Often lost in any professional draft is that it’s fundamentally an achievement. For many fortunate enough athletes, the pinnacle of a successful amateur career comes in being chosen to join a big league organization. From the team and fan perspective, however, it’s another story on draft night. It quickly becomes less an end than a beginning, a pressure-filled exercise of identifying and selecting a collection of talent primed to make an impact at the big league level. That same duality exists even after the picks are made, wherein some players are just happy to receive a major league contract while other negotiations are contentious and can result in a lost pick.
With the nature of the MLB Amateur Draft, the vast majority of those lost picks don’t exactly come back to haunt the teams that make them. Studies have shown that players taken outside of the first round are statistically more likely to miss out on reaching the majors than getting there. On the other hand, the only thing worse than letting a future star slip through your grasp on draft night is to draft that caliber of player, only for them to go on to success elsewhere. And no, that scenario isn’t that rare.
Since 2012, teams have had just about six weeks to get their draft picks signed, leaving a pretty short window to negotiate with those looking for a signing bonus larger than their draft slot would dictate. Then you also have to contend with players balancing a shot at pro ball with other options, typically a college scholarship offer. Through these and other situations, you can build more than one impressive, Hall of Famer-laden roster out of players who couldn’t (or wouldn’t) come to terms with the organization that drafted them before ascending to stardom somewhere else.
20 Chris Sale - Colorado Rockies
Turning down $100,000 may not often be the smartest path to choose, but it worked out awfully well for ace lefty Chris Sale. That was the amount that the then-high schooler passed on as a signing bonus from the Rockies, who initially drafted him in the 21st round of the 2007 MLB Amateur Draft. Sale went to Florida Gulf Coast University, where he developed into a Collegiate Baseball Player of the Year and turning himself into a first round pick.
In doing so, he also carved out a connection with the FGC Eagles, one that has seen him return to campus regularly to work out with the team or just be around his old coaches. Now that he's a seven-time All-Star set to make $15 million this season, Sale probably isn't regretting the $100,000 he gave up.
19 Kyler Murray - Oakland Athletics
Granted, it's hardly a perfect fit to include Kyler Murray here. The two-sport phenom has, for one, already signed a contract with the Oakland A's, one that preceded his Heisman trophy-winning NCAA Football season that has put him in the conversation to be among the top picks of the NFL Draft (he went ninth overall in last year's MLB Draft). Moreover, Murray still has a ways to go before reaching the majors, even if that's the direction he chooses.
Nevertheless, it'll be a fascinating journey to see where this goes, as Oakland and Major League Baseball have apparently taken dramatic steps to keep the Oklahoma Sooners quarterback in baseball as his draft stock rises and he's announced his declaration for the NFL Draft.
18 Ian Kinsler - Arizona Diamondbacks
Apparently the Arizona Diamondbacks wanted Ian Kinsler. Like, really wanted him. The D-Backs drafted the Tucson native and local high school star on two separate occasions - in the 29th round in 2000 and again in the 26th round in 2001 - only to get rebuffed each time as the second baseman enrolled at the University of Missouri.
As such, it probably didn't surprise Arizona greatly to see Kinsler go onto make five All-Star teams and win two Gold Glove awards. It's a bit curious, then, that the 36-year-old has now played for four different organizations across 13 seasons, and the Diamondbacks haven't made an evident play for him as a major leaguer.
17 Tim Lincecum - Chicago Cubs
At 5'11" and a flimsy 170 pounds, Tim Lincecum always knew that he was more than his stature would suggest. Lincecum was drafted twice - first in the 48th round of the 2003 draft by the Chicago Cubs and then in the 42nd round of the 2005 draft by Cleveland. However, the heat-throwing righty opted to pass on both opportunities, electing instead to bet on himself at the University of Washington.
That bet paid off in a big way, as an incredible season with the Huskies earned Lincecum the 2006 Golden Spikes Award and a move all the way up to 10th overall in the 2006 draft, where he was taken by the San Francisco Giants. After two Cy Young awards and three World Series championships, it's amazing to think that the diminutive flamethrower may have never gotten a chance in the majors.
16 George Springer - Minnesota Twins
The 2017 MLB season was an encouraging one for the Minnesota Twins, who earned their first postseason berth in eight years - if you can even call a loss in the AL wild card game a 'postseason berth'. It was also a good year to be the Houston Astros, who broke through to win the World Series on the backs of some young, homegrown talent. A big part of that group was All-Star outfielder George Springer, who would win a Silver Slugger award that year along the way to World Series MVP honors. It was surely bittersweet for the Twins' to watch Springer's rise, having drafted him back in 2008 only to see him join the University of Connecticut instead.
15 Jake Arrieta - Cincinnati Reds
The owners of the National League's second-worst team ERA in 2018, the Reds have understandably taken aim at improving their rotation ahead of 2019. The additions of Alex Wood and Tanner Roark represent steps in the right direction, but aren't likely to blow anyone away. But you know who would help as an upgrade for Cincy's hurlers? Cy Young award winner and World Series champion Jake Arrieta, who was first drafted by the Reds in the 31st round of the 2004 MLB Draft.
To be fair, the bearded right-hander started his career in the majors by stumbling through a stint in Baltimore, so who's to say he would've fared any better in Cincinnati. Still, Arrieta's no-hitter against the Reds had to sting a little extra knowing he was once their property.
14 Ozzie Smith - Detroit Tigers
There are 25 shortstops enshrined in Cooperstown. Yes, in the history of the game, just 25 players at the position have been deemed Hall worthy. Incredibly, the Tigers selected two of those men as part of the same draft class. But before 1976 draftees Alan Trammell and Ozzie Smith had the chance to engage in a position battle for the ages, the “Wizard of Oz” rebuffed the Tigers’ efforts to get his name on a contract.
Detroit was hardly in position to rue the loss of their seventh round pick, given the arrival of Trammell. However, in comparing the two Hall of Famers, Smith’s 15 All-Star appearances and 13 Gold Gloves loom large over Trammell’s six and four, respectively. It’s also worth noting that the long-time Cardinals whiz reached Cooperstown a full 16 years before the 1984 World Series MVP, despite the two retiring the same year.
13 Gerrit Cole - New York Yankees
When you’re the New York Yankees, you probably don’t hear ‘no’ very often. And so it almost seemed too easy when Gerrit Cole fell into their laps late in the first round of the 2008 draft amid sign-ability concerns. For the Bronx Bombers, the allure of pinstripes coupled with Cole’s childhood Yankee fandom set the stage for a smooth negotiation. However, Cole’s parents were determined to see their son get an education, and so they remained steadfast in their insistence that the two-time All-Star accept a scholarship offer to attend UCLA.
The powerful right-hander would ultimately go first overall to the Pirates and net a signing bonus more than double than what the Yankees had offered three years earlier. Since then, Cole has garnered two All-Star nods and two top five Cy Young finishes, all the while looking like a front line starter that the Yanks could sure use.
12 Buster Posey - Los Angeles Angels
There were a total of 1,501 players selected in the 2005 MLB Draft. Those left waiting to hear their names called until the very end are mostly unfamiliar to baseball fans, having never had a sniff of the big leagues. albeit with one notable exception. Buster Posey, then a high school pitcher considering enrolling at Florida State University, was taken by the Los Angeles Angels with the 1,496th selection of the draft. Posey, of course, would attend FSU, convert to shortstop and then to catcher and ultimately serve as the foundation to three World Series championships for the San Francisco Giants, an in-state, National League rival of the Angels.
11 Todd Helton - San Diego Padres
Back in 1994, Todd Helton was a two-sport star at the University of Tennessee, starring as a slugger and relief pitcher for the Volunteers while also quarterbacking the Vols' football team - that is, until an injury opened the door for his backup, Peyton Manning. Manning ultimately set school records en route to becoming one of the greatest quarterbacks of all-time and Helton pursued baseball, making five All-Star teams and crafting a Hall-caliber career with the Rockies.
Had Helton signed after being drafted by the San Diego Padres out of high school in the second round of the 1992 draft, he likely would have never played QB at Tennessee, never began a lifelong friendship with Manning and probably never pieced together such impressive offensive numbers without the benefit of playing home games at Mile High Coors Field.
10 Aaron Judge - Oakland Athletics
A larger-than-life slugger with a knack for long bombs and a readily-marketable name that has already spawned a catchphrase ("All Rise!"), Aaron Judge seems like he was destined to be a Yankee. However, the sight of Judge in pinstripes almost never happened. The 26-year-old rightfielder was first drafted by the Oakland A's, whose Oakland Coliseum is located just 80 miles from the big man's hometown of Linden, CA. While Judge acknowledged that playing close to home was "tempting", he ultimately elected to accept a scholarship offer to Fresno State instead, filling out his 6'7" frame and transforming himself from a 31st to a 1st round pick in three years.
9 Paul Molitor - St. Louis Cardinals
If reports are true, then it was a measly $4,000 that kept the Cardinals from getting themselves a future Hall of Famer and the 10th-ranked player on baseball's all-time hits list. When the Cardinals drafted high school infielder Paul Molitor in the 28th round of the 1974 draft, they offered him $4,000 to sign. He wanted $8,000, at which point St. Louis promptly walked away, leaving Molitor to enroll at the University of Minnesota and put together a collegiate career that launched him up to the No. 3 overall pick three years later. That would bring him to Milwaukee, and the rest is history.
Molitor spent 15 of his 21 seasons as a member of the Brew Crew, compiling 3,319 hits, seven All-Star selections, four Silver Sluggers and even a World Series MVP trophy as a member of the 1993 Blue Jays before turning to a successful managerial career.
8 Barry Bonds - San Francisco Giants
The story of Barry Bonds' original draft selection is less a story of 'what if' and more another light shed on how the home run king isn't exactly the greatest of guys. A missed opportunity to sign Bonds should rank higher than this, were it not the Giants eventually becoming his primary MLB home. However, many forget the Giants drafted and failed to sign him in 1982.
It's a telling sign of Bonds' character, however, that he elected to attend Arizona State rather than sign with the franchise for whom his dad starred in the 1970s because - get this - they offered him $70,000 and he wanted $75,000. Things would ultimately work out just fine for all parties involved: the Pirates drafted Bonds in 1985 and saw him earn two NL MVP awards while in Pitt, the Giants signed him in 1992 and got five MVP trophies and the vast majority of those 762 home runs and Bonds simply raked wherever he went.
7 Kris Bryant - Toronto Blue Jays
The 2010 draft was the first in which long-time Blue Jays executive Alex Anthopoulos officially took the helm as GM - and the change was noticeable instantly. Anthopoulos introduced a brazen new draft strategy of embracing high-upside players who fall on account of sign-ability concerns. This approached helped Toronto land Aaron Sanchez and Noah Syndergaard in that draft, along with players like Marcus Stroman in future years. But perhaps the Jays' biggest risk was one that ultimately didn't pay off: an 18th round flyer on Kris Bryant in 2010.
Strangely, Bryant recalls that the club "didn't really offer anything" before letting the future MVP, Rookie of the Year and World Series champion enroll at the University of San Diego. Truly an opportunity wasted.
6 Mark McGwire - Montreal Expos
Could one unsigned draft pick really change the fate of an entire franchise? We will never know whether the presence of Mark McGwire may have saved baseball in Montreal, but it sure did come close to happening. The Expos drafted Big Mac with their eighth round pick of the 1981 draft and offered him $8,500 to forego a scholarship at USC. McGwire would decline the contract offer and join the Trojans, who already had Randy Johnson and Jack Del Rio, before being a part of the silver medal-winning U.S. team at the 1984 Olympics. All that would lead to him being drafted by the Athletics and becoming one of the game's preeminent home run hitters.
5 Max Scherzer - St. Louis Cardinals
What do the Cardinals, Diamondbacks and Tigers all have in common? Each organization can lament losing out on Max Scherzer, current ace of the Nationals and possibly the best pitcher in baseball. But while Arizona at least turned a young Scherzer into serviceable starters Ian Kennedy and Edwin Jackson and the Tigers got a Cy Young and a trip to the World Series before losing him to free agency, the Cardinals got nothing. They drafted the local high school star in the 43rd round of the 2003 draft, only to see Scherzer head two hours west to the University of Missouri. Maybe St. Louis never had a realistic shot at getting him under contract, but his three Cy Youngs, the most of any active pitcher, have to sting for a franchise that has had just one Cy winner (Chris Carpenter in 2005) since 1970.
4 Roger Clemens - New York Mets
You can argue Steve Phillips's track record as an executive for the New York Mets. He did, however, apparently have an unfortunate role to play in New York's inability to come to terms with their 12th round pick from that same draft, Roger Clemens. The club and the Rocket were $10,000 apart in contract negotiations, which would have hardly been a stumbling block had the Mets actually seen Clemens pitch. But all three of scouting director Joe McIlvaine's trips to the fireballer's San Jacinto Junior College resulted in rain outs.
So the $10,000 that Clemens wanted wound up earmarked for Phillips, and the rest is history. Now, the most common association we have between the seven-time Cy Young and the Mets is Clemens throwing a broken bat in the direction of Mike Piazza during the 2000 Subway Series.
3 J.D. Drew - Philadelphia Phillies
Based on resume alone, J.D. Drew does not belong near the top of this list. But the ill-will and antipathy that came out of what was probably the most bitter, contentious contract negotiations in big league history make this selection worthy of its lofty rank. Drew, and agent Scott Boras, was adamant about getting what would've been an unprecedented $10 million signing bonus after the first 30-30 season in college baseball history at Florida State. The Phillies had no intention of paying $10 million, but took him second overall anyway.
Not only did Drew refuse to sign, but became embroiled in some mud-slinging with the organization while arguing that he should be granted free agency. The outfielder would be drafted and signed by the Cardinals one year later in 1998, but Phillies fans never forgot his demands. They relentlessly threw debris at him during his first game in Philadelphia to the point that play needed to be briefly suspended and would carry that grudge throughout his 14-year career.
2 Randy Johnson - Atlanta Braves
To this day, baseball fans still talk in revered tones about the incredible Atlanta Braves rotation of Greg Maddux, Tom Glavine, John Smoltz and Steve Avery that sparked five World Series appearances between 1991 and 1999. Now, imagine if it was better. Had the Braves come to terms with 1982 fourth round pick Randy Johnson rather than watch him go pitch at USC, Atlanta's rotation might well have added one more Hall of Famer and five more Cy Young awards to a group that already boasted three and seven, respectively.
Not that the club needed much more pitching help, but maybe that would have assured the Braves of more than one World Series championship over that dominant stretch. Ironically, Will Clark was selected by the Kansas City Royals one pick after the Big Unit that year, but he also declined a big league contract in favor of a college career.
1 Tom Seaver - Dodgers & Braves
For Tom Seaver, it seems like pitching in the majors was never the challenge that actually getting there was. It was one thing when the Los Angeles Dodgers, reportedly at the urging of scout Tommy Lasorda, refused to give in to Seaver's demands of a $70,000 signing bonus upon taking the right-hander in the 10th round of the 1965 draft. But the debacle of 1966 was another matter, entirely, as he was taken 20th overall by the Braves and signed soon thereafter.
However, then-Commissioner William Eckert voided the contract upon discovering that Seaver's USC Trojans had played two exhibition games that year. He appealed, and was granted the right for any other team to match the Braves' contract offer, which the Mets gladly did. One year later, he won Rookie of the Year honors to launch a Hall of Fame career that would span 20 seasons and would include 311 wins, three Cy Young awards and a World Series ring.