change on the debate stage, she would likely go after Sanders and anyone who she perceives might agree with his proposed style of governance. Klobuchar is known in the Senate as someone eager to cross party lines and make deals, so she may pounce on anyone who suggests that such bipartisanship isn’t possible.

Who might attack her? Klobuchar isn’t likely to come under direct attack.

Julián Castro

What does he need to do? Remind voters why he was labeled a rising star in the party nearly a decade ago. Castro has been running a policy-heavy campaign, and he’s likely to point that out to underscore how serious he is about effecting real change. If there’s one issue where he’ll focus his energy, it’s immigration.

Whom might he attack? Castro doesn’t often attack other candidates, but those who watch him closely suspect this debate may provide an opportunity to change that. He has held off criticizing his fellow Texan O’Rourke, but he may now view him as his primary obstacle to rising much further in the field and so could draw contrasts with him, perhaps on immigration policy. And while neither Sanders nor Biden will debate on Wednesday, Castro, 44, has often portrayed himself as a beacon of generational change, so he may highlight their age, and maybe Warren’s.

Who might attack him? No one is obviously aiming at Castro, but it’s possible Warren and Booker, both of whom have talked about housing policy, might needle him. Warren could also bring up suggestions that he was close with Wall Street interests during his time in Obama’s Cabinet, though that’s probably not how Warren will want to spend her time onstage, and it’s an accusation Castro has been eager to rebut.

Jay Inslee

What does he need to do? Inslee might have the most obvious plan of attack of anyone in the field because his campaign has the clearest orientation: climate, climate, climate. He will almost certainly talk about the climate crisis no matter what the topic, but as a former congressman and Washington’s two-term governor, he’s also plenty comfortable discussing other broad issues in the race and then making the pivot. His challenge will be explaining why his candidacy is so focused on one big issue. But, again, he has to do that every day on the campaign trail, so he has plenty of practice. He’ll look to force the rest of the field closer to his position and to shame them if they don’t follow.

Whom might he attack? The DNC, for not bowing to his pressure campaign to hold a climate-focused debate. But if he goes after any other candidate, it’ll likely be Biden, whose team has had to insist it’s not actually pursuing a “middle ground” climate policy.

Who might attack him? Attacking Inslee would be dangerous since he’s managed to turn himself into a symbol of taking the climate emergency seriously. It’d be a surprise if anyone goes after him.

John Delaney

What does he need to do? Delaney needs to explain who he is. The former congressman has been running for nearly two years now, and he’s getting decently well known in both Iowa and New Hampshire, where he’s spent a ton of time. But now he must convince a national audience that his moderate “I’m a former business owner” message is the right one for this moment.

Whom might he attack? He’s been going after socialism and Sanders, clearly seeing it as a path to national relevance, so it’d be a surprise if he stopped doing that in Miami, even if Sanders won’t be there to defend himself.

Who might attack him? Probably no one.

Tulsi Gabbard

What does she need to do? Gabbard is well known by two groups of people: serious Sanders fans, who remember when she quit her DNC vice-chairmanship in 2016 to endorse him, and voters interested in foreign policy, who are used to her noninterventionism. She’ll need to try to introduce herself as an agent of change without talking about her personal history or her travels to Syria too much.

Whom might she attack? Biden and the foreign-policy Establishment. That one’s a lock. But she could conceivably attack anyone in the race except probably Sanders, who helped facilitate her rise to national prominence in 2016.

Who might attack her? It’s unlikely anyone is entering the debate planning to attack Gabbard explicitly — she hasn’t made much of a mark so far, so why would they? — but it’s possible she could draw one of the better-known candidates into a one-on-one at some point.

Bill de Blasio

What does he need to do? De Blasio’s task is simple: try to explain to a national audience why he’s running. Then, if he gets enough time, he can try explaining what he’s done in the city.

Whom might he attack? Joe Biden.

Who might attack him? Probably no one.

Tim Ryan

What does he need to do? Ryan — a youngish congressman from the Youngstown, Ohio, area who’s also a yoga and mindfulness practitioner — has an unexpected story to tell, but he knows he’s going to have to force people to pay attention to him. Expect him to use his time onstage as a “nice to meet you” moment in which he portrays himself as a regular guy from a regular part of the country who can both win back Trump voters and sign on to the broader structural economic change some of the best-known candidates are talking about.

Whom might he attack? It’s possible Ryan will try to attack Sanders in vague terms, but that wouldn’t really fit his style or his need to focus on introducing himself to voters in a positive light.

Who might attack him? Given the limited time candidates have to share their own visions, it would be pretty surprising if anyone takes on Ryan, who’s not well-enough known to warrant it.

THURSDAY

Joe Biden

What does he need to do? Still leading everyone else in the polls, Biden will enter the week simply wanting to stay in front, likely by invoking Barack Obama as much as possible and reiterating his pitch for a return to pre-Trump normalcy. But Biden’s whole campaign is based around the notion that he’s the Democrats’ most electable option against Trump, so he likely will need to prove that he has learned from — and can get beyond — controversies about his positions on segregationist senators, the Hyde Amendment, the crime bill, Anita Hill, and so on. There’s basically no way this debate doesn’t feature a good amount of Biden on defense.

Whom might he attack? Biden has little incentive to do much attacking: He’s winning, so far, and wants to win over everyone else’s voters, not to antagonize them. But if he does determine that it’d be useful to hit out, it would likely be at Sanders; Biden’s jabbed at him in past speeches over his backing of democratic socialism. Most likely, however, that will happen down the line in a later debate.

Who might attack him? Almost everyone else, including the candidates debating the previous night. And he knows it.

Bernie Sanders

What does he need to do? Sanders has two major imperatives at this point in his campaign: Win back as many of his 2016 voters as possible and expand into new pools of voters wherever he can. He’ll likely try and do the first one by making his signature anti-Establishment pitch and pointing out how much of the political mainstream, including many of the candidates onstage, stands against him, thereby riling up Democrats and independents inclined to like him. He’s been trying to do the second by making the case that he’s electable in a race against Trump. He’ll probably say that directly, but he could also seek to undercut the idea that others — like Biden — would be broadly acceptable to the electorate.

Whom might he attack? If Sanders is going to attack anyone, it will be Biden, the only candidate who consistently beats him in polling. He’s been attacking Biden’s “middle ground” positions both implicitly and explicitly for weeks now, so the question is whether he feels like doing it now, onstage, or later in the contest, once the field is smaller. Signs point to now.

Who might attack him? Next to Biden, Sanders is likely to get the most flak. Biden could pounce, but Sanders is almost certainly going to have to defend himself against many candidates trying to pick apart his ideology and pointing to his age.

Kamala Harris

What does she need to do? Was Harris happy to be put on the same stage with Biden and Sanders? There’s an argument to be made that she should be: She is undoubtedly a top candidate, and she’s been hesitant to go after any rivals directly. So she could cement her top-tier status by letting Biden and Sanders snipe at each other and sailing above the turbulence as a reasonable unifier. If she pursues this strategy, though, she’ll need to be careful not to stay too far above the fray and risk being forgotten. But that’s hardly Harris’s style, and her opponents are expecting a fearsome debater — a safe bet, if her performances in the Senate Judiciary Committee and her prosecutorial background are any indication.

Whom might she attack? Harris probably isn’t planning to attack anyone, but if she does, it will probably be Biden, whom she criticized last Wednesday over his comments about working with segregationist Democratic senators. Biden also currently has the support of many voters Harris is looking to win over, particularly African-Americans in South Carolina.

Who might attack her? If anyone decides to take her on, it will probably be someone on her left going after her criminal-justice record. Sanders, perhaps.

Pete Buttigieg

What does he need to do? Buttigieg is, of course, the surprise of the field. A bona fide challenger for the nomination at 37 years old, he must prove that his lack of experience is surmountable. So he’ll try to prove his seriousness by discussing policy and foreign affairs and going toe-to-toe with the two front-runners. But Buttigieg probably doesn’t need to make a huge splash on the first-debate stage. Since expectations for his performance are already sky-high, he may just want to play it safe and make sure he’s still considered a top candidate by Thursday’s end.

Whom might he attack? Biden and Sanders. Buttigieg’s rise was based on his message of generational change, and it just so happens that the two 70-something favorites will be right there with him onstage.

Who might attack him? Attacking Buttigieg is a more difficult proposition than it might seem since he is widely liked. But he has some obvious vulnerabilities, including his youth, lack of experience, and his relative weakness among minority voters after his polarizing handling of police matters in South Bend, including a recent shooting that killed a black citizen. If any lesser-known candidate is eager to knock Buttigieg down a notch or two in the pecking order, those are the avenues to explore.

Kirsten Gillibrand

What does she need to do? More than maybe anyone else in the field, Gillibrand is still struggling to catch up to early expectations, when she entered the race pitching herself as a hero to women voters. She’s since largely been ignored, so she needs to remind voters why they might have thought so highly of her at first — perhaps by forcing her way into policy or “electability” conversations that will likely be dominated by the top four candidates on this stage. She might accomplish this by zeroing in on Biden as a representative of the old, stale way of doing business.

Whom might she attack? Maybe Sanders, but if Gillibrand has to pick only one person to go after, it’ll be Biden. Her fans and allies were happy to see her placed on the same stage as the ex-VP, because he — older, more moderate, male — provides a contrast with Gillibrand that she’d love to lean into. Expecting her to bash Biden for his flip-flop on the Hyde Amendment in recent weeks.

Who might attack her? She’s not chipping into anyone’s support or blocking any lesser-known candidates’ paths, so don’t expect her to be on the receiving end unless Eric Swalwell decides to go after her change of heart on gun control.

John Hickenlooper

What does he need to do? It would seem that Hickenlooper’s in a tough spot. He needs to explain not only why he’s not just another little-known white man and not just another Western governor but also why he’s the best candidate from Colorado (also the home of Michael Bennet). The former governor and mayor, though, has been one of the campaign trail’s most aggressive proponents of just-get-things-done moderation, and his task here is to both demonstrate that his perspective is a strong alternative to Sandersism and to send a message to more-moderate Democratic voters that Biden isn’t their only option. Hickenlooper isn’t always the snappiest speaker, but he’s never been shy about butting in and is almost certainly going to make sure his presence is felt onstage with a bunch of the race’s heavyweights — especially now that he’s decided to be the contest’s loudest opponent of socialism.

Whom might he attack? Don’t expect Hickenlooper to go too hard against Biden — for his long-shot plan to work, he needs the former VP’s voters. But he hasn’t been shy about taking on Sanders while stumping, and it would make sense to try to engage the Vermonter in a fight in order to elevate his own stature in viewers’ eyes.

Who might attack him? He’s no one’s obvious predator, but purely for entertainment value it would be fascinating to see him go head-to-head with Bennet, who was his chief of staff when Hickenlooper was the mayor of Denver. That, however, is just not realistic. Instead, Hickenlooper will be hoping he can get under Sanders’s skin and create some back-and-forths with him. It’s worked once.

Michael Bennet

What does he need to do? Explain to a national audience how his pitch differs from his former boss Hickenlooper’s, for a start, and then try to see if his Washington-is-broken message can resonate on what will likely be a fiery debate stage.

Whom might he attack? Bennet’s not much of a pugilist, but he could come out swinging against Sanders, whose disdain for compromise represents a lot of what the Colorado senator is running against. Like Hickenlooper and Swalwell, though, Bennet will need to distinguish himself from the pack, so it’s possible he’ll try to make a point by attacking Biden as unhelpfully nostalgic, as he did after Biden spoke of working with segregationist senators.

Who might attack him? Bennet, who’s widely liked in the Senate, isn’t high on anyone’s list.

Eric Swalwell

What does he need to do? Swalwell has been campaigning heavily on gun safety, so he’ll try to show that he’s the most serious candidate on the issue. But if average voters know him, it’s because of his ubiquitous presence on cable news as a commentator on the Russia probes. So his task is to turn that dynamic into a credible, coherent appeal.

Whom might he attack? Maybe Sanders or Gillibrand based on their histories with gun-control votes. Swalwell, who’s 38, might also draw a contrast with Biden and Sanders in generational terms, but that’s the better-known Buttigieg’s shtick, too.

Who might attack him? Probably no one, but if he does lay into Sanders or Gillibrand on guns, neither will hesitate to engage.

Andrew Yang

What does he need to do? Yang has a loud following online, but if he wants to be treated like a serious candidate, he needs to introduce himself more broadly. He’s said that just being on the debate stage will be enough to do so, but he’s going to hope he has enough time to talk up his signature policy proposals, too.

Whom might he attack? No one in particular; possibly the system.

Who might attack him? No one’s going to attack Andrew Yang.

¶ Marianne Williamson

What does she need to do? Williamson is a bit of a celebrity, but she still needs to get average Democratic voters to understand who she is, why she’s here, and why to take her seriously. She should focus on the last one.

Whom might she attack? Probably no one, but Williamson’s been running a pretty surprising campaign (the first surprise: that she’s running), so if she decides to join in on the Biden bruising, it wouldn’t be the shock of the night.

Who might attack her? No one’s going to attack Marianne Williamson.