HOUSTON—A deal for star guard Russell Westbrook could shift the NBA’s balance of power. A deadline trade for ace pitcher Zack Greinke might decide the Major League Baseball season. And the people responsible for these daring acquisitions happen to work a few blocks from each other.

Rockets general manager Daryl Morey and Astros general manager Jeff Luhnow have more in common than the location of their offices. They both have MBAs. They both found their way into sports after working at high-powered consulting firms. They both run their teams with a heavy emphasis on analytics and an enormous appetite for risk. The biggest difference between them is that Luhnow built the Astros roster that won the World Series in 2017, while the Rockets under Morey haven’t won a title.

Their shared philosophy has resulted in a series of blockbuster trades in pursuit of a championship. Not every move has gone smoothly. Morey watched one strategy blow up in spectacular fashion as the Rockets missed a staggering number of 3-pointers against the Golden State Warriors, and Luhnow faced scrutiny when he acquired closer Roberto Osuna after he’d been suspended for 75 games for violating MLB’s domestic violence policy.

But the reason that Morey and Luhnow have frequently clashed with the establishment in their sports is that most of their biggest gambles have paid off.

We invited these two executives to lunch here earlier this month to have a wide-ranging discussion about their jobs. It was a curious time for both teams. The Astros are perhaps the favorite to win the World Series as playoffs begin next week. The Rockets are starting training camp with the NBA landscape wide open for the first time in years. Morey ordered chicken marsala, Luhnow a salad topped with salmon, and off they went for the next 90 minutes.