The Coulda, Woulda, Shoulda Of Rays First Round Picks

The Rays have made first-round picks in 20 drafts so far.  Today, we'll look at who Tampa Bay made their first pick of the draft, and who they could have selected in that same spot.


Did draft: OF Josh Hamilton (1st overall)

Should have drafted: RHP Josh Beckett (2nd, Marlins)

Hamilton had all the tools to be a monster at the big-league level, but his issues with drugs kept him off the field until he was taken away from the Rays in the Rule 5 Draft before the 2007 season.  He eventually became a five time All-Star and the 2010 American League Most Valuable Player with the Rangers.  Meanwhile, Beckett reached the big leagues in 2001, won 138 games in his career, struck out nearly 2,000 hitters, and won two World Series.


Did draft: OF Rocco Baldelli (6th overall)

Should have drafted: 2B Chase Utley (15th, Phillies)

Rocco has become one of the most recognizable faces in the franchise's history, and showed how great his baseball acumen is as a player, coach, on scout, but health issues derailed his playing career.  Meanwhile, the 39-year-old Utley is playing in his 18th season in the bigs, with eight of his teams making the postseason.


Did draft: RHP Dewan Brazelton (3rd overall)

Should have drafted: 3B Mark Teixeira (5th, Rangers)

He's the subject of one of the most famous sound bites in this station's history (Brazelton, B-r-a-z-e-l-t-o-n), but Dewan finished just 8-25 in five seasons in the majors.  Meanwhile, the switch-hitting infielder wrapped up his playing career with 409 homers in 14 seasons, and has become a great baseball analyst on ESPN.


Did draft: SS B.J. Upton (2nd overall)

Should have drafted: RHP Zack Greinke (6th, Royals)

Upton was a big part of the Rays success from 2008 through 2012, but passing up a chance to draft one of the top pitchers of this generation (a Cy Young Award, three ERA titles, four All-Star Games) could be one of the biggest regrets the scouting department could have.


Did draft: OF Delmon Young (1st overall)

Should have drafted: OF Nick Markakis (7th, Orioles)

Drafting Young eventually helped the Rays deliver the 2008 American League pennant, as trading him brought both Matt Garza and Jason Bartlett, but could you imagine what an outfield with Carl Crawford and Markakis would have looked like?


Did draft: RHP Jeff Niemann (4th overall)

Should have drafted: RHP Jered Weaver (12th Angels)

If this were the NBA, Niemann would have been a no-brainer (because you can't teach tall), but this is baseball, and Niemann's delivery and all the moving parts that went along with it, caused him to have a bunch of shoulder issues that ended his career early.  Meanwhile, Weaver went to three All-Star games and finished in the Top 5 in Cy Young voting three times while winning 150 games in 12 seasons.


Did draft: RHP Wade Townsend (8th overall)

Should have drafted: OF Andrew McCutchen (11th, Pirates)

Niemann's teammate from Rice turned down $2.2 million the year before from the Orioles to finish up his degree, and that may have been a wise choice, as the right-hander failed to get above the AA level.  meanwhile, the Fort Meade outfielder became the face of the Pittsburgh Pirates franchise, making the All-Star team five times, winning four Silver Slugger awards, and being named the National League MVP in 2013, plus he just happened to end the team's 20-season playoff drought in the process.


Did draft: 3B Evan Longoria (3rd overall)

Should have drafted: Longoria

Longoria became the face of the Rays that the franchise needed.  He arrived early in 2008, winning the Rookie of the Year Award, and helping power the team not only to their first postseason berth, but all the way to the 2008 World Series.  He left the team via trade after the 2017 season leading the team all-time in almost every offensive category.


Did draft: LHP David Price (1st overall)

Should have drafted: Price

The left-hander got the save in Game 7 of the 2008 American League Championship Series, which was the first of a number of accolades he'd receive with the team before his departure at the trade deadline in 2014.  The first Cy Young Award winner for the team?  That's Price.  The first 20-game winner?  Price too.  He finished with 82 wins, a 3.18 ERA and 1065 strikeouts.


Did draft: INF Tim Beckham (1st overall)

Should have drafted: C Buster Posey (5th, Giants)

I know I say that there is no way that the Rays would have been able to sign Posey if they took him first overall, but there's also no doubt that Posey has been the cream of the crop in that first round draft class, thanks to his Rookie of the Year win in 2010, MVP in 2012, and five All-Star Game appearances.


Did draft: 2B LeVon Washington (30th overall)

Should have drafted: 3B Nolan Arenado (59th, Rockies)

Washington would not sign with the team, the only time the team would fail to ink their top pick.  He'd be selected by the Indians in the second round a year later, and would never get above High-A ball.  Meanwhile, all Arenado has done in his six years in the bigs is win the Gold Glove every year, make three All-Star teams, and hit 37 homers and drive in 130 in each of the last three years.


Did draft: OF Josh Sale (17th overall)

Should have drafted: RHP Noah Syndergaard (38th, Blue Jays)

The outfielder will be more known for his social media posts (including one made famous by our own Ronnie Lane -- "Big booty is my kryptonite") than anything he ever did on the field, washing out at the High-A level.  Syndergaard has dealth with his share of injuries, but is widely considered an top-level pitcher.


Did draft: RHP Taylor Guerrieri (24th overall)

Should have drafted: OF Mookie Betts (172nd, Red Sox)

The 2011 draft saw Tampa Bay get ten selections in the first 90 picks, and came away with just one big leaguer (Blake Snell).  Meanwhile, Betts had to wait until the fifth round to hear his name called, and has taken it out on the other 29 teams since arriving in the big leagues as retribution.


Did draft: 3B Richie Shaffer (25th overall)

Should have drafted: RHP Lance McCullers, Jr. (41st, Astros)

Shaffer made it to the majors with the Rays for a cup of coffee, but has faded back into obscurity while failing to break out full-time.  McCullers, a standout from Jesuit High School, already has an All-Star Game appearance and a World Series ring on his finger.


Did draft: C Nick Ciuffo (21st overall)

Should have drafted: OF Aaron Judge (32nd, Yankees)

Ciuffo has slogged through the Rays minor-leagues (and dealt with a 50-game suspension for testing positive for weed a second time), finally getting to the Triple-A level this year.  Meanwhile, the Yankees took Judge 11 picks later to help Brian Cashman keep the snowball rolling downhill with drafted and developed talent.


Did draft: 1B Casey Gillaspie (20th overall)

Should have drafted: 3B Matt Chapman (25th, Athletics)

He was dubbed "The Great Gillaspie" thanks to a strong spring in 2017, but struggled at the Triple-A level with Tampa Bay before being traded to White Sox at the trade deadline for Dan Jennings.  He's struck out 52 times in 138 at bats so far this year at Triple-A and was outrighted off Chicago's 40-man roster.  Chapman has emerged at the next great defensive third baseman, though his offense has yet to catch up.


Did draft: OF Garrett Whitley (13th overall)

Could have drafted: INF Scott Kingery (48th, Phillies)

Whitley has shown flashes of why the Rays drafted him in the first round, but shoulder surgery cost him the entire 2018 season at the High-A level.  Meanwhile, Kingery has already made it to The Show and signed a six-year, team-friendly deal with the Phillies.  


Did draft: 3B Josh Lowe (13th overall)

Could have drafted: SS Bo Bichette (66th, Blue Jays)

Lowe, along with his brother Nate could be a great 1-2 punch for Tampa Bay, but Toronto has a 1-2-3 core of Bichette, Vlad Guerrero Jr., and Cavan Biggio (son of Hall of Famer Craig Biggio) that could be the best second-generation grouping we'll see in a long time.


Did draft: 1B/LHP Brendan McKay (4th overall)

Could have drafted: McKay

McKay and Shohei Otani are the only two players to be in the top hitting and top pitching prospects this year, and McKay has already gone from Bowling Green to Charlotte, and could end the year in Double-A.  If that's the case, a cup of coffee in the big leagues wouldn't be out of the question in 2019.

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