A review by jeanstehle
The Winner by Teddy Wayne

dark emotional mysterious tense medium-paced
  • Plot- or character-driven? Character
  • Strong character development? Yes
  • Diverse cast of characters? It's complicated
  • Flaws of characters a main focus? Yes

4.5

Whoa! This book!

THE WINNER by Teddy Wayne is a wild exploration of privilege, identity, and the price of success set against the backdrop of an exclusive summer community on the coast of Massachusetts.

I was pulling for the main character, Connor O'Toole, from the moment I met him. He hustled his way through life thanks to his intellect, work ethic, and mentorship of a tennis instructor. 

Now all Connor needs to do this summer is make bank by giving tennis lessons to Cutter's Island's tony residents and prepare to take the bar. 

Connor's hopes for his future are noble. His priority is to provide a comfortable life for his ailing, widowed, unemployed mother. When a divorcée client of Connor's proposes an offer he cannot refuse, Connor sees no harm in making a little more money off the court.

What follows is a nail-biting journey into the depths of privilege and wealth Cutter's Island residents rely on for survival. 

Perhaps Connor will finally catch a lucky break and make this world his own. But when you uncover the dark deeds he’s willing to commit, will you still be rooting for him??