Jon Lester has no business being a member of the Boston Red Sox. In retrospect, the idea that he remained available in the second round, at the No. 57 pick in the 2002 draft, is preposterous.
Eight years after the fact, it would be hard to find more than a half-dozen players from that draft who have delivered the kind of impact that Lester has provided for the Red Sox. Already, the 26-year-old left-hander has etched a place as one of the best pitchers in the game, and one of the best southpaws in franchise history.
On Thursday night in Chicago, Lester (19-8) will attempt to become the first Red Sox left-hander in almost 60 years to win 20 games. Already, he owns the team record for most strikeouts by a lefty. He is one of just six Sox lefties ever to record 15 or more wins three times. His ERA+ (ERA compared to league average) ranks second among Sox lefties, behind only Hall of Famer Lefty Grove.
The list of accomplishments goes on and on, with every point illustrating the same theme. Over the last three years, Lester has emerged as the most dominant Sox pitcher since Pedro Martinez. And so it is something of a head-scratcher that 56 players in the country were deemed worthy of selection in the 2002 draft before the Sox tabbed Lester.
In a year when the Sox did not have a first-round draft pick thanks to the signing of free-agent Johnny Damon, how is it that this formidable left-hander ended up in Boston?
The usual disclaimers apply. The draft is an inexact science. The challenges of player development are substantial. It takes more than a small degree of luck to identify a player – particularly a high-school pitcher – and watch him grow into a staff ace.
All of those factors are in play with Lester’s path from the Pacific Northwest to a Boston ace. Nonetheless, there are some fascinating plot twists – with pitcher and franchise alike – that made his availability to the Red Sox in the 2002 draft all the more intriguing.
A CONSENSUS FIRST-ROUNDER
Though he went to high school at Bellarmine Prep in Tacoma, an institution more known for its academics than its athletic program, Lester did not represent an example of overlooked talent. To the contrary, he helped put Bellarmine’s athletic program on the map. (Indeed, Celtics  first-rounder Avery Bradley also spent three years of his high school career at Lester’s alma mater.)
By the time 2002 arrived, scouts were drawn to see a pitcher who had shown great athleticism along with front-of-the-rotation size and stuff during his first three high school seasons. He was 6-foot-3, left-handed, demonstrated a strong delivery and smooth mechanics. He was also a tremendous athlete, who played first base and center field while batting third, and who starred in basketball and soccer.
Virtually every scout in the Northwest was aware of him entering the 2002 scouting season. Certainly, Lester was on the radar of Red Sox Northwest area scout Gary Rajsich.
“I’d seen him in the summer and fall of 2001. I saw what I needed to see, what you’re looking for in a prospect, a pitcher who had size and strength and great arm action,” said Rajsich. “There was a lot of excitement about him. He was going to be one of the top picks out of that area [in 2002] because of the year before.”
The baseball world had told Jon Lester that he was going to be a first-round draft choice. And as much as he tried to tune out such proclamations, Lester found it hard to ignore them.
“I thought there was a chance,” Lester said of his expectations about being a first rounder. “Everybody always tells you not to listen to what other people say. But when enough people tell you that you have a chance of going that high, you start believing it, especially as an 18-year-old kid.”
Entering his senior season in 2002, Lester was very much a part of the draft circuit in the Northwest. He met with scouts from many teams, and in January, he – along with four or five other players – took part in a private workout that was organized by Marlins Northwest area scout John Booher and West Coast cross-checker Dave Finley.
Booher, as the area scout, was long familiar with the pitcher’s body of work. He raved about Lester’s makeup and talent.
Finley had already seen Lester on the mound the previous summer and fall. After seeing him work out as a hitter and outfielder, the cross-checker became immediately sold on the pitcher’s athleticism and projectable pitcher’s frame.
“He was on my radar to be one of the first guys to see that spring,” recalled Finley.
Finley and Booher already saw Lester as a potential early pick in the 2002 draft, and worthy of further scouting attention for their Marlins franchise. But their tenure as members of the Marlins was about to come to an end.
A GAME OF MUSICAL FRANCHISES
That January, Major League Baseball was amidst a wheel play without precedent. The Boston Red Sox had been sold by CEO John Harrington to the ownership group of John Henry, Tom Werner and Larry Lucchino. One month later, Henry sold the Marlins to Expos owner Jeffrey Loria. Montreal’s flagging franchise, meanwhile, was sold to the owners of the other 29 Major League Baseball teams.
With the ownership changes came a diaspora and reconfiguration of baseball front offices. Loria brought almost all of the Montreal front office with him to Florida, cutting loose virtually every member of the Marlins’ front office in the process.
Finley learned that he would join the ranks of the unemployed on the same day that he saw Lester pitch.
“Leaving that workout, driving back from the Tri-City to the Seattle area, I got the call that basically all the Marlins were being replaced,” recalled Finley. “The Expos were coming in and we were basically all out of a job, but John Henry was our owner and he was taking care of our contract and our medical. I think I had, most of us had two-year contracts. It was kind of like, ‘We’ll get other jobs and we’re still getting paid. It’s not that bad.’”
Some Marlins executives retired or quit the industry. Booher, for instance, became an independent league coach for a year (before being hired as an area scout by the Sox for the 2003 season).
But most found jobs elsewhere, including several members of the Marlins’ scouting department who were among the first Red Sox hires by Henry’s ownership group when it took over at the start of March 2002.
David Chadd, who had been in charge of the Marlins draft under Henry, assumed the same post with the Sox. Ray Crone was retained as the national cross-checker. Finley, considered a top evaluator, was also one of the first hires, brought on to serve as the West Coast cross-checker, the same role he’d occupied for Florida. A few weeks later, near the end of March, Theo Epstein was brought over from San Diego to serve as an Assistant GM, with significant input in the draft.
By the time the hires were made, the Sox didn’t have time to concern themselves with a philosophy or methodology of draft preparation – typically considerations for winter meetings that set the stage for scouting meetings. They needed to blend front-office voices coming from different organizations and, perhaps most importantly, get out and scout.
“I don’t think we were hamstrung. [But] we weren’t really as good as we are now,” acknowledged Finley, now a Red Sox Special Assistant to the GM. “In 2002, we didn’t really have a plan or a philosophy. We would just take the best player available.”
With little time to waste in the scouting process, the new Sox evaluators deployed quickly to figure out who those “best players available” were. And so, instead of evaluating Lester for the Marlins, Finley went to Bellarmine to take a look at Lester for the Red Sox.
A TIMELY SLUMP
One dead-arm stretch changed the course of Lester’s career.
It did not come at the start of the 2002 season, however. Lester took the mound in mid-March, and Finley made a point of being there for each of the left-hander’s first two outings.
The results were impressive. Too impressive.
“His first outing he went three innings. His second outing went four innings. I never saw him pitch from the stretch. He didn’t give up anything,” said Finley. “That was the only negative. He was dominant – a dominant, dominant pitcher.”
Everything was there. Finley clocked Lester at 89-93 mph, and projected the left-hander to grow into more velocity. Coupled with the movement on that pitch, it was a potentially elite offering.
Finley also saw an ability to cut the fastball – though nothing like the hell-on-hitters offering that it Lester’s cutter has become – a solid changeup that he could throw for strikes, and a functional curve (characterized by Lester as a “slurvy” offering) that projected to be big league average.
The Sox’ West Coast cross-checker immediately concluded that the left-hander was a first-rounder. No question. But the Sox had sacrificed their first-round pick (No. 16 overall – a choice that eventually became Nick Swisher) to the Athletics as compensation for signing free-agent Johnny Damon to a four-year, $32 million deal.
The Sox’ first selection would not come until the middle of the second round, with the No. 57 overall pick. And so, Finley concluded, the Sox didn’t send a troupe of front-office members into Tacoma.
“I told David Chadd, our scouting director, there’s no way he’s getting to us. Don’t even bother seeing him,” said Finley. “He’s not going to be around.”
Indeed, Lester's performances were little short of dazzling. That year featured four West Coast high school left-handers who would go near the top of the draft: Adam Loewen (No. 4 overall, Orioles), Jeff Francis (No. 9, Rockies), Cole Hamels (No. 17, Phillies) and Lester.
Based on the two outings that he saw, as well as Rajsich’s strong reports, Finley had Lester at the top of that list. He was nothing more than a pipe dream for the Sox.
But Rajsich – who estimates that he saw Lester pitch eight to 10 times – continued to monitor Lester’s outings. He had taken to heart the advice of Chadd’s predecessor, Wayne Britton, who had told him to “keep your hand on your horses,” and to continue to follow the top players in case they slipped for one reason or another.
And after those initially dominant outings, in which Lester – who had, for the first time, not played basketball over the winter in order to concentrate on baseball – had the best velocity of his career, the slip happened.
“I think I had a pretty good year, but I don’t think it was as good as the previous three,” Lester recalled. “About halfway through the season, my velocity went down and I went through kind of a dead-arm period. It kind of scared some people away.”
A couple months into the season, Lester’s fastball was registering at 82-87 mph. His slump coincided with a visit from the Major League Scouting Bureau, which took video of him on a day when his stuff was flat, and Lester topped out at 88 mph.
“So all of a sudden,” recalled Finley, “we’re thinking at that point, he’s not throwing that well and the video isn’t that good. Maybe this guy will slide.”
Indeed, other teams were peeling off of the left-hander as a consideration for a top pick.
“People got a little bit frustrated with him, that he didn’t come as fast as they expected him to,” said Rajsich. “Because of that, I think they turned their attention elsewhere.”
Some assumed that he was dealing with physical issues. At least one American League area scout started wondering about the pitcher’s makeup, both due to his performance dip amidst the scrutiny of scouts and because of the evident frustration that he would sometimes display on the mound.
Both Rajsich and Finley considered such concerns ill-founded. Cold-weather pitchers, both noted, often go through dead-arm periods. Moreover, because Lester was not just pitching but also playing outfield, regularly taking infield and hitting, the idea of a velocity dip seemed utterly unsurprising.
As for makeup, the two had even fewer reservations. Rajsich describes Lester as one of the two top makeup guys (along with former Sox pick Chris Reitsma) he even scouted as an amateur.
“He gave you square answers, he looked you straight in the eye and he was unwavering,” said Rajsich. “He was very confident.”
And so, the Sox felt that a door to opportunity might be cracking open. That notion was reinforced towards the end of the year, when Lester’s velocity started to pick back up, but the number of scouts following him remained somewhat diminished.
Finley and Rajsich felt strongly that Lester was someone whom the Sox should take if he fell to the No. 57 pick. But, with the season nearly over, the Sox still had yet to have a full complement of scouting looks at the young left-hander.
“I was slamming my fist down as the only cross-checker in the room who had seen him,” said Finley. “So David Chadd and Ray Crone took a flight out to Seattle and took a red-eye back to Boston.”
The amateur scouting director and national cross-checker joined Rajsich for the pitcher’s last outing of the season, in Olympia. The stuff hadn’t quite come back to the dominant form that Finley had seen at the start of the year, but that day, Lester was nonetheless impressive enough to show that the dead-arm had been fleeting, and that there were no real injury issues in play.
For the first time in months, Rajsich recalled, Lester bumped 90 mph that day, and his fastball sat comfortably at 87-88 mph. His command was strong, and overall, the performance was better than what most scouts had seen from the left-hander that summer.
“He threw a one-hitter, he might have hit a homerun,” said Chadd, who is now in charge of the Tigers draft. “I think the decision was made at that point that if he got to our pick, we were going to take him.”
THE PICK ... AT A PRICE
It wasn’t quite that straightforward.
A consensus had formed that Lester was clearly on the short list of players that the Sox would consider in the event that he fell to No. 57. Still, the team remained enamored of others in the 2002 draft.
According to multiple sources, the Sox likely would have taken outfielder Jeff Francouer had he remained available when their first pick rolled around. But the toolsy outfielder instead ended up going to the Braves much earlier, with the No. 23 pick.
There was also significant interest in Oklahoma fireballer Jonathan Broxton, with Chadd – the man in charge of the Sox’ draft – feeling particularly bullish on the big right-hander. But even though Broxton remained available when Boston’s pick arrived, lasting three more picks until the Dodgers plucked him at No. 60, Chadd decided to go with the scouts who had the strongest conviction in the room.
The unwavering advocacy of Finley and Rajsich, coupled with what Chadd and Crone had seen to back up their reports, convinced the Sox to take Lester. He became the first draft pick under the new ownership group.
“That pick was a product of good scouting by David Chadd, Ray Crone, Dave Finley, and Gary Rajsich,” observed Epstein. “Organizations can sometimes make mistakes by getting off really talented players due to a few poorly-timed off performances during the scouting season. David did a great job making sure that didn’t happen with us and Lester.”
But as excited as the Sox were to select Lester, they still had to sign him. And, in fact, some teams had been deterred by the idea that the left-hander was going to seek a seven-figure bonus in line with a late-first round or sandwich pick.
That had not been a deterrent to the Sox in the selection process, however. As the owner of the Marlins, Henry had given his scouting department the backing to acquire elite talent, even at a great cost. The first draftee under Henry was Josh Beckett, who received an unprecedented four-year, $7 million, major-league contract after the Marlins made him the No. 2 overall pick in the 1999 draft.
Henry, Werner and Lucchino similarly empowered the Red Sox amateur scouting department that summer.
“We took the best player available,” said Chadd. “It was always clear to me early on from ownership that we would have the ability to do it.”
Even so, the process was surprisingly drawn out, to the point where Lester thought he might end up enrolling in school. He had an appealing scholarship offer to pitch at Arizona State, where on his recruiting trip, he had taken note of an undersized shortstop name Dustin Pedroia in an intrasquad game.
“I never actually met him. I do remember seeing him,” Lester recalled with amusement. “But I didn’t get to see the beginning of the Laser Show.”
As the summer stretched on, and August arrived, Lester said that he and his family “were scrambling a little bit” as they tried to figure out their next step. There had been, he recalled, miscommunication with the club, the seeming byproduct of the new scouting department.
One member of the Sox organization had told Lester that the team had agreed to his asking price. Another told him that was not the case. Somewhat puzzled, Lester began exploring a transfer to a junior college – something that, in the era of the draft-and-follow process – would have bought the sides more time to negotiate.
But shortly before the enrollment date for ASU, Lester and the Sox came to an agreement for a $1 million bonus in mid-August.
“That’s kind of how I got drafted by the Red Sox,” said Lester. “[Getting taken in the first round] didn’t happen for a reason. I was happy with that.”
THE OUTCOME
The returns on the rest of that year’s draft were minimal for the Sox. Of the players they signed, only two (fourth-round pitcher Chris Smith and eighth-round outfielder Brandon Moss) have reached the majors, and both have performed in marginal roles.
Moss did create value as part of the deal for Jason Bay, just as ninth-rounder Tyler Pelland – a left-hander out of Vermont – offered value as part of a deal for Scott Williamson in 2003. But, ultimately, the Sox received a limited influx of talent with 48 of their 49 picks that year.
But their first pick of the 2002 draft? That was a gold mine. Lester fulfilled every hope and then some that the Sox had for him. It took little time for the young left-hander to convince the club that its first selection of that draft would pay tremendous dividends.
That fall, Chadd went to Fort Myers to check in on the team’s young prospects in the Florida Instructional League. And what he saw from his top draft pick in a side session convinced him that the Sox had made the right pick.
“He wanted to be perfect on every pitch. He wasn’t just getting the ball and throwing for 30 minutes. He was trying to locate, trying to locate his breaking ball, trying to get a feel for his changeup,” said Chadd. “Every pitch had a purpose for Jon. At 18 years old, he just carried himself in such a professional manner. That set a spark for me that this kid was going to be something special.
“Jon Lester made that happen,” continued Chadd. “Nobody else. Jon worked to become what he is.”
And what Lester is has exceeded even what the Sox thought he could be, or what they thought they could accomplish in the 2002 draft.
As Lester prepares to make his pitch for his 20th win of 2010, the Sox have yet another reminder of their good fortune to have acquired him. Pitchers of his stature, as Finley noted, “very, very rarely” are there for the taking in the second round. And they just as seldom exceed the best-case projections that a team places on them.
In a year when the Red Sox’ championship ambitions will go unfulfilled, the Sox recognize that they nevertheless have a pitcher who can serve as a cornerstone of their title hopes for years to come.
“We got lucky,” said Finley. “We got lucky that he got to us. And it’s very lucky when a draft pick overperforms.
“My report had him as a No. 2 starter on a championship team. He’s better than that. … To me, he’s a No. 1 starter on a championship team.”