1998 Yankees Diary, Draft Day: One that could have been among New York’s best

Twenty-five years ago today, everything was coming up roses for the Yankees organization. They had a budding juggernaut in the major leagues that would win its 39th game against 13 losses that night. They had legitimate prospects like outfielder Ricky Ledee, third baseman Mike Lowell, and first baseman Nick Johnson pushing toward the big leagues (and their top pick from 1996, Eric Milton, had helped them net Chuck Knoblauch). Their second selection in the 1997 draft, reliever Ryan Bradley, was tearing it up in his debut season and on the verge of a promotion to Triple-A. They had a World Series title under their belt from 1996, and the league hadn’t yet set up the rules to stop them from acting like the George Steinbrenner Yankees.

This all meant that on June 2nd, the first night of the 1998 MLB Draft, the Yankees could select any eligible player they’d like. As long as they were willing to pay the bonus demand, they could sign him. There were no bonus pools or slot limits, just 50 rounds of opportunity to improve the franchise. Unlike previous years when they had lost their first-round pick after signing a major league free agent, the Yankees were choosing 24th overall. They also had the rare opportunity to choose in the supplemental first round at No. 43—a compensatory pick because they had failed to sign Tyrell Godwin, a North Carolina high schooler and their ‘97 first-rounder. There was a chance for the ‘98 draft to be historic, just like the big league team, but it would end up as one of the great “what-ifs” of the era.

Perhaps the failure to sign the athletic Godwin affected the strategy of the Yankees’ organization when their first pick was on the clock. They had serious interest in a switch-hitting infielder from Mount Saint Joseph High School in Baltimore, who had idolized Don Mattingly and was a clear first-round talent but also had seven-figure bonus demands and the option to play at Georgia Tech. (Although the Red Sox picked him, he indeed became a Yellow Jacket.) The Yankees felt better about meeting Mark Teixeira’s price in 2008 when they signed him to an eight-year, $180 million contract to play first base for them.

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Drafting and signing Teixeira in the first round would have made the 1998 draft one of the Yankees’ best ever, but they passed on him and chose 6-foot-6, 190-pound, lefty-hitting Andy Brown out of Richmond, Indiana. Brown was athletic, he fit the physical profile of someone who would thrive in Yankee Stadium were he to reach his potential, the organization liked his makeup, and, importantly, he was signable. He agreed to a bonus of just over a million dollars, and that allowed the Yankees to get aggressive with their next pick.

Like Teixeira, there was another phenom who interested the Yankees at No. 24. This one was a right-handed pitcher from University City High School in San Diego, and he too had placed a high bar on his desired bonus. Signability was very much in question for Mark Prior, to the point where he appeared willing to sign with only one of four teams. One of them was the Yankees. Failing to sign their first pick didn’t seem like something the Yankees wanted to risk, but they were willing to roll the dice with Prior at 43rd overall. Had they taken him first, no one would have flinched. He was highly-regarded for his size (a sturdy 6-foot-5), his stuff, and, perhaps most of all, his ultra-clean mechanics. Prior was considered low-risk for injury, and he had the makings of a No. 1 starter.

The Yankees were willing to meet Prior’s reported asking price, and they may even have exceeded it, but after negotiating through the summer, the two sides were unable to come to an agreement. Depending on the source, the Yankees’ offer to Prior may have reached $1.5 million, but that was not enough to keep him away from Vanderbilt. He later transferred to the University of Southern California, became the presumptive top prospect in college baseball, and was talked about as a potentially generational talent.

Prior is still mentioned as one of the best amateur pitching prospects of the last few decades, and it was the Cubs who were in position to draft him at No. 2 overall in 2001 after the Twins chose local kid Joe Mauer.

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Prior lived up to the hype at the beginning of his MLB career. He was in the bigs by 2002, made the All-Star team and finished third in the Cy Young voting in ‘03, and put up 16.6 WAR over his first four seasons. And then it was over. The pitcher with the near-perfect mechanics, who was not supposed to get hurt, got hurt. He never threw another major league pitch after age 25 (though he at least won a World Series in 2020 ... as the Dodgers’ pitching coach). Some blamed his heavy workload for his breakdown, but who knows? Pitchers get hurt, and unfortunately Prior was one of them. Would the Yankees have been able to develop him differently to produce a different outcome? We don’t know that either, but there is no reason to think that would be true.

In the second round, New York chose a lefty from Louisiana State University named Randy Keisler. Those hoping for a second coming of Louisiana Lightning would have been heartened by Keisler’s strong minor league performance, and he moved quickly through the minors to make his MLB debut in 2000. After a promising five-inning stint against the hated Red Sox, things quickly went south for Keisler as a Yankee. He was rocked by big league hitters, was unable to hold down a rotation spot in 2001, and was out of the organization after getting injured and missing the 2002 season.

Before we hit the most famous ‘98 Yankees draft pick who actually became a Baby Bomber, let’s go rapid fire through a few other notable names:

• Round 6: P Brett Jodie — Briefly a Yankees in 2001, the University of South Carolina righty was traded to the Padres bring back Sterling Hitchcock for the pennant run. Jodie eventually became manager of the then-independent Somerset Patriots, succeeding ‘70s Yankees icon Sparky Lyle from 2013-19.
• Round 14: P Brett Weber — A right-hander from Illinois, Weber threw his last professional pitch for the Yankees in 2000, but after retiring, he eventually joined the organization and is now the team’s instant replay guru.
• Round 20: OF Dusty Rhodes — A teammate of Weber’s at Illinois, but unfortunately not as heroic as the primary baseball Dusty Rhodes or as famous as the The American Dream.
• Round 34: P Brandon Claussen — JUCO lefty from Texas who did make the Yankees eventually ... for a grand total of one start. He was then traded at the deadline to the Reds for Aaron Boone. My oh my, what an impact to have on not only 2003, but 2018 and beyond.
• Round 47: 3B Jeff Nettles — Yes, this is Graig’s son. He got to Triple-A Columbus but never to The Show. He then played for his dad’s old friend, Lyle, with the Patriots for the better part of 2003-12.

Now, to look back on perhaps the biggest swing the Yankees took in the 1998 draft, and one of the bigger swings they’ve taken in their draft history: the selection of Drew Henson with their third-round pick.

Henson was the type of athlete organizations dream about. He was one of the top quarterback recruits in the country, out of Brighton High School in Michigan. He committed to his home-state Wolverines over Florida State, and he had every intention of playing football in college. But he was also Baseball America’s High School Player of the Year and a rock-solid top prospect as both an infielder and a pitcher. He looked like he was created in a lab at 6-foot-5 and 220 pounds, and the buzz around him was special. Here’s what his high school coach had to say about him prior to the baseball draft:

“Do you know how there are all the stories these days about what’s going to happen when Michael Jordan retires?” Mark Carrow, Henson’s baseball coach at Brighton High, told Sports Illustrated in 1998. “About how there’s going to be a void, an absence of superstars? I think Drew Henson is the one who can fill it, who can stand on that kind of pedestal. I honestly believe that.”

No pressure, Drew. With Henson’s commitment to football, teams shied away from him in the baseball draft. But the George Steinbrenner Yankees had money, were willing to spend it for special players, and always had a thing for guys with football backgrounds. They selected Henson at No. 97, gave him an unheard-of (at the time) $2 million bonus that stipulated he would leave the Yankees at the end of July every summer he was at Michigan so he could play football, splitting time with some former Montreal Expos draft pick named Tom Brady. At age 19 in 1999, Henson had 13 homers and 12 doubles while batting .280/.345/.480 in 284 plate appearances for rookie-league Tampa. He immediately jumped into Baseball America’s top 100 prospects in the game, and it looked like the Yankees had pulled off something big.

By the next year, Henson was no longer a Yankee. Perhaps concerned about Henson’s ability to make enough contact to climb the ladder to the big leagues or his potential to choose football over baseball in the long run, the Yankees traded him to the Reds in July 2000 as part of the package for big league lefty Denny Neagle. (The veteran had at least a mild impact on the World Series champions, as he threw 4.2 solid innings in the Game 4 win against the Mets.)

Unable to give up on the Henson dream, the Yankees stunningly re-acquired him from the Reds and Steinbrenner gave him a six-year, $17 million contract to commit to baseball only. Henson entered the 2002 season as the No. 9 prospect in all of baseball, one spot ahead of Teixeira and seven spots behind Prior. Imagine the Yankees maybe having their top three picks from the 1998 draft all in the top 10 prospects of the league after they had just been to four straight World Series?

Alas, the promise of Drew Henson never came to fruition. After trading away Lowell because of their commitment to Brosius, the hope was that Henson could replace Brosius at third base after he retired. His career at third for the Yankees lasted nine at-bats. In 2016, Brian Cashman dubbed dumping Lowell as the worst trade of his career.

You hear scouts say, “He’s what they look like” when they refer to prototype big leaguers, and that would have been an understatement for Henson. Not many looked like him. The same awe inspired by viewing Aaron Judge* in person was present when Drew Henson walked past. Andy Brown never made it past Double-A, Mark Prior never threw a major league pitch for the Yankees, and Drew Henson didn’t reach the superstardom foretold for him. It was a great year for the Yankees at the major league level, but their 1998 draft will be remembered for what could have been.

*Last fun fact: Henson spent some time in the Yankees’ organization after he retired. That run included a stint as an instructional league hitting coach for Judge and Gary Sánchez. The ties that bind!