After all was said and done, Benson had a decent career, winning 70 games over nine seasons and earning nearly $39 million in the game. His final career ERA+ was 100, meaning he was mathematically, precisely, completely average, better than exactly half his peers and worse than the other half over the course of his career.
And yet he was never able to escape the aura of failure. He was always expected to be so much more.
A Georgia native, Benson was chosen first overall in the draft by the Pittsburgh Pirates in 1996 — the first Clemson athlete in any sport ever to be drafted with the first overall pick. He reached the majors in 1999 and won 11 games for a Pirates team that finished in third place, just five games below .500. Ironically, the Pirates' record that year, 78-83, was very similar to Benson's career mark, 70-75. Both Benson and his Bucs appeared poised for great things. But both collapsed.
Benson bounced from team to team, rarely healthy and only moderately effective, and his outspoken wife — Anna Benson, FHM Magazine's 29th sexiest woman in 2006 — overshadowed him on sports pages and blogs. He has effectively been out of the game since 2006 — he missed all of 2001, 2007, and 2008 with injury, and only pitched a combined 36 1/3 innings in 2009 and 2010, posting a 7.18 ERA. After his career-best 217 2/3 innings and 3.85 ERA in 2000, he never again pitched more than 201 innings or posted an ERA below 4.00.
He was far from the only bust in the 1996 draft, however. Other first-rounders taken that year include flameouts and mediocrities like Travis Lee, Adam Eaton(notes), Dee Brown, Eric Milton(notes), and Gil Meche(notes). The most successful first-rounder was Eric Chavez(notes), whose career was effectively shattered by injury by the time he was 28. (The best player taken in the draft was 23rd-rounder Roy Oswalt(notes).) By Wins Above Replacement, Benson was the sixth-most successful first-rounder, behind Chavez, Mark Kotsay(notes), Meche, Milton, and Jake Westbrook(notes) — not great for the first overall pick, but better than the 24 others taken in the round, including 10 who never reached the majors and seven more who posted zero or negative WAR during their brief careers.
Sadly, Benson actually stands out as one of the Pirates' few success stories during the 1990s. During the team's nearly two decade-long losing streak, the Pirates have been perhaps the worst-drafting team in all of baseball. Benson stands as the team's greatest draft success between 1992, when they drafted Jason Kendall(notes), and 2003, when they drafted Paul Maholm(notes). In between Kendall and Maholm, the team made 10 first-round picks; four failed to reach the majors, and four others posted negative WAR in their brief major league careers. The only other moderate success was Sean Burnett(notes), who has emerged as a pretty good setup reliever. By comparison with the others, Benson was an oasis of value in a wasteland of blown picks. (GM Cam Bonifay helmed the team from 1993 to 2001, and the franchise may still be reeling from the after-effects of his horrifying mismanagement, like the post-Bavasi Mariners. And his successor, Dave Littlefield, was just as bad.)
It was perhaps unfair to saddle so much on one man's slender shoulders. By the time Benson arrived, the Pirates had endured six straight losing seasons, and their minor league cupboard was mostly bare. The team's stars were Brian Giles(notes) and Jason Kendall, who kept the team competitive but by themselves were not enough to drive the team into October. Still, no starting pitcher is enough to singlehandedly push a team into contention. During his first two years as a Pirate, Benson made 63 starts and the team played 260 other games, though the team actually played better when he was off the mound, with a .462 winning percentage when other pitchers started but just a .429 winning percentage when he took the bump.
The Pirates were hardly alone in admiring that arm of his. He had tantalizing stuff, even if he rarely was able to harness it. In 2004, the Mets traded Ty Wigginton(notes) and Jose Bautista(notes) — yes, that Jose Bautista — for him, and soon thereafter gave him a three-year, $22.5 million extension. Two years later, they traded him to the Orioles for John Maine(notes) and Jorge Julio(notes). Even though he has hardly pitched since that one season in Baltimore in 2006, he was still able to secure one-year contracts from the Phillies, Rangers, and Diamondbacks in 2008, 2009, and 2010. Many fantasy owners were similarly tempted, only to be perennially frustrated by his inability to stay healthy.
Benson wasn't good and he wasn't bad. If he hadn't been drafted first overall, and hadn't been given that $22.5 million contract, saddled with expectations he could never match, he could have been a feel-good story, the athlete with a will to win but a body that betrayed him, who tried time and again to come back from injury after injury. He made seven trips to the DL in his nine seasons, including three stays on the 60-day DL, and missed three entire seasons due to injury. Considering his medical history, it's remarkable and admirable that he was able to make 200 starts, win 70 games, and pitch 1,243 2/3 innings. (His 70 wins place him in the top 800 of the all-time wins list.) He wasn't what many hoped he would be, but he had a long and moderately successful career in the game he loved.