There are eight million stories in the naked draft. Here are a few of them. Reader beware—this edition is rife with benefit-of-hindsight second-guessing.

I Didn’t Realize the Value of a First-Round Pick

In 1982, Montreal signed Type B free agent Tim Blackwell, a 29-year-old reserve catcher with career rates of .230/.332/.306 to that point. Though they were in need of a backup catcher, their starter was the durable Gary Carter, so they could have survived with Brad Gulden, who was also in the organization. Signing Blackwell cost them the 17th overall pick, which the Cubs used on Whittier College infielder Tony Woods. Despite having attended Richard Nixon’s alma mater, Woods wasn’t tricky enough, and topped out at Triple-A. Players still on the board at that point included Todd Worrell (drafted with the 21st pick in the first round), David Wells (the second pick of the second round), and high schoolers Barry Bonds and Barry Larkin, who both went later in the round, but did not sign.

Often compensation picks don’t amount to anything, but we who grew up as Yankees fans spent quite a few years being bitter about the outcome of the 1983 draft. The Yankees didn’t pick in the first three rounds, having signed free agents Steve Kemp from the White Sox, Bob Shirley from the Reds, and Don Baylor from the Angels. All three teams got major leaguers out of the picks they received for losing these players to the Yankees on the open market. The White Sox, picking 13th overall, took high school righty Joel Davis (Roger Clemens was still on the board for another five picks). Davis wasn’t anything special, but he did make it to the majors, which is more than you could say for most Yankees draftees at this time. The Reds picked up New York’s second-round pick, and spent it on catcher Joe Oliver. Though not a great player, Oliver did play over a thousand games in the majors, and was the regular backstop for the 1990 World Champion Reds. The Angels had to settle for Wally Joyner with the Yankees’ third-round pick.

Missed Him by That Much

Of the 22 Hall of Famers from the draft era—that is, Hall of Famers who were subject to the draft—just one of them wasn’t drafted at all. That was 2006 inductee Bruce Sutter, who wasn’t selected in 1971, and was signed by the Cubs as an undrafted free agent. Of the remaining 21 with plaques in Cooperstown, 15 were taken in the first three rounds. From among the outsiders left over, Wade Boggs was taken in the seventh round in 1976; Goose Gossage went in the ninth round in 1970 (the White Sox hit the relief pitching mother lode that year, having nabbed Terry Forster in the second round); Nolan Ryan was the Mets‘ 12th pick in in the inaugural draft of 1965; and the Phillies, in their wisdom, took Ryne Sandberg in the 20th round in 1978. Care to guess who the other two were?

Missed Him by That Much II

Four Hall of Famers were drafted in the second round: Johnny Bench, George Brett, Mike Schmidt, and Cal Ripken, Jr. Bench, a high school catcher, was taken by the Reds in 1965 just one round after they had spent their first choice on Bernie Carbo. Seven catchers had come off of the board before Bench was selected, including three in the first round (the best of these was Ray Fosse, the seventh player taken overall). Bench was the 16th pick of the second round.

Brett and Schmidt were drafted back to back in 1971’s second round, with Brett going with the fifth pick of the round, then Schmidt with the sixth. The first overall pick that year belonged to the White Sox, and they used it on high school catcher Danny Goodwin. In a case that soured scouting directors on first-round catchers for a generation, Goodwin didn’t sign and went off to college. Four years later, the Angels made him the first overall pick in the 1975 draft. This time he signed, and the Angels gave him a cup of coffee that September. Unfortunately, despite some very solid minor league numbers (though these were undoubtedly goosed a bit by the Texas and Pacific Coast Leagues), he was unable to become a major league regular, batting just .236/.301/.373 in 252 games.

There were some solid major leaguers chosen in the first round of that 1971 draft, though. Lefty fireballer Frank Tanana was taken with the 13th overall pick, and Jim Rice‘s name was called by the Red Sox two picks later. The Dodgers picked up the versatile Rick Rhoden with the 20th pick, and the Pirates got eventual Houston favorite Craig Reynolds with the 22nd. As for the Royals and Phillies, eventual selectors of Brett and Schmidt in the second round, they bet on pitching in the first. The Royals picked Roy Branch, whose major league career was limited to a cup of coffee with Seattle in 1979. The Phillies were a bit more perceptive with their first-round pick, taking righty pitcher Roy Thomas, who would eventually have a few successful campaigns as a reliever with the Cardinals and Mariners—though not before the Phillies, who were the trading wild men of their day, swapped him to the White Sox with infielder Alan Bannister and pitcher Dick Ruthven in return for the 37-year-old Jim Kaat and a journeyman minor league infielder.

Both Brett and Schmidt were shortstops at the time of their drafting, the former in high school and the latter in college. They were, of course, not the first shortstops chosen, though they were the only shortstops selected in the second round. Eight shortstops were selected in the first round in 1971. The most successful of these was Reynolds, followed by the 11th overall pick, Tom Veryzer of the Tigers. Veryzer thereby became the answer to a trivia question: Who was the Tigers’ shortstop before Alan Trammell? Despite having what could charitably be described as an extremely limited bat—Veryzer hit .241/.283/.294 lifetime, or if you prefer, a .211 Equivalent Average—Tigers manager Ralph Houk listed Veryzer as his second-slot hitter 40 times in 1976; Veryzer posted a .301 on-base percentage in the role, which, depending on how you look at it, might even be considered a victory for the manager.

Cal Ripken, Jr. was the 22nd pick of the second round in 1978, in what was a strong, strong draft class. Fourteen of 26 first-round picks made the majors, including the first five players drafted: Bob Horner, Lloyd Moseby, Hubie Brooks, Mike Morgan, and Andy Hawkins. Also taken in the first round were future MVP Kirk Gibson, Twins All-Star Tom Brunansky (who would hit 271 home runs in a 14-season career), and Nick Esasky, who had his best season when his career was ended by vertigo at the age of 30. The next round also featured a number of durable major leaguers, including Dave Valle, Danny Heep, Mel Hall, Darryl Motley, and Steve Balboni. No one of them, of course, was as durable as Ripken; he went two picks ahead of Motley and three in front of Balboni.

A Man Doesn’t Know What He Has Until He Loses It

The 1978 draft suggests the point that it’s not just who you get but what you do with them after making your picks. Once the free-agent era hit, the Yankees largely did without first-round picks, sacrificing them annually as compensation for their annual winter pursuit. In 1978, however, they not only retained their pick, the 26th and last of the first round, but they added two others—the White Sox signed away DH Ron Blomberg, thereby yielding the 18th overall pick, while the Red Sox signed away Mike Torrez, which entitled the Yankees to the 24th pick. Chicago’s former pick was spent on Rex Hudler, who would eventually go on to a 774-game career in utility work, though he’d suit up for the Yankees in just 29 of those games, having dealt him and pitcher Rich Bordi to the Orioles for Gary Roenicke and Leo Hernandez in 1985. Note the date: whatever his virtues, or lack thereof, Hudler spent eight seasons on the Yankees farm. Until the mid-’90s, the Yankees, adopting the stance of their owner, had absolutely no interest in employing young players.

The Yankees spent their own pick on high school righty Brian Ryder, who stalled out at Triple-A and was shipped out along with 1979 draftee Fred Toliver to the Reds in exchange for Ken Griffey. The Reds received zero return for Senior, a career .307/.375/.437 hitter to that point, but keep in mind that the deal was made on November 4, 1981, about three seconds before Griffey would have declared himself a free agent and left of his own accord.

That leaves the player the Yankees selected with the pick they had received from the Red Sox. Matt Winters was a high school outfielder from Williamsville, New York. No defensive whiz even at 18, Winters did possess unusual power and patience for one so young. In 60 games at Low-A Oneonta in 1978, he batted .261/.373/.433, the slugging percentage being driven by 11 triples. The next year, as the cliché goes, those triples turned into home runs. Today, we would notice a 19-year-old batting .282/.442/.495 in Low-A ball, and we would definitely notice if he hit .320/.416/.537 in the Sally League the year after that.

The Yankees being the Yankees, however, they sent Winters back for more Sally League seasoning—anything to stall these guys long enough that they wouldn’t force some 35-year-old off of the roster. Winters hit .325/.503/.583—that .503 OBP is not a typo, as he walked 118 times in 104 games—and he was finally promoted to Double-A, where he hit .303/.454/.515 in 29 games. The calendar turned to 1983, so it was now going on five years since Winters had been drafted. Somehow he made it to Triple-A without spending more time at Double-A. He batted .292/.439/.564 with 29 home runs and 113 walks in 133 games. That was the year that right fielder Steve Kemp was badly hurt in an outfield collision. Winters didn’t get called up. Nor did he get called up when rosters expanded. He didn’t even get a copy of the home game.

Years later, Winters told Jack Etkins (as published in Bill James’ 1991 edition of The Baseball Book) that, “I just basically knew that after that ’83 season I wasn’t going to get a shot with them… And I think that kind of took a little bit of the competitiveness out of you… All of a sudden it’s, ‘Well, what do I have to do? Do I have to hit one more home run and one more RBI?'” In fact, there was nothing he could have done to impress the Yankees. He was back at Columbus the next year, and though he was stagnating (.248/.386/.383— he lost 19 home runs, but still drew 90 walks), the Yankees held on to him for another two seasons, loaning him out to Buffalo for a while, and demoting him to Double-A.

Finally out of the Yankees organization, in 1988, Winters signed with Double-A Memphis at the behest of the Royals’ player development director, John Boles. He hit well, and made it back to Triple-A the next year. It was that May that the Royals gave him his one major league audition. He was 29. He managed two home runs in 42 games, and it was all over. That winter he signed with the Nippon Ham Fighters. Over the next five seasons, he hit 160 home runs and was selected to two all-star teams. We’ll never know what Winters might have done in the majors had he been promoted on a reasonable schedule instead of actively suppressed. Perhaps with his “old player skills” he wouldn’t have lasted long, but it’s clear that he had something to offer. The Yankees didn’t care.

Going back to 1977, the year before the Yankees drafted Winters, the team drafted 15th in the secondary phase of the now-defunct January draft. With that pick, they selected another outfielder, a Diablo Valley College player named Willie McGee. They sent the teenager to Oneonta, and he moved up the ladder just ahead of Winters. He didn’t get a lot of great interest until he repeated Double-A in 1981. The then-22-year-old McGee batted .322/.360/.454, and he stole 24 bases in 31 tries. That fall, at precisely the moment the Yankees were looking to add speed to their roster, they made a much-lamented deal with the Cardinals, sending McGee west in exchange for pitcher Bob Sykes, who never did pitch in New York. Again, picking the right player is only half the battle. After drafting comes development, and one without the other doesn’t lead to anything except disappointment.

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"Seven catchers had come off of the board before Bench was selected, including three in the first round (the best of these was Ray Fosse, the seventh player taken overall)."

My mother taught Ray Fosse in high school, in his home town of Marion, IL. I always thought it was poetic justice that Pete Rose, the man who trashed Fosse's shoulder in an exhibition game, ended up incarcerated in Marion.
Peter Rose - Charley 455hole.
I'm pretty sure that one of Ray Fosse's brothers ended up as one of the prison guards with responsibility over Rose.
"Care to guess who the other two were?"
I'm pretty sure Ozzie Smith was one of them, and I'm guessing Rollie Fingers was the other.

no answer to your trivia question about who the other two Hall of Famers are that were taken outside the first three rounds?
I can look it up (no pun intended), but its far more fun to venture a guess.

Eckersley and Henderson?
I'm going to split the difference of the last two guesses and say Ozzie and Henderson are the two other HoF taken...

Fingers is an interesting guess (since the reliever HoFs have a late-round vibe) but I think he and Catfish Hunter were signed before the draft came into play (early 1960s)...Eckersley was a big deal SP...

My other guess would be Eddie Murray --- the Orioles had so many prospects around then (early 1970s -- Flanagan, D.Martinez, Dauer, K.Garcia (don't laugh), Mike Dimmell, Jim Fuller, Paul Mitchell, Don Hood, and all those expansion draftees: Jesse Jefferson, Bob Gallasso, Mike Parrott, Mike Darr) I could see him going in the 8th round...
NPB, you got it - both Ozzie and Rickey were fourth rounders.
It'd be real interesting to dig up old scouting reports and scouting commentary on Rickey Henderson...
The treatment of Winters just gives me another reason to hate the Yankees. The story sounds like a bad ending to Ryan Howard's wait behind Jim Thome. Didn't any other team offer something for him?