J.D. Drew and the Curse of Talent

Drew is a quintessential Hall of Pretty Damn Good Players inductee. Should he have been something more?

Original template by Emily Scherer

Welcome back to the Hall of Pretty Damn Good Players — our tribute to the players who won’t make the Hall of Fame, but whose careers still tell us something interesting about how sports really work.

Today’s installment looks at former Cardinals, Braves, Dodgers and Red Sox outfielder J.D. Drew: a player who was, quite literally, Pretty Damn Good™… but rarely great, especially when measured against the towering expectations placed on him by almost everyone in the sport. So how do we remember a player who ended up just fine, yet somehow also felt like a huge letdown — and elicited outright hate from multiple fanbases across the league?

Let’s take a closer look at Drew’s story, and why talent can sometimes be a curse as much as a gift.

A native of tiny Hahira, GA,¹ Drew was a high school standout — known locally as a once-in-a-generation talent — and nothing less than a college baseball legend at Florida State. As a sophomore in 1996, he was a finalist for the Golden Spikes Award (given to the nation’s best amateur player) after hitting 21 HR in 69 games with a 1.267 OPS. Then he put up an even better season as a junior, with 31 HR, 100 RBI, 32 steals² and an absurd slash line of .455/.604/.961 (1.565 OPS) in 67 games. That time, Drew did earn the Golden Spikes — along with widespread hype as a future MLB superstar.

In particular, Drew’s sweet left-handed swing, five-tool skill set and seemingly limitless ceiling garnered comparisons to Mickey Mantle (!) in the lead-up to the 1997 MLB draft. But at the same time, Drew’s agent Scott Boras — who was already notorious for playing financial hardball — warned teams not to bother picking his client unless they were prepared to meet his asking price. And what was that ask, exactly? The number floated in media reports was $11 million, though Boras later insisted it was closer to $7.5 million.³ Either way, the message was clear: Drew wasn’t going to settle for merely the going rate of a top draft pick at the time.

Still, the Philadelphia Phillies took him anyway with the No. 2 overall pick, leading to one of the most contentious standoffs in MLB draft history. Boras and Drew rejected the team’s $3 million offer, claiming it fell well short of fair market value — and then things got truly strange. A contract was mailed to Drew’s parents instead of his last known address in Tallahassee, triggering a dispute over whether Philadelphia had technically tendered an “official” offer. The Phillies argued they had; Boras claimed otherwise and even threatened a lawsuit.

The league sided with the team, but the damage was done. Drew never signed as a Phillie, instead spending the summer with the independent St. Paul Saints. (He led the Northern League with an 1.149 OPS, in case you were wondering.) Meanwhile, his case became a referendum on baseball’s entire draft system — and a symbol of player leverage that some fans and executives weren’t ready to accept.