At White Sox camp in March, I reminded Konerko of that unfair matchup -- an apprehensive soft-tossing lefty vs. an all-state slugger -- described by many as the best hitter they'd seen in Arizona -- who had scouts buzzing when he was 13 years old.
I never stood a chance.
"Well, if it makes you feel any better," Konerko said, "I've hit a few since then."
A few? Modest as always, the White Sox icon is entering the final days of an 18-year Major League career that has produced 439 homers, six All-Star appearances, an American League Championship Series MVP and a World Series title.
Konerko, 38, is revered in Chicago for his 16-year stay on the South Side -- his No. 14 is expected to be retired -- but his legend took root in the early 1990s at Scottsdale Chaparral High, where it seemed clear he was destined for greatness.
"The first time you saw him swing a bat, you knew he had a chance to be a hitter," said Jerry Dawson, the longtime head coach at Chaparral who is now the pitching coach at Yavapai College in Prescott, Ariz.
Dawson, invited by the White Sox, will be one of the guests at Paul Konerko Day festivities on Saturday at U.S. Cellular Field, bringing Konerko's impressive career full circle.
"I was in the house with the family and him when he got the call that he was drafted," Dawson said. "I was in Arlington the first night he suited up in a Major League uniform and it's only fitting I be there the last time he puts it on."
As a senior catcher in 1994, Konerko hit .564 with 12 homers and 50 RBIs to help deliver the first state baseball title for Dawson and Chaparral -- which has won nine more since -- and he was the first of five players from the school to reach the bigs (Brian Bannister, Ike Davis, Charles Brewer and, most recently, Dodgers lefty Daniel Coulombe followed).
On a senior-laden team that went 31-4 and was loaded with talent, Konerko was the main attraction. I was a junior with mediocre stuff but the good fortune to be left-handed, splitting time between varsity (1-1, 5.25 ERA in two games when I wasn't shagging foul balls) and JV and under no illusion that a future on the field beckoned.
My ticket to MLB instead came in front of a keyboard, editing stories and writing headlines -- sometimes about the very guy who turned one of my pitches around 400-something feet the other way. For the less-athletically gifted among us, tracking Konerko's career -- from his selection by the Dodgers with the 13th overall pick in 1994 through the Minors and into The Show -- was, well, pretty cool.
The guy who belted a dramatic grand slam in Game 2 of the 2005 World Series is the same guy who bought Chaparral a new set of jerseys so we could keep ours as souvenirs for winning state. (His No. 9 is retired at the school; my No. 10 hangs proudly at home.)
"I don't know if surreal is the right word," Dawson said about watching Konerko's career come to a close. "It's kind of sad because he was our first one of the program and my first one as a coach. I was so proud of all of you, whether you were Major League Baseball players or not, but he's done such a good job of being an ambassador for the game."
Twenty years later, and Konerko's name is still inextricably linked with Chaparral. He is the school's career leader in homers with 21 and RBIs with 132.
"Looking back, it was a great place to learn the game," Konerko said. "[Dawson] taught me a lot of stuff that carried on into professional baseball, so I always felt like I was ahead of the game. It was a very professional atmosphere in high school."
Konerko inspired Paul Bunyan-esque tales with his slugging in those days. Just mention the grand slam he hit in a night game at Alhambra High in Phoenix during the '94 season and Dawson chuckles.
Konerko not only cleared the left-field fence -- some 385 feet away -- but he sent that ball sailing over the press box and onto the neighboring football stadium before it finally came to rest near the hash marks on the field.
"It was at night, so [the] ball was still going up when it disappeared," Dawson said.
It left everyone in awe.
"What I remember was that the ball went over the football stands that were behind left field," former teammate Chris Packard said. "I had never imagined such a thing was possible, and unless I saw it with my own eyes, I would have never thought it was possible. The guy is a legend."
Said Mike Wall, another ex-teammate: "It was probably the longest bomb I've ever seen up close. I remember it went over the light towers in left field."
None of this came as surprise to Eddie Bane, special assistant of player personnel for the Red Sox. He was a special assistant to the general manager for the Dodgers when they drafted Konerko, but he knew he was seeing something special long before that.
"I heard about Paul when he was 13 years old," Bane said. "He was a great hitter when he was 13. He's the smartest hitter in the Major Leagues right now. He knows hitting backwards and forwards."
In his typical understated fashion, Konerko is bowing out at the same time as Yankees legend Derek Jeter, whose farewell tour has dominated headlines. But Konerko's contributions -- both past and present -- won't soon be forgotten.
"I think he's a little surprised at how many people he's affected in his life," said Bane, who hoped to attend Saturday's ceremony and admitted he might get a little teary-eyed. "I think he's starting to realize it now."