Cubs outfielder Brett Jackson continues to be one of the most perplexing prospects in baseball. He’s a toolsy outfielder with speed and power, but he carries with that a strikeout rate that is rarely seen. Jackson’s 59 strikeouts in 120 big league at-bats last season is even more rare than you may think. With a strikeout in 49.17 percent of his at-bats, Jackson posted the second-highest rate ever by a position player in a big league season of 100 or more at-bats.

Only Athletics catcher Dave Duncan’s 49.5 percent rate in 1967 tops Jackson’s 2012 propensity to swing and miss. With a 100 at-bat cutoff, there have only been 35 players to strike out in 40 percent or more of their at-bats in a season since the integration era began in 1947. It was a very disappointing big league debut for Jackson, who has ranked in the top 40 in each of the past two Baseball America Top 100 Prospect lists.

So can Jackson put his free-swinging ways behind him enough to have big league success? If he does, he’ll be part of a select group. Looking at the players who have come close to Jackson’s 2012 big league strikeout rate finds plenty of players either on their way out of the league or those who never really arrived. A few players who posted similar rates early in their big league careers managed to have some success, but in most cases they were able to succeed because they had another tool, usually massive power or excellent glove work behind home plate, to make up for their offensive deficiencies. If Jackson is able to overcome his strikeout problems to become more than a role player or second division regular, he'll be bucking history.

Here's a look at past players with a similar strikeout rate in the big leagues.
The Success Stories

Dave Kingman, of, Giants, 1973. Whiff Rate: 40%. Kingman’s massive amount of strikeouts and his less-than-cheery disposition made him more famous than his always potent power. He led the league in home runs twice and hit 442 total, showing that his high strikeout rate early in his career wouldn't keep him out of the lineup.

Rob Deer, of, Giants, 1985. Whiff Rate: 43.8%. Traded to the Brewers after his rough rookie season (he hit .185/.283/.277), Deer was a Three True Outcomes star over his remaining eight seasons. He piled up plenty of home runs (230 for his career), lots of walks and a massive amount of strikeouts—he led the league five times.

Kelly Shoppach, c, Indians, 2006. Whiff Rate: 40.9%. Shoppach ranked on the Red Sox Top 10 Prospects lists for four seasons and appeared at No. 78 on the BA Top 100 Prospects list in 2004 before being traded to the Indians in time to join Cleveland’s big league club in 2006. Shoppach’s defensive ability (coupled with a career .868 OPS versus lefties) has allowed him to get plenty of work as a part-time catcher, but his strikeouts have kept him from ever being an everyday catcher. Hhe’s played in more than 100 games only once in eight big league seasons, and that came about because of an injury to starter Victor Martinez. But he does have more power than the average platoon catcher and he has been a big leaguer for seven seasons.

Russ Branyan, 3b, Indians, 2001. Whiff Rate: 41.9%. Branyan makes several appearances on this list, as even at his best he balanced on a very narrow margin between striking out too much to play, or providing enough power and defense at third base to allow a team to put up with his strikeouts. His power was legendary–and explains why he made three Top 100 Prospect appearances. But Branyan's strikeouts and the resulting career .232 batting average and .329 on-base percentage also explain why he's topped 300 at-bats only four times in 14 big league seasons.

Failed To Meet Expectations

Billy Ashley, of, Dodgers, 1995. Whiff Rate: 40.9%. Ashley’s power potential helped him make a pair of Dodgers Top 10 Prospects lists in 1993 and ’94, but he never made enough contact to succeed at the big league level. Ashley never had 300 at-bats in a season and last played in the big leagues as a 27-year-old.

Brad Eldred, 1b, Pirates, 2005. Whiff Rate: 40.5%. Eldred ranked ninth on the Pirates Top 10 Prospects list heading into the 2005 season, and he was considered to have the club’s best power potential. But even 12 home runs in 55 big league games and a .458 slugging percentage weren’t enough to get the Pirates to overlook his problems with contact. Eldred has had a couple of cups of coffee in the big leagues since ’05, but he’s been largely relegated to being a Triple-A slugger.

Mat Gamel, 3b, Brewers, 2009. Whiff Rate: 42.2%. Gamel’s defensive problems were what got the most notice during his rookie season with the Brewers, but his strikeout problems have helped keep him from establishing himself as a big league regular. A knee injury ruined his chances to replace Prince Fielder at first base in 2012, and now he heads into the 2013 season hoping to be a versatile backup for Milwaukee. It’s a pretty steep drop for a prospect who ranked among the Brewers’ Top 10 Prospects for four straight seasons and ranked No. 34 in all of baseball heading into 2009.

The Jury Is Still Out

While most of the players in the past to record 40 percent or worse strikeout rates were either lumbering sluggers or glove-first catches, there are a couple of current players who come much closer to matching Jackson’s profile as a speedy center fielder with contact problems.

Justin Maxwell, of, Nationals, 2010. Whiff Rate: 41.4%. Maxwell has battled plenty of injuries, but he made five Nationals Top 30 Prospects lists and cracked the Top 10 on two occasions. Washington gave up on him after he hit .144 in 2010 and placed him on waivers once he ran out of minor league options. He got another chance in the big leagues with the Astros this past season. Now 28, he hit 18 home runs, but still struck out in 36 percent of his at-bats, which explained his .229/.304/.460 line.

Trayvon Robinson, of, Mariners, 2011. Whiff Rate: 42.7%. Most of the players with the highest strikeout rates are either glove-first catchers or players with 30+ home run potential. Like Jackson, Robinson came up to the big leagues as a speedy center fielder with average power to go with excellent speed. Robinson made the Dodgers’ Top 10 Prospects lists twice, in 2009 and ’10, before being traded to the Mariners in 2011. In parts of two big league seasons, he’s failed to hit for enough power to make up for his large number of strikeouts, and he’s largely been limited to left field. The Mariners traded him to the Orioles this offseason for Robert Andino.

Tyler Flowers, c, White Sox, 2012. Whiff Rate: 41.2%. Like Shoppach, Flowers has more power than the average catcher, but his swing for the fence approach means he struggles to get on base when he doesn't get to jog around the bases. The White Sox appear ready to give him a shot at an everyday job in 2013, but his career .205 batting average and .307 on-base percentage in 273 big league at-bats is a cause for concern.

Here's the list of every big league position player to post a strikeout rate of 40 percent or worse in 100 or more at-bats since 1947, the data is courtesy of Baseball Reference's Play Index.