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Rays top prospects of all-time: No. 11

After 20 years of Rays baseball, we’re counting down the top prospects in franchise history.

XM All-Star Futures Game
Desmond Jennings could’ve been a great Rays outfielder
Photo by Jamie Squire/Getty Images

Next up on the list of top Rays prospects of all-time is another position player. Unfortunately, injuries prevented him from reaching his potential in the big leagues.

20. SS Reid Brignac
19. RHP Matt White
18. RHP Chris Archer
17. RHP Wade Davis/LHP Jake McGee
16. RHP Jeremy Hellickson
15. 1B/LHP Brendan McKay
14. SS Tim Beckham
13. RHP Brent Honeywell
12. SS Willy Adames

11. OF Desmond Jennings

Acquired: No. 289 pick by Devil Rays (2006)

Baseball America Top-100 ranks: 6 (2009), 22 (2010), 59 (2007), 80 (2008)
(Devil) Rays Top-30 ranks: 1 (2009), 3 (2010), 5 (2008), 6 (2007), 30 (2006)
League Top-20 ranks: 1 (2007 South Atlantic League), 3 (2009 Southern League), 4 (2011 International League), 7 (2006 Appalachian League), 7 (2010 International League)

(Devil) Rays best tools: Best athlete (2007, 2008, 2009, 2010), Best defensive outfielder (2009, 2010), Best strike-zone discipline (2009, 2010), Best average hitter (2009), Fastest baserunner (2010)
League best tools: Most exciting player (2009 Southern League, 2010 International League, 2011 International League), Best defensive outfielder (2007 South Atlantic League, 2009 Southern League, 2010 International League), Best baserunner (2009 Southern League, 2010 International League), Fastest baserunner (2009 Southern League)

Jennings peaked as Baseball America’s No. 6 prospect after the 2009 season with Double-A Montgomery and Triple-A Durham. He seemed poised to join a dynamic outfield that featured Melvin Upton Jr. and Carl Crawford, although the latter would soon leave in free agency.

The outfielder certainly earned that long list of accolades, particularly the labels of most exciting player. He was the rare player who was called a five-tool talent and could live up to that billing. He was no raw and unfinished product either — at 22, he just played 132 games in the upper minors and was nearly major league ready.

In 2009, Jennings accomplished a rare feat that only nine players have done since — stolen 50-plus bases and accumulated 50-plus extra-base hits in one season. Quite a few of those players otherwise had mediocre seasons. Jennings did not. He batted .318 with a .401 on-base percentage, and he had as many walks as strikeouts. He was a complete player.

That wasn’t always the case, though. In fact, he may have been the least heralded amateur on this list. Of the players on this list, he was the lowest draft pick, waiting until the 10th round to hear his name called. His bonus was only $150,000, quite a bit less than what the numerous first rounders received. It doesn’t appear he even had a scouting report prior to the draft at BA. However, it did not take long for him to get noticed as a professional.

With Princeton in the Appalachian League, Jennings got off to a great start, stealing 32 bases in 56 games with a .277 average and .360 OBP. BA named him the No. 7 prospect in the league, noting his superior athleticism, advanced plate approach, and defensive acumen. He also earned the No. 30 spot on the organization’s Top-30 list. Only two of the nine players the team drafted before him were also ranked, and they were both top-50 picks.

Jennings earned his first Top-100 ranking the following season with Columbus in the South Atlantic League. The 20 year old had no problem adjusting to full-season ball, batting .315 with a .401 OBP and .465 slugging percentage in 99 games. He had 45 steals and 34 extra-base hits. He was named the league’s top prospect, but knee surgery cut his season short.

His 2008 season did not go quite as well. A back injury cost him the first two months of the season, and he only played 24 games before shoulder surgery ended his season.

That’s another aspect of his 2009 season that was crucial. It wasn’t just the five-tool performance that made him one of the top prospects in baseball — he was healthy. He played in 132 games, by far a career high. It appeared the only thing that could slow him down was his own body because opposing pitchers certainly were not.

Jennings returned to Durham to start 2010, but it was a late start. He missed time with a wrist sprain, and his shoulder was bothering him, as well. He played 109 games for the Bulls before finishing the season with the Rays, but he wasn’t the same player. He still batted .278 and got on base at a .362 clip, but he slugged under .400 for the first time since his pro debut. It’s not hard to imagine those injuries might have sapped his power.

Perhaps surprisingly, Jennings again found himself in Durham to start 2011. Crawford was gone, but with Sam Fuld’s solid play and the continued emergence of Matt Joyce, playing time in the corner outfield spots was limited. He eventually did reach the big leagues for good that season, and he made an impact. In 63 games, he batted .259 with a .356 OBP and .449 SLG, and he stole 20 bases in 26 attempts. He finished seventh in Rookie of the Year voting.

Unfortunately, that was the season he peaked in the majors. Over the next three seasons, Jennings managed to play in 394 games, so he wasn’t totally derailed by injuries. However, he still missed time here with a knee sprain or time there with a finger injury. Maybe those didn’t result in large chunks of games being missed, but little things constantly adding up can probably still take a toll on performance.

In 2015 and 2016, the injuries proved to be too much. Jennings only played in 93 games over those two seasons, missing large portions of time with various leg ailments. He was eventually released in Aug. 2016.

After his rookie campaign in 2011, Jennings played in 487 games total over five seasons, all for the Rays. He batted just .243 with a .318 OBP and .386 SLG, and his per-162-game average for steals was 25 in 32 attempts. He struck out more and walked less than his best minor league seasons, and even worse than the power not quite developing was that he never really hit for average the way he did in the minors either.

Jennings never did form that outfield with Crawford and Upton. That trio could have provided nightly highlights with great defense, speed, and a little bit of pop. Crawford and Upton soon left in free agency, and Jennings took over in center field before being supplanted by Kevin Kiermaier.

It’s hard to say exactly what went wrong with Jennings. Injuries were clearly a factor, but did those directly lead to his plate approach declining as a big leaguer? In addition to his physical gifts, that made him stand out from the pack as a prospect. In the post-Crawford seasons, he could have added a lot to the lineup, but he never did.