After graduation, Rocco moved back to New York and got a gig at one of the biggest restaurants of the '90s, Lespinasse, under famous Swiss chef Gray Kunz, who called him "concentrated, focused, and quiet," but impressive enough to be offered two executive chef jobs, one at Dava, and one at Annabelle. Both restaurants failed under his stewardship, but on September 30, 1994, in a brief Diner's Journal review, New York Times food critic Ruth Reichl gushed about a calamari salad at Annabelle, mentioning in the last sentence of her second paragraph that "the restaurant's chef, Rocco DiSpirito, is someone to watch."
A year later, restaurateurs Steven Scher and Jeff Kadish realized that it was the '90s and that they had to buy rollerblades and open an Asian-fusion place. Rocco cooked for them and they offered him the job the next day, and, in 1997, Union Pacific opened its doors -- though the food wasn't Asian fusion as much as it was unadulterated Rocco creativity. "The owners were trying to ride this Asian fusion wave," says Pete Wells, "and they got this wonder boy and, for a while, they didn't really know what to make of him." In her first review of the place, Ruth Reichl awarded him two stars. But a year later, in August 1998, Reichl revisited the young chef she'd been watching. Talking to her today, she still remembers her meal. "Most of the time, you're eating copycat food, and you can tell the influences right off the bat," Reichl says. "But eating Rocco's dishes, I thought, 'My god, he's cooking from some other place, out of his head.' The food was shockingly unique. As a critic, you're dying to find chefs like him." Impressed, Reichl went home and penned a three-star review, mentioning that she had "yet to taste anything on Mr. DiSpirito's menu that is not wonderful."