Editor’s Note: This story was included in The Athletic’s Best of 2019. See the full list.



CLEARWATER, Fla. — It was less than six hours before the Phillies agreed to the richest deal in American sports history and John Middleton was running late. He had stayed awake as Wednesday bled into Thursday to type notes from his two contentious phone conversations with Scott Boras. The basics of those discussions had already been relayed to the club’s top executives. That is why Matt Klentak, the general manager, went to sleep thinking that Bryce Harper would never wear red pinstripes.



Now it was Thursday morning and Middleton was driving to Spectrum Field while Pete Buck, another of the team’s owners, was on the phone. There was an unbridgeable gap, Middleton told Buck through his car’s speaker. The deal was dead. Then, Middleton’s phone rang.



“Oh my God,” Middleton said to Buck. “It’s Scott...