As the 2010 Draft approached, the top of the first round took shape. A big three had separated itself from the rest of the pack: Bryce Harper, Jameson Taillon and Manny Machado.
It was fairly evident Harper would go No. 1 overall to the Nationals, and that Taillon and Machado would be taken second and third, though the order wasn't clear. The Pirates took Taillon at No. 2 and the Orioles nabbed Machado, who is one of four players taken in the top 13 picks of that Draft who are now playing for a World Series ring, though none for the team that drafted him that June.
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The player from the 2010 class with the highest career Wins Above Replacement to date is also the one taken last among that quartet: Red Sox Game 1 starter Chris Sale. Hindsight is always 20-20 when it comes to amateur scouting, and there are several teams that picked between the Orioles at No. 3 and White Sox at No. 13 that wish they could get another shot.
That run of picks has greatly impacted this year's World Series. In between Machado and Sale, Red Sox reliever Drew Pomeranz and Dodgers catcher Yasmani Grandal were selected, Pomeranz at No. 5 overall by the Indians, and Grandal at No. 12 by the Reds. MLB Pipeline talked to three of the scouting directors who were responsible for making those selections and discussed what they saw then in the players who are vying for a World Series title now.
Machado stands out
While Harper was the easy frontrunner to go at No. 1, Machado wasn't that far behind. A lanky, athletic shortstop from the Miami high school ranks, he drew comparisons to Alex Rodriguez. MLB Network analyst Harold Reynolds stated before the Draft that he'd take Machado No. 1 if it were his pick to make. The Nationals, Pirates and Orioles had all scouted him heavily on the summer showcase circuit and throughout his senior year.
"We got word pretty early Bryce was going to go No. 1," said Joe Jordan, the Orioles' scouting director at the time. "We were waiting on Pittsburgh to decide. Our room liked both guys, and we knew we'd get a good player. We were happy the way it worked out.
"Manny was under consideration going into the spring based on his summer and all the work we'd done. We had gotten so many looks and by the end of the spring, we were in good shape."

Machado certainly paid early dividends, making it to the big leagues just more than two years after being drafted, at age 20, months after Harper debuted, and learned to play third base on the fly upon his arrival. Since his debut, Machado has made four All-Star teams, is second among 2010 first-rounders in WAR (33.8), made a seamless transition back to shortstop while being the hottest commodity on the trade market this summer and is due for a very large payday on the free-agent market this offseason.
Sale slides in the Draft
Picking at No. 13, then-White Sox scouting director Doug Laumann knew Machado was never going to get to them, though he knew him well thanks to longtime South Florida scout Jose "PePe" Ortega. Laumann also thought there was no chance that Sale, coming off of a dominant season at Florida Gulf Coast University, would be in the mix, either.
"There were a couple of teams we thought had him targeted," Laumann said. "Once he started getting past those teams, we had a good relationship with the guys who represent Chris, they were keeping in touch and letting us know he might get to us. We were amazed by that, but we had to be ready. As each pick went by, it became apparent it was going to happen."

The only team possibly standing in the way was the Reds, picking just ahead of the White Sox at No. 12. This was not an unfamiliar scenario for the two teams. In 2008, the Reds picked seventh and the White Sox picked eighth. Cincinnati had Yonder Alonso and James Beckham atop its board, and scouting director Chris Buckley went with Alonso. The White Sox took Beckham. A similar situation was brewing two years later as Sale slid out of the top 10.
"It came down to Yasmani Grandal and Sale," said Buckley, echoing the top two for Laumann at the time. "I felt a little more comfortable with Grandal. He was a switch-hitting catcher with power and a good body. I should've picked Sale."
Grandal has become a solid big leaguer (postseason defensive struggles aside) and is playing for a World Series championship with the Dodgers alongside Machado. But he stands fifth in WAR among 2010 first-rounders, behind Sale, Machado, Harper and Christian Yelich, the No. 23 pick (by the Marlins) that year.

"If I could go back in time, we'd be happy taking Chris," Buckley said. "It just doesn't work that way. But Yasmani has turned out to be a really fine player. We're happy for him. We're hoping he gets a championship ring. Anybody who's been a scouting director would like some do-overs. I don't need a do-over, because he's a good player, but obviously Chris has been outstanding."
Bad delivery, lack of physicality
That left Sale for the White Sox to take. But why did the left-hander not go as high as expected, and how did Chicago end up feeling comfortable taking him? It took some conviction and a little bit of good fortune.
Based on his performance, most felt Sale would be the first college pitcher taken that June, perhaps in the top five. Laumann had heard some rumblings about the Royals selecting him at No. 4. In the end, it was questions about his frame and his arm action that had several teams deciding to pass.
"People got on his delivery, his upside down elbow," Buckley said. "He was a tall, thin kid. Us veteran guys, we've given some on pitching when you see guys like Sale or Jacob Arrieta, who we didn't necessarily believe had a starter's delivery. Everyone liked Chris Sale. He had good stuff, he competed really well. But his delivery was a little different, and that's why he moved down a little."
"We had guys who thought he fit top five," Jordan said. "He was behind the first three. But looking back and being totally honest, there are certain guys that go against the traditional mold, if you will. We're evaluating deliveries and arm action more than ever. It may have hurt him more now than it did then. That was part of our discussion, no question."
Sale's arm action and the lack of physicality made teams worry that he would either break down or profile best as a reliever. So down he slid, and Thomas Pomeranz, who was added to the Red Sox's World Series roster this year just before it began, ended up being the top college pitcher taken, by the Indians at No. 5. Three other college arms went before Sale did, with the D-backs taking Barret Loux out of Texas A&M at No. 6, the Mets going with North Carolina's Matt Harvey at No. 7 and the Blue Jays selecting Georgia Tech ace William McGuire at No. 11.
Sale was not the typical White Sox selection in those days. Chicago liked big, physical pitchers and athletes in the field. Had the lefty gone before the White Sox pick, and Grandal been gone, they were talking about Arkansas infielder Zack Cox as a safe college performer, fellow Razorback Brett Eibner as an intriguing two-way player with a strong arm on the mound and athleticism in the outfield and prep right-hander Mike Foltynewicz, though they had been burned by high school pitching in the past. Taking Sale would be a departure.
Good fortune comes into play in three different ways
Because the White Sox didn't think Sale would be in play, they didn't spend hours breaking down his mechanics. Kenny Williams, Chicago's general manager at the time, liked to go out and see potential first-round picks, and he hadn't even seen Sale pitch.
"We had to fill him in and everyone else in about what he was, what he could do," Laumann said. "Not everyone had seen him. Sometimes you overanalyze stuff. Who's to say if we had beat our heads against the wall and gotten into a lengthy discussion that I wouldn't have been swayed to go in another direction."
Good fortune also came into play as the top 10 unfolded. The White Sox Draft room was situated just above the left-field bullpen in Chicago. A pair of left-handers on the big league staff were throwing bullpens as it became more and more clear Sale had a chance to get there. Williams turned to Laumann and asked him if Sale could help the big league club by September. The veteran scouting director answered "yes" without hesitating. When Williams asked Laumann how he could be so sure, the answer was simple.
"I looked down at the guys throwing their bullpens and said, 'Because he's better than the two guys throwing down there right now,'" Laumann said.
How Laumann could be so sure when others in the industry had questions about Sale brings us to Chicago's final stroke of luck: Laumann had seen Sale at his absolute best that spring.
Laumann remembered the date immediately: April 23. Sale won a 1-0 pitchers' duel against Belmont with a complete game. The lefty struck out 15 and walked one. But it was more than just those numbers that made Laumann bypass conventional wisdom.
"He was 93-94 mph in the first three innings and 94-96 mph in the middle three," Laumann recalled. "His team scored a run in the seventh, and he was 97-98 mph in the seventh through ninth, all the way through pitches 130, 131 and 132. The questions about strength and stamina, all that went out the window for me. I didn't care about some of those things, because the stuff was so dynamic, and in my mind, he was a starter."
Laumann was reminded by Buckley, the director who passed on Sale one pick ahead of him, that that's the only difference between the two of them as scouting directors. In fact, it might be the only thing that separates veteran scouting executives.
"He said, 'The only difference between me and you?'" Laumann said. "'It's all about the day you saw him.' We want to go on our background, the information we've gathered, the tools. But you have to see a guy pretty good to put your neck out on the line for him."