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Back in March, I began running down a list of the most disappointing prospects of all time (part one, part two, part three), setting out to chronicle an in-no-particular-order top 50. In honor of draft week, I am resuming the series after a long hiatus.

As with the first three segments, the emphasis here is not on wasted draft picks, but player who were, ironically, good picks, who showed promise early on in their professional careers and were acclaimed as top prospects, but who failed to follow those accolades with major-league success. They have been a mix of draft and pre-draft players, from a period when success came down to raw scouting ability and money, but mostly the former.

In each of the three segments, I have nominated a current player whom I believe now qualifies for this list, or is at least well on his way to carving out a place on it. Though this installment adds only a half-dozen players to the list, I have not broken with the practice. Unlike previous choices, I don’t expect today’s selections to be controversial.

Paul Wilson, RHP, Mets
Drafted 1994, First Round, First Overall
If anyone knows how it served the Mets’ developmental goals to have Wilson throw eight complete games and 186.2 innings at Double- and Triple-A in 1995, please raise your hands. That season was the climax for the Florida State ace, who was part of an ill-starred top-10 in the 1994 draft class—the players who followed him were Ben Grieve, Dustin Hermanson, Anthony Williamson, Josh Booty, McKay Cristensen, Doug Million, Todd Walker (who also appears in this series), C.J. Nitkowski, and Jaret Wright.

Prior to the 1996 season, we called Wilson, “Clearly the best pitching prospect in all of baseball.” In his prospects book, John Sickels wrote, “His stuff is exceptional: blazing fastball, inhuman slider, outstanding command of the strike zone. Tough, hard-nosed, intelligent. Healthy… The only weakness that I can see is that he’s a human being and not a robot.” The actual weakness was in a Mets organization that had pushed him so hard. After his overloaded 1995, during which he struck out 194 while walking only 44 for a 2.41 ERA, Wilson made the major-league rotation in 1996 and started the season’s third game. He had the misfortune to make his debut under manager Dallas Green, who had required the 23-year-old Al Leiter to throw 163 pitches in a start in 1989. Green didn’t do anything as blatantly irresponsible with Wilson, though allowing him to throw 121 pitches in 4.2 innings in the tenth start of his career probably qualifies.

Green was canned in August, and Wilson’s miserable record (4-10, 6.55 ERA) surely had something to do with it. He finished strongly under new skipper Bobby Valentine, posting a 1.91 ERA in six starts to end the season, but his career was already hanging by a thread: Wilson had missed most of the month of June with shoulder tendinitis, but though he came back to pitch the rest of the season, he underwent surgery for a torn labrum after the season. He pitched in just 20 games over the next four seasons, undergoing further procedures. His comeback with the 2000 Rays looked promising, but he no longer had the stuff to rise above league-average performance at best. Another labrum tear did him in for good in May, 2005.

Daryl Boston, OF, White Sox
Drafted 1981, First Round, Seventh Overall
Three outfielders—Joe Carter, Terry Blocker, and Kevin McReynolds—went off the boards before the White Sox took Boston out of Woodward High School in Cincinnati. Meanwhile, Tony Gwynn sat around until the sixth pick of the third round—one pick ahead of Chicago’s next turn (hindsight is, as you may have heard, 20-20). A five-tool talent, Boston could do everything on a baseball field, but he mostly did things in the minor leagues.

The White Sox rushed Boston along, getting him to Triple-A at 21. Their top team was at Denver, which seemingly supplied the cure for any shortcomings Boston might have had; in 1984, he hit .313/.390/.533 in 127 games there, spiking his power numbers with 19 triples and 15 home runs. He also stole 40 bases in 57 attempts. Though the environment undoubtedly helped Boston, he had made real progress: he drew 65 walks and struck out 82 times, whereas the previous season he had struck out 147 times while taking 58 walks in almost exactly the same number of trips to the plate.

He would never hit that well again. Boston made his major-league debut that year but failed to produce either then or in a 95-game trial in 1985, hitting .213/.254/.305 with three home runs and 18 walks in 130 games. Fellow left-handers were his Kryptonite. In those first two seasons he went 3-for-34 against them. He was a little better in a 56-game trial in 1986, but even here he got off to a quick start upon his promotion in August, then tailed off rapidly.

By 1987, Boston had spent all or parts of seven seasons in the minors without laying claim to a regular job. The White Sox kept him up after that, but he was purely a utility player. In 1990, after 500 games of .239/.294/.389 hitting, the White Sox put Boston on waivers and he was claimed by the Mets, for whom he did his best work, hitting a solidly above-average .266/.338/.429 in three seasons of semi-regular duty. He was gone from the majors at the age of 31.

Pete Incaviglia, OF, Expos
Drafted 1985, First Round, Eighth Overall
Here is the first of two examples of hubris in this fourth entry in the series. An insanely dominant player at Oklahoma State, Incaviglia hit 48 home runs in 75 games in his last season as an amateur and left college with the NCAA record for career home runs (100). “Inky” figured he was too good for the minor leagues and too much a Californian for Canada and would not sign. Stymied, the Expos dealt him to the Rangers for Bob Sebra and Jim Anderson. Texas manager Bobby Valentine put the 22-year-old slugger in the lineup as his cleanup hitter and left him there for most of the next three years.

On one level, Incaviglia had immediate success. He hit 30 home runs that year. However, he also led the league in strikeouts with 185, then the highest number of whiffs by anyone not named Bobby Bonds. An all-or-nothing hitter who also happened to be a miserable, lumbering outfielder, Incaviglia might have benefitted from the coaching (theoretically) available in the minors. He barely progressed from that first season, and it is a measure of the Rangers’ growing disenchantment that he was released late in March, 1991, a full season away from free agency. After leaving Texas, a combination of injuries and inadequacy quickly ended his days as a regular; his best showing came in 1993, when he .274/.318/.530 in 116 games for the pennant-winning Phillies. He couldn’t hold on to those numbers, and by 1995 he was forced to Japan. He returned to the majors in 1996 but finally found his way to the minors in 1997 and largely stayed there from then on.

Todd Van Poppel, RHP, Athletics
Drafted 1990, First Round, Fourteenth Overall  
Hubris II: The Braves, seemingly forever lost at sea, had the first overall pick in the 1990 draft, and Texas high schooler Van Poppel was thought to be the best prospect in the country. In meetings with the Braves, Van Poppel, advised by Scott Boras, made it clear that the Braves had best spend their pick elsewhere if they wanted to come out of the round with a player in their lunch box. The Braves wiped away their tears, selected Chipper Jones, and have been laughing ever since.

Uncertainty about Van Poppel’s signability dropped him all the way down to the A’s at number 14. The A’s had four first-round picks that year and spent them all on pitchers. This was subsequently characterized as the “Four Aces” draft. Sadly, they weren’t even four deuces. The A’s missed on all four—Van Poppel, Don Peters, Dave Zancanaro, and Kirk Dressendorfer. The culprit was mostly injuries, though in Van Poppel’s case, handling forced by his signing a major-league contract (along with a record-setting bonus) played a part—Van Poppel made his major-league debut in September, 1991 despite a showing at Double-A, highlighted by a 6.1-per-nine walk rate, that strongly suggested he wasn’t ready. Forced to grow up in public, Van Poppel was consistently pounded, putting up a 5.75 ERA in 104 games for the A’s. His 9.06 ERA of 1996 remains the highest in history for a pitcher with at least 90 innings pitched. Cut loose in 1996, he drifted between the majors and the minors; his career highlight was a couple of decent years of middle relief for the Cubs.

You could argue that Van Poppel should really be classified as a blown draft choice rather than a prospect disappointment. Given his great stuff and his ability to pitch effectively at times, I think he is deserving of the prospect label. With a little more seasoning and an earlier move to the bullpen, his career could have been very different.

Ron Necciai, RHP, Pirates
Pre-Draft, Signed 1950
On May 13, 1952, 19-year-old righty Necciai, pitching for the Pirates Class D club at Bristol (roughly the equivalent of Low-A), struck out 27 batters in a nine-inning game. On one hand, the game was a total fluke: even the best pitchers in the history of the game have never struck out 27 batters. On the other hand, the 6-foot-5 Necciai was a legitimate prospect, with a high-90s fastball and two different curves.  He was dominant in the minors in 1952, putting up a 1.28 ERA at two levels.

“I never realized I was striking out as many as I was because I would walk a guy, hit a guy, and I was bouncing a lot of balls off the screen and into the dirt,” Necciai told George Stone about his record-setting game. “I must have thrown 250 pitches that night.”

Yet, it wasn’t that night that derailed Necciai. After finishing the ’52 season with the desperate-for-anyone-good big-league Pirates, Necciai had his bid for a 1953 roster berth derailed by severe ulcers, followed by military induction, followed, finally, by the inevitable arm injuries. His 1-6 record in 12 games that fall would represent the beginning, middle, and end of his major-league career.

Brandon Wood, INF, Angels
 Drafted 2003, Twenty-Third Overall
The three still-young active players listed in this spot have been Alex Gordon, Matt Wieters, and Cameron Maybin. No one argued about Gordon or Maybin, though they probably should have, while seemingly the entire city of Baltimore took umbrage at my selecting Wieters. I remind you of the rationale behind these picks: each of these players gave some indication that he was correctly drafted, and that he was properly regarded as a coming star, only to fall short of that level.

Since I pointed a finger at Wieters, I’ve heard a great deal about what a fine defensive catcher he is. Granted, but so is Henry Blanco, and no one calls him a star. As for Wieters’ supposed offensive renaissance this season, sure, he’s been better than he was, but his current .274/.335/.408 is not, even when adjusted for context, dramatically different from the .266/.328/.393 rates he carried into the season. Gordon has made a much more convincing argument that I condemned him prematurely, as has Maybin, especially when his home-road splits are considered—he was hitting .316/.375/.532 away from Petco (and he should be back from knee tendinitis soon).

I don’t think anyone will argue about Wood. Now 26, Wood has had 572 major-league plate appearances, about a full season’s-worth, and has hit .174/.207/.265. He has walked just 19 times while striking out 170 times. He’s like Josh Booty, if Booty had done his act in the majors instead of the minors. Wood may be the worst hitter of the postwar period, and perhaps ever. Bill Bergen, a National League catcher of 1901-1911 and a reasonable pick for worst hitter of all time, had an OPS+ of 21. Wood isn’t too far off at 28, and that’s with his hitting .211/.273/.310 for the Pirates, a vast “improvement.”

The main argument one can make in Wood’s favor is that the Angels didn’t give him a long leash in any of his five auditions with the big-league club, although it’s hard to blame them given just what weak prey he was for pitchers. It also didn’t help that Wood, drafted as a shortstop, never mastered the position defensively. Perhaps what is most frustrating is that Wood’s minor-league numbers are so strong. He was a .284/.352/.536 hitter in the sticks, including his 2005 California League rampage: .321/.383/.672 with 53 doubles and 43 home runs in 130 games. As of today, it has taken Wood 200 games to hit just 12 home runs in the majors, and the chances that he will hit another 31 to equal what he did in one summer in Rancho Cucamonga seem remote indeed.

Thank you for reading

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It wasn't just Baltimore who roundly mocked your selection of Wieters; it was a wide range of rational baseball analysts who were stunned someone would mistake a solid career start with a historic bust. In reality, his 2011 is on pace to be worth 4.5 wins in his age 25 season. Not exactly busty...
I didn't say "busty," I said "disappointing." He's not a bust, he's just not living up to expectations legitimately generated both by his status going into the draft and his exceptional minor-league performances. As I have stated repeatedly, this series is NOT about busts, but about players who seemed to be coming stars only to fail to achieve that level of success. Wieters could still turn out to be quite a useful player--he is one--and not meet expectations. Imagine if Joe DiMaggio had come to the Yankees having hit .398 for the San Francisco Seals and turned out to be Lastings Milledge. Then he would be on this list too.
Don't worry, Steve. Those of us who know how to read understand what you're getting at.
The best argument against including active players is Phil Nevin, who would have undoubtedly made this list at this point, but his 30+ career resurgence seems to exclude him now.
I thought you were going to lead with all 3 members of "Generation K" (I guess Izzy wouldn't qualify for your list, though)
Regarding Wilson, I don't know how a guy can be considered disappointing or a bust when the organization he was working for abused him until he broke down.
Still waiting for you to call Rich Dauer's number.
I don't know that I would call Dauer a bust; he was a good defensive second baseman who provided doubles power with the occasional home run. Perhaps the expectations were higher as he was a 1st round draft pick but the Orioles got 6 pretty decent seasons from Dauer, out of the 10 that he played.
He was a disappointing bust because the organization he worked for abused him until he broke down. What, a guy can't be a bust unless it's his own fault??
Somebody in the game must know something specific that can explain Wood's complete combustion. There appears to be such a thing as a 4A player, but this is something beyond that. If he is such an easy victim in the majors, seemingly for any sort of pitcher who comes along, it's hard to understand why so few in the minors were able to get him out. Pitches in the minors do have some tools, after all, and that seems to be all it takes.
Incaviglia was interesting in that he's responsible for the rule that you can't trade a draft pick for a year after he signs. The commish's office wasn't happy about the position he put the Expos in, and so instituted the rule to give the clubs more leverage.
Matt Wieters is certainly no bigger a bust than BP's PECOTA projections for him.
Pretend the projection never happened. His season was huge, regardless of what we said its implications meant for his future. He didn't compile those numbers at High Desert--Wieters wasn't Matt Mieske 1991. Whatever spin should have been put on those numbers, they weren't going to vanish altogether.