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A Draft Do-Over for Every MLB Team
May 2, 2020A Draft Do-Over for Every MLB Team
- No Mike Trout: Everyone knows that Mike Trout was the 25th pick in the 2009 draft, and that 21 teams passed on the best player in the game today in the process. We're looking for some fresh takes here, so Trout was excluded from this exercise.
- Each Player Once: A case can be made that the biggest regret for the Atlanta Braves, Seattle Mariners, Philadelphia Phillies and St. Louis Cardinals was passing on a hulking Auburn University slugger named Frank Thomas in 1989. However, each player was only eligible to appear once.
- First-Round Picks Only: If a superstar slipped out of the first round, that means even the team that did wind up drafting him missed on him at least once. We're only looking at first-round picks here.
- Realistic Draft Position: To add another layer of realism to this exercise, a do-over could only be used on a player who was chosen within the next 10 picks of where a team was drafting. In theory, that limited it to players who were on a team's draft board when they made their pick.
It's time for another round of MLB revisionist history.
A few weeks ago, I published an article titled "How Every Team Would Use a 21st-Century Do-Over" that explored how each club would use a mulligan if given the chance. The only exception was there was no altering the MLB draft.
Now it's time for that side of the discussion.
With the 21st century restriction lifted, we took a look back through each team's full draft history dating back to the first amateur draft in 1965 and dug up one regrettable decision that each team would love to reverse.
First, a few ground rules:
Got all that?
Let's get started.
Arizona Diamondbacks
The Draft: 2010
The Squandered Pick: RHP Barret Loux, No. 6 overall
The Missed Opportunity: LHP Chris Sale, No. 13 overall
There were six pitchers selected before Chris Sale went No. 13 overall in the 2010 draft.
Jameson Taillon (No. 2), Drew Pomeranz (No. 5) and Matt Harvey (No. 7 overall) have gone on to varying levels of MLB success; Deck McGuire (No. 11) flamed out in the minors; and both Barret Loux (No. 6) and Karsten Whitson (No. 9) failed to sign.
The D-backs made the Loux selection, eventually opting against signing him after he failed a post-draft physical.
"The (mistakes) that really gnaw at me and I still wake up thinking about are the ones in the draft," Jerry Dipoto, who was vice president of scouting and player development for the D-backs in 2010, told reporters. "Where you had a scout or multiple scouts in the room telling you, 'This is the guy.' You know, 'We should take Chris Sale.' We should have."
Sale has gone on to post more career WAR (45.3) than those other six pitchers combined (29.1).
One can't help but wonder if having Sale in the rotation would have prevented the Zack Greinke signing, which might have in turn saved the team enough money to extend Paul Goldschmidt or re-sign Patrick Corbin.
Atlanta Braves
The Draft: 1989
The Squandered Pick: C Tyler Houston, No. 2 overall
The Missed Opportunity: 1B Frank Thomas, No. 7 overall
The Baltimore Orioles selected LSU right-hander Ben McDonald with the No. 1 overall pick in the 1989 draft, and while he didn't go on to have a Hall of Fame career, he did enjoy a solid nine-year run in the majors.
After that, things get messy.
Tyler Houston (No. 2 to Atlanta), Roger Salkeld (No. 3 to Seattle) and Donald Harris (No. 5 to Texas) combined for 0.2 WAR in the majors, while Jeff Jackson (No. 4 to Philadelphia) and Paul Coleman (No. 6 to St. Louis) never reached the majors.
That brings us to the No. 7 pick, where the Chicago White Sox selected University of Auburn slugger Frank Thomas after he hit .403/.568/.801 with 19 home runs and 83 RBI in 64 games during his junior season.
Had the Braves grabbed him at No. 2 overall, they would have likely never made the trade for Fred McGriff at the 1993 deadline that stands as one of the best moves in franchise history.
So at least there's that.
Baltimore Orioles
The Draft: 2006
The Squandered Pick: OF Billy Rowell, No. 9 overall
The Missed Opportunity: RHP Max Scherzer, No. 11 overall
Evan with Evan Longoria (No. 2 overall) and Clayton Kershaw (No. 7 overall) already off the board, the Baltimore Orioles still had a chance to grab a future star with the No. 9 pick.
Instead, they chose prep third baseman Billy Rowell.
He hit .328/.415/.503 with 25 extra-base hits in 53 games after signing but failed to build off that strong debut. He never advanced beyond Double-A, and his pro career ended in 2011.
One pick later, the San Francisco Giants selected two-time Cy Young winner Tim Lincecum.
Two picks later, the Arizona Diamondbacks chose three-time Cy Young winner Max Scherzer.
Meanwhile, the closest thing the Orioles have had to an ace since Mike Mussina left for New York in 2001 is guys like Erik Bedard, Jeremy Guthrie, Chris Tillman and Wei-Yin Chen.
Boston Red Sox
The Draft: 1995
The Squandered Pick: RHP Andy Yount, No. 15 overall
The Missed Opportunity: RHP Roy Halladay, No. 17 overall
The Boston Red Sox saw more of Roy Halladay over the course of his Hall of Fame career than any other team in baseball, as he made 39 starts and tossed 275 innings against them in his 16 MLB seasons.
Turns out, they could have seen far more of him.
With the No. 15 pick in the 1995 draft, the Red Sox selected Texas prep right-hander Andy Yount, who ended up being one of three players chosen among the first 17 picks to never reach the majors.
Yount was the second high school pitcher selected that year, behind only Kerry Wood, who went No. 4 overall to the Chicago Cubs.
Two picks later, Roy Halladay became the fourth.
A few years later, the Red Sox lost a heart-breaking ALCS to the New York Yankees in 2003.
That same year, Halladay won AL Cy Young honors, going 22-7 with a 3.25 ERA in 266 innings. That pick may very well have changed the course of history and brought the Red Sox that long-awaited title a year earlier.
Chicago Cubs
The Draft: 1988
The Squandered Pick: 2B Ty Griffin, No. 9 overall
The Missed Opportunity: 3B Robin Ventura, No. 10 overall
The Chicago Cubs used eight different Opening Day third basemen from the time Ron Santo departed following the 1973 season until Vance Law earned the nod in 1988. That year's draft provided them with a golden opportunity to bring that revolving door to a halt.
When their turn to draft came at No. 9 overall, Oklahoma State third baseman and Golden Spikes winner Robin Ventura was still on the board. He hit .391 with 26 home runs and 96 RBI during his junior season, and his impressive resume included an NCAA record 58-game hitting streak.
Instead, the Cubs selected Georgia Tech second baseman Ty Griffin, with the hopes of moving him to third base since his natural position was occupied by Ryne Sandberg.
Griffin, a Team USA standout, went on to hit .241/.366/.372 over five minor league seasons, never advancing beyond Double-A.
The crosstown Chicago White Sox scooped up Ventura with the next pick, and he went on to play 10 seasons on the South Side and 16 seasons total in the majors. He won six Gold Glove Awards and earned two All-Star selections on his way to 56.1 career WAR.
The hot corner remained a black hole for the Cubs until Aramis Ramirez was acquired at the 2003 trade deadline.
Chicago White Sox
The Draft: 1985
The Squandered Pick: C Kurt Brown, No. 5 overall
The Missed Opportunity: OF Barry Bonds, No. 6 overall
The 1985 draft was loaded with collegiate talent.
Will Clark (Mississippi State), B.J. Surhoff (North Carolina), Barry Larkin (Michigan), Barry Bonds (Arizona State) and Bobby Witt (Oklahoma) were all in the mix to go No. 1 overall, and they all wound up off the board within the first six picks.
Prep catcher Kurt Brown is all that kept them from going 1-5 when he was chosen by the Chicago White Sox with the No. 5 overall pick.
He spent seven seasons in the White Sox's minor league system and eventually reached Triple-A, but he never made his MLB debut before his professional career came to a close in 1991.
The college star who slipped out of the top five? Barry Bonds.
That's how close the White Sox were to having Bonds and Frank Thomas share a lineup during the early 1990s.
Cincinnati Reds
The Draft: 1992
The Squandered Pick: OF Chad Mottola, No. 5 overall
The Missed Opportunity: SS Derek Jeter, No. 6 overall
Five teams passed on Derek Jeter in the 1992 draft, but it's the Cincinnati Reds who are always mentioned as the team that was this close to selecting him.
Scout Gene Bennett has given his account of the infamous decision to go with UCF outfielder Chad Mottola with the No. 5 overall pick, which went against his firm belief the team should choose Jeter, and it's worth a read if you're not familiar with the story.
At any rate, Mottola posted an .831 OPS with 21 home runs and 91 RBI at High-A in his first full season, before struggling in the upper levels of the minors. He played 35 games for the Reds in 1995 and a grand total of 59 games at the MLB level.
Considering Hall of Fame shortstop Barry Larkin hung around through the 2004 season, the Reds would have needed to convince either Larkin or Jeter to shift to second base at some point during the mid-'90s when Jeter was knocking on the door.
That's a conversation the Reds would have been happy to have.
Cleveland Indians
The Draft: 1971
The Squandered Pick: RHP David Sloan, No. 9 overall
The Missed Opportunity: OF Jim Rice, No. 15 overall
From 1968 until their legendary 1995 campaign, the Cleveland Indians never won more than 84 games in a season.
Hall of Fame outfielder Jim Rice might have helped.
Chosen No. 15 overall in the 1971 draft, Rice finished second in AL Rookie of the Year voting in 1975 and spent his entire 16-year career with the Boston Red Sox. He posted a 128 OPS+ with 382 home runs and 1,451 RBI, earning eight All-Star nods and winning 1978 AL MVP honors.
The Indians are one of 13 teams that no doubt regret passing on him, with the lone exception being the California Angels (left-hander Frank Tanana at No. 13).
Prep right-hander David Sloan wound up being the pick for the Indians.
He was the fifth pitcher selected and one of four players chosen in the top 10 who never reached the majors.
Colorado Rockies
The Draft: 2007
The Squandered Pick: RHP Casey Weathers, No. 8 overall
The Missed Opportunity: LHP Madison Bumgarner, No. 10 overall
Would Madison Bumgarner have enjoyed the same level of success pitching at Coors Field?
For a team that counts Ubaldo Jimenez as arguably the best pitcher in franchise history, he would have been a welcome addition to the staff, even as a fraction of the pitcher he would eventually become for the San Francisco Giants.
With collegiate standouts David Price (Vanderbilt), Daniel Moskos (Clemson) and Ross Detwiler (Missouri State) already off the board at No. 8 overall, the Colorado Rockies had their pick of that year's crop of high school arms.
Instead, they continued the run on college arms, selecting Vanderbilt right-hander Casey Weathers, who went 12-2 with a 2.37 ERA and 75 strikeouts in 49.1 innings while saving seven games in 31 relief appearances.
After a solid first full season in 2008, he underwent Tommy John surgery and never returned to form.
The Arizona Diamondbacks made Jarrod Parker the first prep arm taken at No. 9 overall before the Giants snagged Bumgarner with the No. 10 pick.
For his career, Bumgarner is 16-8 with a 3.27 ERA in 35 starts against the Rockies.
Detroit Tigers
The Draft: 2014
The Squandered Pick: OF Derek Hill, No. 23 overall
The Missed Opportunity: 3B Matt Chapman, No. 25 overall
The future is bright for the Detroit Tigers on the pitching side of things, with Casey Mize, Matt Manning and Tarik Skubal each ranked among the top pitching prospects in baseball.
However, the team is sorely lacking in long-term position-player talent.
Toolsy outfielder Derek Hill was drafted on the strength of his plus speed and standout defensive skills in the outfield, with the hope that his bat would eventually catch up.
"Combining well above-average speed with defensive instincts makes Hill the top defensive center fielder in the draft class. He has plus range and made highlight-reel grabs on the showcase circuit," wrote Baseball America in his predraft scouting report.
Alas, he has hit just .243/.313/.349 in 477 minor league games, though he has swiped 156 bases along the way. He may yet develop into a useful fourth outfielder, though he has yet to advance above Double-A.
Meanwhile, Matt Chapman could be a franchise cornerstone in Detroit.
The slick-fielding, power-hitting third baseman from Cal State Fullerton went off the board to Oakland two picks later, and he has racked up 16.6 WAR with a pair of top 10 finishes in AL MVP voting the past two seasons.
Houston Astros
The Draft: 2013
The Squandered Pick: RHP Mark Appel, No. 1 overall
The Missed Opportunity: 3B Kris Bryant, No. 2 overall
With Alex Bregman manning third base, the Houston Astros don't necessarily need Kris Bryant.
However, they could have easily moved the big slugger to a corner outfield spot, which would have prevented the need to sign Josh Reddick in free agency.
Regardless, the current makeup of the roster does little to ease the sting of Mark Appel flaming out.
The Stanford University standout rebuffed the Pittsburgh Pirates as the No. 8 overall pick in the 2012 draft, returned to campus, and boosted his stock enough to go No. 1 overall the following year.
However, in his first full professional season, Appel was shelled the tune of a 6.91 ERA. He rebounded the following season with a 4.37 ERA in 131.1 innings in the upper levels of the minors, but it was backed by a less-than-stellar 110-to-51 strikeout-to-walk ratio, and the Astros had seen enough.
He was traded to the Philadelphia Phillies during the 2015-16 offseason as part of a five-player package to acquire Ken Giles, and he stuck around through the 2017 season, never reaching the majors and finishing his minor league career with a 5.06 ERA in 375.1 innings.
Kansas City Royals
The Draft: 2006
The Squandered Pick: RHP Luke Hochevar, No. 1 overall
The Missed Opportunity: LHP Clayton Kershaw, No. 7 overall
There is always risk involved with high school pitchers.
That said, there was also plenty of risk surrounding eventual No. 1 overall pick Luke Hochevar heading into the 2006 draft.
After failing to sign as the No. 40 overall pick in the 2005 draft, he signed on with the Independent League's Fort Worth Cats rather than returning to the University Tennessee for his senior season.
He showed enough in four indy ball starts for the Kansas City Royals to use the No. 1 overall pick in the 2006 draft on him, ahead of college standouts Andrew Miller (North Carolina), Tim Lincecum (Washington) and Brad Lincoln (Houston).
However, it's the risk they didn't take on a prep left-hander from Highland Park High School in Texas that stands as one of the biggest regrets in franchise history.
Five other teams passed on Clayton Kershaw before he went No. 7 overall to the Los Angeles Dodgers, but it's the Royals who had the first crack at selecting him.
Los Angeles Angels
The Draft: 1967
The Squandered Pick: C Mike Nunn, No. 9 overall
The Missed Opportunity: C Ted Simmons, No. 10 overall
Ted Simmons was the third catcher selected in the 1967 draft.
The two chosen before him—Johnny Jones (No. 5 overall to Senators) and Mike Nunn (No. 9 overall to Angels)—never reached the majors.
Nunn hit .209/.304/.299 with a 28.1 percent strikeout rate and 14 home runs in 1,159 plate appearances over six minor league seasons, just three of which were spent in the Angels organization.
Meanwhile, Simmons became the St. Louis Cardinals' starting catcher in 1971, hitting .304/.347/.424 for a 114 OPS+ in 563 plate appearances to finish 16th in NL MVP voting.
He went on to slug 248 home runs and tally 1,389 RBI over 21 MLB seasons, earning eight All-Star selections on his way to Hall of Fame enshrinement.
The best catcher in Angels history: Bob Boone? Maybe, Bengie Molina?
Los Angeles Dodgers
The Draft: 1983
The Squandered Pick: LHP Erik Sonberg, No. 18 overall
The Missed Opportunity: RHP Roger Clemens, No. 19 overall
The 1983 draft was a strange one.
The Minnesota Twins chose Tim Belcher with the No. 1 overall pick but failed to sign him.
Five of the first 15 picks never reached the majors, and among players who did sign, only two eclipsed 10 WAR for their career.
One was Milwaukee Brewers left-hander Dan Plesac (16.9), who went No. 26 overall. He saved 158 games and earned three All-Star selections over the course of a solid 18-year career.
The other was Roger Clemens.
That means 18 teams squandered an opportunity to draft one of the best pitchers in baseball history, so the Los Angeles Dodgers are by no means alone in wishing for this do-over.
One pick before Clemens was chosen by the Boston Red Sox, the Dodgers took Wichita State left-hander Erik Sonberg. He had a 6.20 ERA in 432.2 innings in the minors and never reached the majors.
Just imagine a staff of Orel Hershiser and Clemens on the same Dodgers staff in the late '80s.
Miami Marlins
The Draft: 1995
The Squandered Pick: OF Jaime Jones, No. 6 overall
The Missed Opportunity: 1B Todd Helton, No. 8 overall
The fledgling Florida Marlins had little in the way of long-term building blocks in just their third year of existence in 1995.
However, one of their more productive players was 25-year-old first baseman Greg Colbrunn, who hit .277 with 23 home runs and 89 RBI during the 1995 season.
Perhaps that's why the front office decided to pass on University of Tennessee first baseman Todd Helton, who was still on the board at No. 6 overall. He went on to slug 369 home runs with 2,519 hits and 1,406 RBI in 17 seasons with the Colorado Rockies.
They instead selected high school outfielder Jaime Jones, and he wound up being the highest pick from the 1995 draft class to never reach the majors.
Two years after passing on Helton, the Marlins traded ace Kevin Brown to the San Diego Padres as part of their memorable post-World Series fire sale. First baseman and top prospect Derrek Lee was the headlining piece of the return package.
Had Helton been manning first base, they would have been able to address a different area of need with that blockbuster trade.
Milwaukee Brewers
- Mark Mulder (No. 2, OAK): 20.0 WAR
- Jeff Austin (No. 4, KC): -0.7 WAR
- Ryan Mills (No. 6, MIN): Did not reach majors
- J.M. Gold (No. 13, MIL): Did not reach majors
- Jeff Weaver (No. 14, DET): 15.2 WAR
- Clint Johnston (No. 15, PIT): Did not reach majors
- Kip Wells (No. 16, CWS): 8.0 WAR
- Brad Lidge (No. 17, HOU): 7.9 WAR
- Seth Etherton (No. 18, ANA): -0.7 WAR
- CC Sabathia (No. 20, CLE): 62.5 WAR
The Draft: 1998
The Squandered Pick: RHP J.M. Gold, No. 13 overall
The Missed Opportunity: LHP CC Sabathia, No. 20 overall
Concerns over his limited remaining projection and potential weight issues down the line caused CC Sabathia to slip to No. 20 overall in the 1998 draft.
There were nine pitchers in all selected before Sabathia:
Each of those five teams in bold could easily point to passing on Sabathia as a significant regret.
However, the Milwaukee Brewers get the nod because they eventually went out and traded for him, sending future All-Star Michael Brantley to the Indians in the process.
Minnesota Twins
The Draft: 1991
The Squandered Pick: 1B Dave McCarty, No. 3 overall
The Missed Opportunity: OF Manny Ramirez, No. 13 overall
Manny Ramirez had eight seasons over the course of his 19-year career where he hit more than 36 home runs, en route to 555 for his career.
The Cleveland Indians selected him with the No. 13 pick in the 1991 draft.
That was 10 picks after the Minnesota Twins drafted Stanford first baseman Dave McCarty.
He went on to hit a grand total of 36 home runs in his 11-year career, posting minus-2.1 WAR while serving mostly as a bench player.
The 1991 draft as a whole was a mess.
Eight of the first 10 picks failed to produce 1.0 WAR at the MLB level, led by two of the biggest busts in draft history: touted prep left-hander Brien Taylor (NYY) and Golden Spikes winner Mike Kelly (ATL).
New York Mets
The Draft: 1966
The Squandered Pick: C Steve Chilcott, No. 1 overall
The Missed Opportunity: OF Reggie Jackson, No. 2 overall
The New York Mets made a decision that altered the MLB landscape when they selected catcher Steve Chilcott with the top pick in the 1966 draft.
The California prep standout is one of just three No. 1 overall picks to never reach the majors before retiring, along with Brien Taylor (1991) and Mark Appel (2013).
With the No. 2 pick that year, the Kansas City Athletics chose future Hall of Famer Reggie Jackson.
He made his MLB debut the following year and quickly emerged as a central figure on the Athletics teams that would go on to win three straight World Series titles from 1972 to 1974.
Who did they beat in the 1973 World Series? The Mets.
To make matters worse, Jackson went 9-for-29 with three doubles, one triple and one home run to win World Series MVP honors.
New York Yankees
The Draft: 2001
The Squandered Pick: SS Bronson Sardinha, No. 34 overall
The Missed Opportunity: 3B David Wright, No. 38 overall
After Graig Nettles departed following the 1983 season, the New York Yankees shuffled through a number of third basemen in the years to come.
Among the more notable names were Mike Pagliarulo, Wade Boggs, Charlie Hayes, Scott Brosius and Robin Ventura before they pulled off a blockbuster deal to acquire Alex Rodriguez prior to the 2004 season.
Had they scooped up David Wright with the No. 34 pick in the 2001 draft, they would not have needed to break the bank on A-Rod.
While he didn't debut until midway through the 2004 campaign, Wright was the No. 21 prospect in baseball heading into that season, and he was already knocking on the door.
He wound up hitting .293/.332/.525 for a 119 OPS+ with 17 doubles, 14 home runs and 40 RBI in 69 games, and just like that a new star was born in New York.
How do the two players stack up?
From 2005 through the 2013 season, Wright was worth an impressive 44.4 WAR. During that same span, Rodriguez was worth 44.6 WAR, and he took home nearly $200 million more in salary.
Oakland Athletics
The Draft: 1997
The Squandered Pick: RHP Chris Enochs, No. 11 overall
The Missed Opportunity: 1B/OF Lance Berkman, No. 16 overall
Despite a deep 1997 draft class, the Oakland Athletics were one of three teams who drafted in the top 15 and wound up with a player who never reached the majors when they chose West Virginia right-hander Chris Enochs with the No. 11 pick.
In that sense, the New York Mets (Geoff Goetz, No. 6 overall) and Florida Marlins (Aaron Akin, No. 12 overall) could point to this same missed opportunity as a significant regret.
However, this one cuts a bit deeper for the Athletics, considering Lance Berkman would have been the perfect replacement for Jason Giambi.
After winning AL MVP honors in 2001, Giambi bolted in free agency, signing a seven-year, $120 million deal with the New York Yankees.
At that same time, Berkman was coming off a breakout 2001 season where he hit .331/.430/.620 for a 161 OPS+ with 55 doubles, 34 home runs and 126 RBI. He was playing outfield at that point, before shifting to first base later in his career.
Instead, the A's replaced Giambi with the likes of Scott Hatteberg, Dan Johnson and Daric Barton in the years to come.
Philadelphia Phillies
The Draft: 1973
The Squandered Pick: C John Stearns, No. 2 overall
The Missed Opportunity: OF Dave Winfield, No. 4 overall
The 1973 draft featured a pair of future Hall of Famers in Robin Yount and Dave Winfield, who went off the board with the No. 3 and No. 4 overall picks, respectively.
That means two teams royally blew it.
It's hard to fault the Texas Rangers for selecting prep left-hander David Clyde with the No. 1 overall pick.
He had the stuff to jump straight from high school to the majors, but he was horribly mishandled by the organization. While the initial plan was to give him two starts in the big leagues before sending him to the minors, he ended up starting 18 games in the second half and tacking 93.1 innings onto the total he had already accumulated during his senior year.
Not surprisingly, arm issues derailed his career.
With the No. 2 pick, the Philadelphia Phillies drafted catcher John Stearns, who went on to have a solid 11-year career, posting 19.7 WAR and earning four All-Star selections.
Still, if they were given a do-over, Winfield would have been wearing a Phillies uniform.
The only reason Winfield gets the clear nod over Yount is that Larry Bowa was a solid option at shortstop for the Phillies during that same era.
Pittsburgh Pirates
- Bryan Bullington (No. 1, PIT): -0.2 WAR
- Chris Gruler (No. 3, CIN): Did not reach majors
- Adam Loewen (No. 4, BAL): -0.3 WAR
- Clint Everts (No. 5, MON): Did not reach majors
The Draft: 2002
The Squandered Pick: RHP Bryan Bullington, No. 1 overall
The Missed Opportunity: RHP Zack Greinke, No. 6 overall
This is another example of a missed opportunity for multiple teams.
There were four pitchers selected ahead of Zack Greinke in the 2002 draft, with Melvin Upton Jr. sandwiched between them at No. 2 overall to the Tampa Bay Rays:
Yikes.
Bullington was the top college arm out of Ball State, while the other three were plucked from the high school ranks.
The Pirates had a tough time developing pitching talent in the 2000s, so there's no telling if Greinke would have become the same pitcher had he started his career in Pittsburgh.
Still, it's hard not to look back on this decision with regret if you're a Pirates fan.
San Diego Padres
The Draft: 2004
The Squandered Pick: SS Matt Bush, No. 1 overall
The Missed Opportunity: RHP Justin Verlander, No. 2 overall
Right-hander Jered Weaver (Long Beach State) and shortstop Stephen Drew (Florida State) were arguably the top players on the board heading into the 2004 draft.
However, both players were represented by agent Scott Boras, and that was enough to scare off several teams. They ended up going No. 8 and No. 15 overall, respectively, and each received a $4 million signing bonus.
By comparison, the Padres gave prep shortstop Matt Bush a $3.15 million bonus as the No. 1 pick, plucking him from their own backyard at Mission Bay High School in San Diego.
However, there was another top-tier option available.
With the No. 2 pick, the Detroit Tigers selected Old Dominion standout Justin Verlander, inking him to a nearly identical $3.12 million bonus. He went on to become one of the top pitchers of his generation and would easily be the best pitcher in Padres franchise history.
Meanwhile, on-field struggles and off-field issues resulted in Bush never reaching the majors with the Padres, though he would later reinvent himself as a pitcher with the Texas Rangers.
San Francisco Giants
The Draft: 2015
The Squandered Pick: RHP Phil Bickford, No. 18 overall
The Missed Opportunity: RHP Walker Buehler, No. 24 overall
There are plenty of recent options for the San Francisco Giants, who have had a rough go of it in the first round since hitting on Madison Bumgarner (2007), Buster Posey (2008) and Zack Wheeler (2009).
However, the chance to steal a budding star away from their biggest rivals i too good to pass up.
Heading into his junior season, Walker Buehler was viewed by most talent evaluators as the top 2015 draft prospect on a Vanderbilt roster that also included eventual No. 1 pick Dansby Swanson and No. 8 pick Carson Fulmer.
He wound up slipping to No. 24 overall because of elbow issues, and he underwent Tommy John surgery at the onset of his pro career.
The Dodgers took the risk, and now they are reaping the rewards. The 25-year-old is one of the best young pitchers in baseball, fresh off a ninth-place finish in NL Cy Young voting, and he would be the perfect centerpiece of the Giants' current rebuild.
Phil Bickford, who has yet to pitch above High-A, was ultimately used as part of the trade package to acquire Will Smith at the 2016 trade deadline. So that's something.
Seattle Mariners
- Ryan Zimmerman (No. 4, WAS)
- Ryan Braun (No. 5, MIL)
- Troy Tulowitzki (No. 7, COL)
- Andrew McCutchen (No. 11, PIT)
- Jay Bruce (No. 12, CIN)
- Jacoby Ellsbury (No. 23, BOS)
- Matt Garza (No. 25, MIN)
- Colby Rasmus (No. 28, STL)
The Draft: 2005
The Squandered Pick: C Jeff Clement, No. 3 overall
The Missed Opportunity: SS Troy Tulowitzki, No. 7 overall
The 2005 draft was one of the most loaded classes in history.
Justin Upton (ARI) and Alex Gordon (KC) went off the board before the Seattle Mariners were on the clock, but there were still plenty of future stars available. Here's a look at some of the others who were selected in the first round that year:
Who did the Mariners draft?
USC catcher Jeff Clement, who hit .218/.277/.371 in 421 plate appearances in the majors while posting an ugly minus-1.2 WAR for his career.
Any of those players would have been a considerable upgrade for the Mariners, but we'll go with Tulowitzki for the re-do selection. The shortstop position has been a hole in Seattle since Alex Rodriguez walked in free agency.
St. Louis Cardinals
The Draft: 2000
The Squandered Pick: OF Shaun Boyd, No. 13 overall
The Missed Opportunity: 2B Chase Utley, No. 15 overall
For the most part, the St. Louis Cardinals have done an exceptional job drafting and developing talent over the years.
This is one glaring exception.
The 2000 draft as a whole was one of the weaker classes in recent memory, with seven of the first 14 picks failing to reach the majors and only Adrian Gonzalez (43.6) and Rocco Baldelli (10.1) even reaching the 1.0-WAR mark among the seven who did.
With the No. 15 pick, the Phillies took UCLA second baseman Chase Utley, who goes down as one of the best second basemen in MLB history.
Meanwhile, second base was a position of constant shuffling for the Cardinals throughout the 2000s, and Utley would have provided some welcome stability and additional offensive punch alongside Albert Pujols, Jim Edmonds and Scott Rolen.
Instead, he spent several years stuck behind Placido Polanco in Philadelphia, waiting until his age-26 season in 2005 to become an everyday player in the big leagues.
Tampa Bay Rays
The Draft: 2008
The Squandered Pick: SS Tim Beckham, No. 1 overall
The Missed Opportunity: C Buster Posey, No. 5 overall
Earlier this week, I put together an article selecting the all-time lineup for all 30 MLB teams.
With 41.8 WAR, an NL MVP, batting title and three World Series rings among the highlights of his impressive career, Buster Posey was the obvious pick at catcher for the San Francisco Giants.
The catcher pick for the Tampa Bay Rays was also fairly easy.
With 5.7 WAR and an 81 OPS+ over parts of seven seasons, Toby Hall was by far the best option at the position in franchise history. That speaks volumes to what a black hole the catcher spot has been since the team's inception in 1998.
Turns out, they could have had Posey.
After hitting an absurd .463/.566/.879 with 26 home runs and 93 RBI in 68 games during his junior season at Florida State, Posey entered the 2008 draft as arguably the best collegiate catching prospect ever.
He had to wait until No. 5 overall to hear his name called, while the Rays used the No. 1 overall pick on Tim Beckham, who was worth 1.1 WAR in 238 games with the team.
Texas Rangers
The Draft: 1990
The Squandered Pick: LHP Dan Smith, No. 16 overall
The Missed Opportunity: RHP Mike Mussina, No. 20 overall
Just imagine how good those 1990s Texas Rangers teams with Juan Gonzalez, Ivan Rodriguez, Rafael Palmeiro, Dean Palmer and Rusty Greer would have been if they just had some pitching.
Had they made the right pick in the 1990 draft, they would have had a bona fide ace.
With six pitchers already drafted, the Rangers selected Creighton University left-hander Dan Smith at No. 16 overall.
Smith pitched a total of 29 innings in the majors between the 1992 and 1994 seasons, posting a 4.66 ERA and 1.93 WHIP in two starts and 15 relief appearances.
Four picks later, the next pitcher off the board was Stanford right-hander Mike Mussina.
Mussina went on to win 270 games and post 82.8 WAR in a Hall of Fame career. He was 18-13 with a 3.64 ERA and 1.12 WHIP in 37 starts against the Rangers.
Toronto Blue Jays
The Draft: 1982
The Squandered Pick: SS Augie Schmidt, No. 2 overall
The Missed Opportunity: RHP Dwight Gooden, 5 overall
Dwight Gooden took the baseball world by storm in 1984 when he went 17-9 with a 2.60 ERA in 218 innings while leading the NL in WHIP (1.07), strikeouts (276) and FIP (1.69) as a 19-year-old rookie.
That same season, the Toronto Blue Jays finished 89-73 in second place in the AL East standings.
Would they have made a run at the playoffs with Gooden pitching alongside Dave Stieb (16-8, 2.83 ERA) and Doyle Alexander (17-6, 3.13 ERA)?
The next season, the Blue Jays won 99 games and a division title but fell to the Kansas City Royals in the ALCS in seven games.
Gooden won the NL pitching Triple Crown by going 24-4 with a 1.53 ERA and 268 strikeouts in 276.2 innings, taking home NL Cy Young honors in the process.
Would the Blue Jays have made it to the World Series with him on the staff?
Regardless, he would have been a better pick at No. 2 overall than Augie Schmidt, who hit .257/.350/.338 over five seasons in the minors before calling it a career.
Washington Nationals
The Draft: 1978
The Squandered Pick: SS Glen Franklin, No. 9 overall
The Missed Opportunity: OF Kirk Gibson, No. 12 overall
From 1981 through 1984, the Montreal Expos had three future Hall of Famers on their roster in catcher Gary Carter, left fielder Tim Raines and center fielder Andre Dawson.
Imagine adding Kirk Gibson to that lineup.
A dynamic power-speed threat in his prime, Gibson posted five straight 20-20 seasons from 1984 through 1988, and he took home AL MVP honors during the 1988 season.
He would have slotted nicely in right field to form one of the greatest outfields in MLB history.
Instead, the Expos went with Chipola College shortstop Glen Franklin, who wound up being one of six straight picks from No. 6 to No. 11 overall in the 1978 draft who failed to reach the majors.
All stats, WAR totals and draft information courtesy of Baseball Reference unless otherwise noted.