For essentially three years, every Grand Slam has represented a huge chance for Serena Williams to make history. First, she spent 2014 trying to catch the 18 majors of Chris Evert and Martina Navratilova, finally doing so in New York to finish the Slam season. That led into the second Serena Slam and pursuit of the Calendar Year Slam in 2015, and even though she came up short, she started this year with two more chances to tie Steffi Graf’s Open Era record of 22, both spoiled.
This Wimbledon, however, presents different stakes for Williams. While the upside of winning still remains, coming up short at The Championships would mark the first time since 2008 that a healthy Serena (that 2011-2012 stretch deserves an asterisk) is not an active holder of a Slam.
Also, the No. 1 ranking is seriously up for grabs. Even if she hangs onto it into autumn, her sabbatical post-U.S. Open last year (and subsequent absence of ranking points) would mean she’d surely fall at some point. With young stars like Garbiñe Muguruza and Madison Keys making their mark with deep runs that, while infrequent, put their ATP counterparts to shame, if Williams is forced to hand over the top spot, there’s no guarantee she’d get it back.
SERENA WILLIAMS  QUARTER
Contenders: Serena Williams, Timea Bacsinszky, Sloane Stephens, Coco Vandeweghe, Kiki Mladenovic
Big name, little chance: Roberta Vinci (has lost seven straight matches on grass dating back to 2013, only a Slam contender at the U.S. Open), Svetlana Kuznetsova (hasn’t made even the fourth round since 2008), Anastasia Pavyluchenkova (has an 8-9 losing record at Wimbledon and hasn’t made the fourth round at any Slam since 2011)
Notable floaters: Caroline Wozniacki, Yulia Putintseva, Christina McHale, Timea Babos, Heather Watson, Monica Niculescu, Aleksandra Krunic
Best first round match: Kuznetsova vs Wozniacki
This is perhaps the most orderly quarter of the draw. A tip-top contender in Williams finds herself lumped with a host of quality third tier contenders there to capitalize if she slips. Mladenovic gave Williams a handful in Paris and has had a quality grass season, while Stephens can push her if she’s in the right headspace. Vandeweghe beat Mladenovic for the title in the Netherlands and backed that up with a win over Aga Radwanska in Birmingham. The floaters here, led by Wozniacki, are deep but more potent on other surfaces for the most part.
AGA RADWANSKA  QUARTER
Contenders: Aga Radwanska, Belinda Bencic, Petra Kvitova, Johanna Konta, Dominika Cibulkova, Barbora Strycova, Caroline Garcia
Big name, little chance: Andrea Petkovic (a slumping Petko is just 14-15 on the year and Wimbledon is the one Slam where she’s never reached the quarters)
Notable floaters: Genie Bouchard, Monica Puig, Dasha Gavrilova, Sorana Cirstea, Ekaterina Makarova, Tsvetana Pironkova
Best first round match: Bencic vs Pironkova, Kvitova vs Cirstea, Konta vs Puig; it’s too hard to pick between these stellar matchups
If Serena’s quarter is tiered evenly, Radwanska’s quarter is like one big game of hectic laser tag. A savvy grass player like Bencic still looks rusty after her back injury, while Kvitova remains as unpredictable as ever even if she is healthy.
Konta, Cibulkova, Strycova, Garcia and Puig all had strong grass results in the past couple weeks and any one of them could remain hot into the second week. Radwanska’s consistency and grass pedigree make her the top pick but just as with Angie Kerber’s French Open quarter, there’s legitimately a dozen options to survive into the semis. Buckle up.
ANGIE KERBER  QUARTER
Contenders: Angie Kerber, Simona Halep, Madison Keys
Big name, little chance: Karolina Pliskova (made the Eastbourne final this weekend but her Slam struggles continued with a first round exit in Paris), Sara Errani (clay couldn’t turn her year around, as she went winless in the Madrid/Rome/French Open stretch, so she certainly won’t be a threat on her worst surface), Ana Ivanovic (signs of her decline: hasn’t played a tour final since January 2015 and has lost early so often that she’s faced just one top 10 opponent this season)
Notable floaters: Jelena Ostapenko, Alize Cornet, Nicole Gibbs, Kirsten Flipkens, Laura Siegemund, Louisa Chirico, Misaki Doi, Laura Robson, Zarina Diyas
Best first round match: Kerber vs Robson
This quarter is very hard to get a feel for due to having both Kerber and Halep. At their best, they are excellent two-way players whose emotional momentum can carry them to high peaks. That momentum goes the opposite way too, though. When the ship goes south, it can sink fast.
Kerber is the better grass player, but Halep did make the semis here in 2014, rolling her ankle in a loss to Genie Bouchard. Their starts could determine if this quarter has some blockbuster matchups or if Madison Keys could have a cakewalk. Kiki Bertens and Irina-Camelia Begu are here as well, looking to follow up breakthroughs on clay.
Keys is, well, the key in this quarter. Grass is the Birmingham champion’s self-professed favorite surface, and other than maybe Flipkens, her path to the second week is a breeze. Her three Wimbledon results? third round (Radwanska), third round injury retirement (Shvedova) and quarterfinal last year (Radwanska again), all very defensible. The 21-year-old already has 22 wins on the lawn and is poised to add to that total.
GARBIÑE MUGURUZA  QUARTER
Contenders: Garbiñe Muguruza, Venus Williams, Carla Suarez Navarro, Jelena Jankovic
Big name, little chance: Sam Stosur (not inconceivable she could make it to the second week here for the first time, but even a severely slumping Sabine Lisicki is an unpleasant second round matchup), Elina Svitolina (3-7 career on grass against a manageable slate of opponents), Dasha Kasatkina (has made an impressive push with a 20-12 record on the year, but grass is too much to ask of her at this stage)
Notable floaters: Sabine Lisicki, Camila Giorgi, Julia Goerges, Shelby Rogers
Best first round match: Muguruza vs Giorgi
Easily the weakest quarter of the draw, this section is both light on dependable seeds and dangerous floaters, making it a shock if Muguruza or the elder Williams didn’t come out of it. Giorgi and Lucie Safarova are tricky opponents but if Muguruza is really the Next Big Thing, she can’t allow them to stand her way. If Williams has an off-day (a great possibility given her age, despite a surprising run in Paris), Muguruza could easily defend her finalist points from 2015.
With how stacked the other quarters are, one had to take the hit and, barring Lisicki finding her old form for her annual run, it’s felt here. There’s just not a ton of intrigue.
Round of 16: S. Williams, Stephens, Bacsinszky, Vandeweghe, Radwanska, Cibulkova, Strycova, Pironkova, Halep, Keys, Diyas, Kerber, V. Williams, Jankovic, Lisicki, Muguruza
Quarterfinals: S. Williams def Bacsinszky, Radwanska def Pironkova, Keys def Kerber, Muguruza def V. Williams
Semifinals: S. Williams def Radwanska, Keys def Muguruza (have to hedge against a post-Slam letdown for Garbi)
Final: Gulp. I hate jumping on the hype train too early but this draw is ripe with opportunity for young Madison Keys. She takes her first Grand Slam, beating Serena in the final, with Serena coming up just shy of Slam No. 22 yet again.