The 2026 Major League Baseball draft is coming up on July 11, and there is no obvious choice for the Chicago White Sox, who have the No. 1 pick. It might be UCLA shortstop Roch Cholowsky, Georgia Tech catcher Vahn Lackey or maybe Texas high school shortstop Grady Emerson.
Often, the top choice is clear -- think Stephen Strasburg in 2009 or Bryce Harper in 2010. Sometimes it's more muddled with multiple players, like it is this year, while sometimes it's just a weak draft in general. But in some years, there's a healthy debate and the team drafting first must decide between two -- or more -- players with top-pick talent.
Throughout history, there have been a number of such debates. Let's dive into some of the best of all time as we wait to see what decision Chicago makes this year.
(To be clear: We're considering if there was a debate at the time and excluding whether the top pick proved worthy of the selection in the long run.)
2023, Pittsburgh Pirates: Paul Skenes vs. Dylan Crews
It's easy to forget given Skenes' instant stardom and Cy Young trophy in 2025, but this was one of the best draft debates in history as the two LSU teammates had two of the most dominant college seasons ever in leading the Tigers to a College World Series title. Indeed, the rankings were split: MLB.com went Skenes and then Crews; Baseball America went Crews and then Skenes; FanGraphs had Crews first, Wyatt Langford second and Skenes third; ESPN went Langford-Crews-Skenes. Some of that was the risk associated with drafting a pitcher, but the Pirates rolled the dice and took Skenes.
Was it the right pick? Yep. Skenes has a career 2.16 ERA as he looks on his way to becoming one of the best first overall choices of all time if he can stay healthy. The Washington Nationals took Crews with the No. 2 pick and his struggles to hit in the majors have been one of the biggest draft surprises in recent years as he looked like a sure thing coming out of college.
2022, Baltimore Orioles: Jackson Holliday vs. Druw Jones
This was a fun one, two high schoolers, both sons of longtime major league stars. Jones was viewed as a superlative center fielder like his dad, new Hall of Famer Andruw Jones, with five-tool potential. Jackson, son of seven-time All-Star Matt Holliday, hit .685 as a senior, setting a national high school record for hits in a season. Most of the predraft boards had Jones first and Holliday second, but the Orioles went with the infielder.
Was it the right pick? So far, even as Holliday is still trying to live up to the hype surrounding him after he became the No. 1 overall prospect in the game following an impressive minor league season in 2023. He's still very young, just 22 years old, but has produced higher-than-expected strikeout rates and subpar range at second base. The Arizona Diamondbacks took Jones with the second pick and he's currently in Double-A, hitting .252 with only two home runs as his power just hasn't developed.
2017, Minnesota Twins: Royce Lewis vs. Hunter Greene
Greene, who hit 102 mph pitching at Notre Dame High School in Sherman Oaks, California, was the top talent on everyone's board: ESPN, Baseball America and MLB.com all had him as No. 1 (he was a two-way star in high school, but his pro future was as a pitcher). But selecting a high school right-hander in the draft has historically been considered high-risk, and the Twins elected to go for Lewis, another Los Angeles-area high school star -- but a position player. Lewis did sign for $500,000 less than Greene, but this felt like the Twins wanting the shortstop over the pitcher. To this day, no high school right-hander has ever gone No. 1.
Was it the right pick? Not really. Lewis just hasn't been able to stay healthy, so there has been some bad luck here. He missed two crucial full minor league seasons between COVID-19 and a torn ACL, which hurt his development. He had an incredible 58-game run with the Twins in 2023 but hasn't been able to reach that level since. Greene, who went second to the Cincinnati Reds, has had his own injury issues -- including Tommy John surgery, and he's currently recovering from surgery in March to remove bone spurs -- but is neck-and-neck with Drew Rasmussen for most WAR among 2017 first-rounders.
2015, Arizona Diamondbacks: Dansby Swanson vs. Alex Bregman
This was a tale of two SEC shortstops: Vanderbilt's Swanson and LSU's Bregman. Swanson had the better glove, Bregman the better bat. Most draft boards had Swanson first and Bregman second, with prep shortstop Brendan Rodgers also in the mix. What followed was one of the strangest affairs in draft history.
Tony La Russa and Dave Stewart ran baseball operations for Arizona. They drafted Swanson, no shock there. That offseason, however, after playing just 22 games in the Diamondbacks' organization, La Russa and Stewart flipped Swanson, outfielder Ender Inciarte and pitcher Aaron Blair to the Atlanta Braves for starter Shelby Miller and relief prospect Gabe Speier. Miller was coming off a fine season for the Braves -- going 6-17 but with a 3.02 ERA and 205 innings -- but the deal was immediately panned, especially factoring in that Inciarte was coming off a 5-WAR season with Arizona. Related was another trade between the Diamondbacks and Braves during the 2015 season when the Diamondbacks traded pitcher Touki Toussaint, their first-round pick in 2014, plus injured pitcher Bronson Arroyo to Atlanta. Essentially, the Diamondbacks gave away Toussaint to dump about $10 million in Arroyo's salary.
Was it the right pick? Not the way it unfolded. Both have had excellent careers, although Bregman leads in WAR, 45.1 to 29. But the trade just makes the Swanson pick look even more misguided. Miller got hurt and won just five games in three years with Arizona. Swanson had 14.9 WAR with the Braves and helped them win a World Series, while Inciarte had 9.6 WAR in Atlanta. To make matters worse, Arizona then signed Zack Greinke to a deal that made him the highest-paid player in the game. The 2016 Diamondbacks finished 69-93 and La Russa and Stewart were replaced.
2012, Houston Astros: Carlos Correa vs. Byron Buxton
In one sense, this was just as much Buxton versus Mark Appel as it was Correa versus Buxton. Baseball America and MLB.com ranked Buxton first and Appel second (and Correa fifth) while ESPN had Buxton first and Correa second. That meant Buxton was the consensus top guy. The Astros, however, wanted to save money on the top pick and allocate those extra resources for later in the draft, so they went with Correa, who signed for $1.2 million less than Buxton.
Was it the right pick? It worked out beautifully for Houston. Correa was a centerpiece of the rebuild and has had more value in his career than Buxton -- 47.1 WAR to 32.8 WAR -- although both have been injury-prone. The Astros then used the savings to give Lance McCullers Jr. an overslot bonus with the 41st pick. Buxton went second to the Twins while concerns about Appel's signability proved true. He went to the Pirates with the eighth pick, didn't sign, and then the Astros took him first in 2013 -- over Kris Bryant. That selection was certainly a mistake, as Appel pitched just 10 innings in the majors.
2004, San Diego Padres: Matt Bush vs. Stephen Drew
This was a weird one. Florida State shortstop Drew and Long Beach State right-hander Jered Weaver were considered the top two players in the draft. The Padres appeared to be leaning toward Drew, although there were concerns about the bonus demands from both players. The Padres shifted to Bush, a two-way high school star from the San Diego area, after Bush agreed to a discounted signing bonus. Though he was a consensus top-10 talent, nobody had him at the top of their draft boards.
Was it the right pick? This goes down as one of the worst No. 1 picks ever, especially considering the guy the Detroit Tigers took with the next pick: Justin Verlander. Bush got suspended before playing a minor league game, never hit in the minors, had other incidents and eventually spent three years in prison for a DUI hit-and-run. He resurfaced as a pitcher with the Texas Rangers in 2016 and spent six seasons in the majors. Weaver fell to the Angels at No. 12, and Drew went 15th to the Diamondbacks, with Weaver producing the second-highest career WAR of the first-round picks that year and Drew the fifth highest.
2001, Minnesota Twins: Joe Mauer vs. Mark Prior
This might be the ultimate draft debate. Prior was widely regarded as the best college pitcher ever after a dominant junior season at USC in which he went 15-1 with a 1.69 ERA, 202 strikeouts and just 18 walks. Mauer was the local kid from St. Paul, Minneapolis, a gifted athlete who was the national high school football player of the year as a quarterback with a scholarship to Florida State. With Prior's bonus demands perhaps higher than the Twins were willing to pay, they selected Mauer while insisting that it had nothing to do with money.
Was it the right pick? Hard to argue otherwise. Mauer became a three-time batting champ, an AL MVP and a Hall of Famer. The Chicago Cubs took Prior with the second pick, and he looked like he was on a similar career path, finishing third in the NL Cy Young voting in 2003, before shoulder injuries ruined his career. Consider this, though: The Twins made the playoffs in 2002, 2003 and 2004. Do they win a World Series if Prior is on the roster those years?
1999, Tampa Bay Rays: Josh Hamilton vs. Josh Beckett
Well, they were technically the Devil Rays back then. But anyway, this was a choice between a high school outfielder from North Carolina and a brash-talking high school pitcher from Texas. "I think I'm the best," Beckett said at the time. "That goes along with being arrogant out there. You've got to think you're the best." He declared that he would be an All-Star within two years. It appeared that he'd be the first high school right-hander ever drafted No. 1 -- until the Rays shifted late in the process to Hamilton.
Was it the right pick? It could have been, but Hamilton experienced addiction in the minors, later surfacing with the Reds at age 26 and then winning an AL MVP award with the Rangers. Beckett wasn't an All-Star in two years, but he was in the majors -- and led the then-Florida Marlins to the 2003 World Series title with a clinching shutout in Game 6.
1997, Detroit Tigers: Matt Anderson vs. J.D. Drew
Baseball teams did a lot of dumb things in the 1990s. Drew was the clear top talent in the '97 draft after posting the first 30/30 season in NCAA history at Florida State. But a technical loophole had allowed four first-round picks from the 1996 draft to become free agents and two of them signed for $10 million, so Drew and agent Scott Boras declared Drew was worth that much as well. (Kris Benson, the top pick in the 1996 draft, had received a $2 million bonus.) The Tigers passed on Drew and took Rice reliever Anderson and his 100 mph heater.
Was it the right pick? Nope. Taking a relief pitcher first was strange enough, but Anderson battled injuries and control problems. The Tigers should have just drafted Drew and given him the $10 million. He had an excellent career with 44.9 WAR (only Lance Berkman among '97 first-rounders had more). The Philadelphia Phillies took Drew with the second pick -- and didn't sign him after a contentious negotiation. Drew went back into the '98 draft, where the St. Louis Cardinals finally signed him with the fifth selection.
1993, Seattle Mariners: Alex Rodriguez vs. Darren Dreifort
This might sound familiar. Rodriguez was a high school shortstop -- the best ever, according to most scouts, maybe even the best prospect ever. Dreifort was the cream of the crop of collegiate arms, a right-hander from Wichita State with a fastball in the upper 90s and a higher scouting grade via the Major League Scouting Bureau (71 to 69). Dreifort had pitched in relief for the Shockers (although he had pitched over 100 innings that season) and was viewed as someone who could jump straight to the majors. Still, this should have been an easy choice, except Mariners manager Lou Piniella initially pushed for Dreifort.
Was it the right choice? Common sense prevailed, and the Mariners took Rodriguez, even after he fired his first agent before the draft and hired Scott Boras. A-Rod was in the majors a year later at 18 years old. Dreifort battled injuries throughout his career, undergoing 22 different surgeries, but at least managed to parlay a 48-60 career record into $63 million in career earnings.
1990, Atlanta Braves: Chipper Jones vs. Todd Van Poppel
This is one of the most famous draft stories of all time. Van Poppel, a high school right-hander from Arlington, Texas, was viewed as perhaps the best high school right-hander of the draft era at the time, maybe the best prep pitching prospect since David Clyde 17 years prior. But Van Poppel also had a commitment to the University of Texas, and he told teams not to draft him. So, the Braves didn't, instead shifting to a high school shortstop from Florida named Chipper Jones.
Was it the right pick? Jones made the Hall of Fame after spending his entire 19-year career with the Braves. Meanwhile, the A's gambled on Van Poppel with the 14th pick and did sign him -- to a major league contract, which led to him being rushed to the majors before he was ready when he ran out of minor league options. Though Van Poppel carved out a 10-year career, he always had trouble throwing strikes and finished with a 5.58 career ERA.
1987, Seattle Mariners: Ken Griffey Jr. vs. Mike Harkey
"Has all the tools to be a superstar," wrote Mariners scout Bob Harrison of Griffey in the spring of 1987. So, this was a slam dunk then, right? Nope. Similar to Seattle's decision six years later, this should have been a no-brainer, but Mariners owner George Argyros, wanting a quick fix, pushed the club at first to draft Harkey, a right-hander from Cal State Fullerton, over a high school kid. Scouting director Roger Jongewaard and general manager Dick Balderson finally convinced Argyros that Griffey had to be the choice.
Was it the right pick? Umm ... yes. Harkey went fourth to the Cubs and reached the majors quickly in 1988 but would win just 36 games over an eight-year career. Griffey ... well, we all know what the 13-time All-Star and Hall of Famer went on to do -- and meant to the city of Seattle.
1985, Milwaukee Brewers: B.J. Surhoff vs. Will Clark
The first round of the 1985 draft still rates as the best ever: In just the first six picks, you had Surhoff (34.4 WAR), Clark (56.5), Bobby Witt (142 wins), Barry Larkin (Hall of Famer) and Barry Bonds (all-time home run leader). The college game had fully matured by the mid-'80s, and all five were college stars. Later picks in the first round included Rafael Palmeiro, Gregg Jefferies, Walt Weiss, Pete Incaviglia, Brian McRae, Joey Cora and Joe Magrane. Anyway, the Brewers settled on North Carolina catcher Surhoff, who had also played some shortstop, over power-hitting Mississippi State first baseman Clark, believing Surhoff's all-around game made him the best talent.
Was it the right pick? It's hard to knock a pick who ended up with over 2,300 career hits, but given that Clark, Larkin and Bonds went right after, the Brewers missed on drafting a franchise player. Developing Surhoff as a catcher might also have been a mistake, as he hit better after leaving Milwaukee and moving to the outfield.
1981, Seattle Mariners: Mike Moore vs. Ron Darling
For the second time in three years, the Mariners had the first pick -- anyone remember Al "Choo Choo" Chambers? -- and they were determined to take a pitcher. They had settled on Oral Roberts right-hander Moore. That is, until Darling pitched a masterful NCAA playoff game, taking a no-hitter into the 12th inning before losing 1-0. At that point, the Mariners had a tougher choice. Then, Darling hired an agent. That was enough to scare off the penny-pinching Mariners.
Was it the right pick? Call it a coin flip. Moore went 161-176 with 27.9 WAR (winning a World Series with the A's) while Darling finished 136-116 with 19.6 WAR (winning a World Series with the New York Mets after they acquired him from the Rangers).
1978, Atlanta Braves: Bob Horner vs. Kirk Gibson
Horner was the star slugger for Arizona State, coming off NCAA single-season and career home run records, but the Braves really wanted Gibson -- a football and baseball star at Michigan State. The problem: Gibson wanted to play his senior year of football and was a possible first-round NFL pick as a wide receiver, so the Braves weren't sure they could sign him -- or whether Gibson was fully committed to baseball. They took Horner, who went straight to the majors and won National League Rookie of the Year after hitting 23 home runs in 89 games.
Was it the right pick? Yes and no. Gibson had the better MLB career after his home-state Tigers drafted him with the 12th pick and signed him to a $150,000 bonus commensurate with Horner's, but it's likely Gibson wouldn't have signed with the Braves. The Tigers had a secret workout with Gibson at Tiger Stadium just before the draft, where Gibson launched ball after ball into the upper deck, and then told team executives, "I will play baseball, but only for the Detroit Tigers." Horner hit 215 home runs for the Braves but was out of the majors by age 31.
1977, Chicago White Sox: Harold Baines vs. Bill Gullickson
Gullickson, a hard-throwing right-hander from nearby Joliet, Illinois, was viewed as the clear top talent in the 1977 draft, but White Sox owner Bill Veeck threw a surprise curveball, drafting Baines, a Maryland high schooler he had first seen play at 12 years old. Baines was rated No. 5 by the Major League Scouting Bureau, so it wasn't necessarily a huge reach, but it might have been motivated more by money than talent. Baines signed for $32,000, the lowest of any player in the first half of the first round, while Gullickson signed for $75,000.
Was it the right pick? Turns out, it was. Gullickson had an excellent career, winning 162 games, but Baines justified Veeck's belief in him, hitting 384 home runs, driving in 1,628 runs and making the Hall of Fame.
1973, Texas Rangers: David Clyde vs. Dave Winfield
Clyde was a schoolboy legend from Houston, where he threw five consecutive shutouts in the Texas 5-A state playoffs, including three no-hitters, drawing comparisons to Sandy Koufax and receiving a profile in Sports Illustrated. Winfield, a two-way star at the University of Minnesota, was MVP of the College World Series even though the Gophers didn't reach the championship game. The Rangers, drawing lackluster crowds, couldn't help but select the home-state hero Clyde, making the lefty the only high school pitcher drafted No. 1 until the New York Yankees selected Brien Taylor in 1991.
Was it the right pick? No, but this is one of those great "what-ifs." The Rangers had Clyde make his professional debut in the majors, with a plan to then send him to the minors. They ended up keeping him there the rest of the season, where he made 18 starts and pitched 93 innings -- on top of the 148 innings he had pitched that high school season. His career never took off. Winfield went No. 4 to the Padres, who also sent him straight to the majors -- and on the way to the Hall of Fame.
1966, New York Mets: Steve Chilcott vs. Reggie Jackson
This has gone down as one of the biggest gaffes in draft history: The Mets taking a high school catcher who never reached the majors over the Hall of Fame legend. At draft time, Chilcott and Jackson had separated themselves as the top two talents. Jackson, an outfielder at Arizona State, believed he was going to be the top pick.
The Mets said that drafting Chilcott was about positional need, while Jackson alleges there was a racial aspect in play in his 2014 autobiography, "Becoming Mr. October." Jackson added that Bob Scheffing, then the Mets' player of development, later denied any racial aspect to the selection and blamed Casey Stengel for the choice. There might be some truth to that as well, as Stengel, who had retired as Mets manager, personally scouted Chilcott and said, "One look is enough for me."
Was it the right pick? Jackson's story aside, there was also a bias in favor of high school kids over college players in the early years of the draft (which began in 1965). Old-school baseball guys believed they could draft raw 17- or 18-year-old kids and mold them like putty into ballplayers. Go through the first decade or so of the draft and there is a long list of high school players -- and catchers, in particular -- who never made it in the big leagues. In the minors, Chilcott hurt his shoulder diving into second base in 1967 and never fully recovered, suffering constant shoulder dislocations and retiring after 1972.