The 10 most interesting Rule 5 draft picks, 1981-2007

In this series we’ve discussed some intriguing Rule 5 picks from 1903 to 1940, from 1941 to 1966, and from 1967 to 1980. Now we’ll bring it home.

But first, let’s quickly review just what the Rule 5 draft is.

How it works

In its early years, the Rule 5 draft was held at the immediate conclusion of the regular season, at the end of September or the beginning of October. In the modern era, it takes place during the MLB winter meetings.

To be eligible for the draft in its current form, a player:

{exp:list_maker}Is not included on the 40-man roster of the organization holding his contract
Has been in the minors and/or majors for at least four years, if he was signed after his 19th birthday
Has been in the minors and/or majors for at least five years, if he was signed before his 19th birthday {/exp:list_maker}Rule 5 has always included a provision designed to encourage teams to draft carefully: For the entire first season after he’s drafted, the Rule 5 pick must remain on the drafting team’s 25-man active major league roster. If his team wishes to farm him out during that season, first it must put him on waivers, and if he’s unclaimed there, then offer him back to the club from which he was drafted, and that team has the right to take him back for the waiver price. Very often, however, the player’s original organization doesn’t have room for him, and declines the offer, and the drafting team then becomes free to handle the player as it would any other.

During that first season, Rule 5 draftees can be traded or sold to a new team, but the new team takes on the restrictions of being unable to send him to the minors without first going through waivers, then offering him back to the team that lost him in the draft.

Minor league teams also can participate in the Rule 5 draft (indeed in the early years of the arrangement, with minor league teams operating independently from parent major league organizations, this portion of the Rule 5 draft was a very big deal). As the draft currently is structured, Triple-A teams can draft any player eligible from Double-A, and Double-A teams can draft any players who are eligible from Single-A, in both cases for a nominal fee. Players chosen in the minor league part of the draft don’t need to be offered back to their original teams for any reason.

The drafted

Clearly, the manner in which the Rule 5 draft is set up means that first-tier players typically aren’t involved; teams rarely allow their stars and top prospects to be left unprotected off the 40-man roster. The great majority of players drafted under Rule 5, today and in the past, have been long-shot prospects (and in past decades many were major league-level role players as well, but the advent of free agency rendered that practice obsolete).

But not all Rule 5 draftees are destined for oblivion. Occasionally over the years—maybe more often than occasionally—a genuine star, even a superstar, has emerged from the Rule 5 process. In this series we’re identifying those cases, and examining as well those situations in which a Rule 5 draftee didn’t turn out to be much of a player, but his story is intriguing nonetheless.

10. Fernando Viña

Dec. 7, 1992: Drafted by the Seattle Mariners from the New York Mets.

He was a great talent by no means, but Viña, sort of your stereotypical undersized “scrappy” second baseman, made the very best of limited abilities, and forged a career that consisted of surpassing expectations and defying long odds, over and over again.

Start with the Mets, not considering Viña a serious prospect, and allowing him to be exposed to the Rule 5 draft. The Mariners grabbed him but were unimpressed, and would return Viña to the Mets’ organization in June of 1993. In New York he would make it to the majors in 1994, but only in a backup role, and following that season the Mets tossed him off to the Brewers as a player-to-be-named-later.

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Viña was a utility man in Milwaukee as well, a sure-handed guy who swung a decent contact-hitting left-handed bat, but lacked power, and his speed and range were average at best. But he was a battler, and in Ron Hunt-throwback fashion one of the elements he incorporated into his game was the willingness to get in the way of a lot of pitched balls. By his second season with the Brewers Viña had worked his way into the first-string second base job.

Frequent and non-trivial injuries were a also regular element of Viña’s game, but when he managed to keep himself healthy he played darn good baseball. In 1998, among National League second basemen only Jeff Kent and Craig Biggio surpassed Viña’s OPS+ of 114, and he made the All-Star team.

But he would spend most of the ’99 season on the DL, and the Cardinals would then pick him up for modest trade payment. In St. Louis again Viña would battle through injuries to claim and keep the starting job, and in 2001 and 2002 he won back-to-back Gold Glove awards.

9. Bip Roberts

Dec. 10, 1985: Drafted by the San Diego Padres from the Pittsburgh Pirates.

Roberts presented a story similar to Viña’s in several ways: both were slightly-built second basemen (at 5-foot-7, 165, Roberts was even smaller than Viña) who cruised under the star-prospect radar as Rule 5 draftees; both emerged from obscurity as stars; and for both the stardom was fleeting, due to chronic injuries.

The differences between them were that Roberts had terrific speed and was an outstanding high-average hitter, and that defensively Roberts was, well, the sort of second baseman who ends up playing a lot in the outfield.

8. Jose Bautista

Dec. 7, 1987: Drafted by the Baltimore Orioles from the New York Mets.

A pretty big guy, but not a hard thrower at all, Bautista was a pitcher who depended upon outstanding control to achieve success. Not that he achieved much: Upon being drafted by the Orioles, Bautista made the leap all the way to the majors without benefit of any Triple-A experience and delivered a decent performance in their starting rotation in 1988, before regressing. He then bounced around and had a moderate journeyman’s career.

No, this situation became truly interesting when …

7. Jose Bautista

Dec. 15, 2003: Drafted by the Baltimore Orioles from the Pittsburgh Pirates.

… the Orioles decided that they’d had so much fun with the previous Jose Bautista that they’d better grab this one too. And from that point things became downright kooky.

There wasn’t anything remarkable about this fellow’s minor league performance. A third baseman who’d spent three years in the Pirates’ system without rising above high-A, Bautista had hit all right, but nothing great, either in terms of power or average or strike zone discipline, nor did he have speed or a great glove. Nevertheless Baltimore’s two-headed GM (Jim Beattie and Mike Flanagan) decided to give him an opportunity.

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Bautista made the Orioles’ roster, but by no means the starting lineup: Melvin Mora stepped forward and grabbed the third base job and had a great year, and Bautista was relegated to a strict scrubeenie role. By early June he’d appeared in just 16 games, and had only 12 plate appearances, and the Orioles were no longer willing to devote a roster slot to him. But before offering him back to Pittsburgh, they placed Bautista on waivers, and the last-place Tampa Bay Devil Rays claimed him.

The struggling Devil Rays would seem to be an organization that would benefit from investing some patience in this prospect, but no: After giving Bautista just 15 PAs in three-and-a-half weeks, Tampa Bay gave up on him, accepting a purchase offer from the Royals. Yet neither would Kansas City, also a cellar-dweller, demonstrate any commitment, as just a month and only 26 plate appearances later, the Royals traded Bautista to the Mets.

Bautista’s stay in New York would be the briefest yet: Their only interest was in packaging him as part of a trade with Pittsburgh, completed on the very same day. Thus his original organization had gotten Bautista back, after a bizarre odyssey in which he’d been the property of four other franchises within the space of two months. And the Pirates, as Bautista’s original organization, were the one team that held the capacity to farm him out at this point—and yet they declined to do so, keeping him in the majors for the rest of the 2004 season while using him in just 23 games and 43 PAs.

All in all it was a weird fuss for so many ball clubs to be making over a guy with entirely ordinary ability. Once he’s finally gotten the chance to play regularly in the majors in 2006-2008, Bautista has proven to be a blandly unexciting journeyman.

6. Jay Gibbons

Dec. 11, 2000: Drafted by the Baltimore Orioles from the Toronto Blue Jays.

This guy, on the other hand, proved to be a solid major league talent; not a star, but a meaningful asset. And the puzzling issue regarding him is exactly why Toronto GM Gord Ash allowed Gibbons to be exposed to the Rule 5 draft in the first place.

True, he wasn’t the most athletic of prospects, and true as well, he was a year or two older at each of his minor league levels than the guys who project as stars. But he’d simply destroyed the pitching to which he’d been exposed: In four minor leagues in three seasons, Gibbons had hit .397 (Rookie), .305 (low A), .311 (high A), and .321 (Double-A), all with excellent power. You’d think that might be the kind of performance that would earn a spot on the 40-man roster.

5. Kelly Gruber

Dec. 5, 1983: Drafted by the Toronto Blue Jays from the Cleveland Indians.

Last time we saw two Rule 5 selections by Blue Jays GM Pat Gillick who paid off big time: Willie Upshaw and George Bell. Here was another.

Also like Upshaw and Bell, Gruber wasn’t an immediate success upon his arrival in Toronto, and benefitted from Gillick’s patience as he gradually developed. The Blue Jays were able to farm Gruber out in mid-1984 (the Indians declined to take him back), and he spent most of that season and the following one in the minors. His first full big league year wouldn’t come until 1986, when deployed by Toronto in an infield-outfield utility role, and even then Gruber didn’t hit a lick.

But from that modest beginning, Gruber’s improvement was steady and remarkable. In 1987 he wasn’t yet a good hitter, but was distinctly improved, and he became the Blue Jays’ semi-regular third baseman. By ’88 he blossomed, and would spend three years as one of the better all-around third basemen in the game; in 1990 Gruber won a Gold Glove and a Silver Slugger, and was fourth in the league’s MVP voting.

Gruber’s peak was all too brief. His ascent was quickly followed by a rapid regression, as an upper spine/neck injury took a serious toll, and his career would end prematurely. Thus his six seasons as the primary Toronto third baseman present as vivid an OPS+ parabola as you’ll ever see: 77, 113, 123, 127, 102, 72.

4. Mitch Williams

Dec. 3, 1984: Drafted by the Texas Rangers from the San Diego Padres.

Was there anything about “Wild Thing’s” career that wasn’t utterly, completely strange? Anything at all?

I’m not just talking about the fundamental issue of his managing to sustain a major league career of eight full seasons and parts of three more, appearing in more than 600 games, without ever coming close to developing the faintest hint of control. His walk rate of 544 in 691 innings was bad enough, but on top of that Williams (literally) threw in 52 hit batsmen and 44 wild pitches. (Oh, and just to make things even more interesting: 24 balks.) Wild Thing made Ryne Duren look like Bob Tewksbury.

No, that’s just the beginning of the weirdness with this guy. Consider his fielding: Williams handled 106 defensive chances in his major league career, and committed 17 errors. Yes, you read that correctly. His lifetime fielding percentage was .840, against a league average of .956. (One could logically assume the great majority of the boo-boos were throwing errors, were it not for that fact that Wild Thing’s delivery had him awkwardly falling off the mound in a chaotic flail of arms and legs, so he was in no position to field a ball cleanly either.)

And then there’s the fact that the play for which he’s best-known is surrendering the World Series-ending walkoff home run to Joe Carter in 1993—when a home run was (not surprisingly) just about the least likely outcome of a plate appearance against Williams. Over the course of his career he allowed just 49 homers; that’s right, he hit batters more frequently than he yielded home runs (a feat that, to be fair, Duren also pulled off).

Yet if all that isn’t weird enough, how about this: The Padres allow the 20-year-old Williams to be Rule 5 drafted by the Rangers. But at the end of spring training, the Rangers decide they don’t want to keep him, and offer him back to San Diego. Padres GM Jack McKeon accepts Williams, but then immediately trades him back to Texas in exchange for a 23-year-old third base prospect named Randy Asadoor. (This arrangement allows the Rangers to farm out Williams.) Asadoor, for his part, proceeds to post one of the strangest major league careers of all time: Called up by the Padres in September of 1986, he shreds big league pitching with a .364 batting average and an OPS+ of 137 in 60 plate appearances—and then never plays another inning in the majors.

3. Bobby Bonilla

Dec. 10, 1985: Drafted by the Chicago White Sox from the Pittsburgh Pirates.

Versatile, durable, and a consistently outstanding hitter for a long time, Bonilla wasn’t quite a Hall of Fame talent but he was inner circle in the Hall of Very Good. Yet Pirates GM Syd Thrift let the 22-year-old Bonilla slip through his fingers in the Rule 5 draft—whoops!—and then Thrift felt so ashamed of himself that in mid-summer 1986 he went and traded a highly talented young pitcher (Jose DeLeon) to get Bonilla back.

2. Josh Hamilton

Dec. 7, 2006: Drafted by the Chicago Cubs from the Tampa Bay Devil Rays.

His story can be filed under “Truth Stranger than Fiction” from several different angles. And among them is the complicated sequence of transactions that brought Hamilton to Texas.

It’s difficult to fault the Devil Rays for declining to include Hamilton on their 40-man roster in the 2006-07 offseason; after all, following his several lost years, Hamilton had played in just 15 minor league games in 2006.

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Under those circumstances, what’s interesting isn’t only that the Reds were willing to make the commitment, but that they were so eager to get Hamilton that they worked out a deal with the Cubs (drafting many slots ahead of Cincinnati because of Chicago’s last-place finish in 2006) to purchase him upon the Cubs’ exercise of their Rule 5 draft selection. The deal was struck for a figure of $100,000: 50 grand to reimburse the Cubs for their Rule 5 fee, and an additional 50 as profit.

Such a sum is pretty nominal within the modern major league context, and thus the wisdom of Cubs GM Jim Hendry in participating in this parlay can be questioned. This ball club was, after all, coming off a disastrous season and facing some major re-tooling of the roster; maybe giving Hamilton a shot in the Chicago outfield would be worth $50,000. But instead it was Reds GM Wayne Krivsky making twice that investment, and of course Hamilton blossomed wonderfully.

Yet that wasn’t enough to convince Krivsky to stick with Hamilton; he was quickly traded to the Rangers for the entirely unproven pitching prospect Edinson Volquez. For his part, Volquez would also blossom in Cincinnati, but it remains questionable whether Volquez will deliver more long-term value than Hamilton.

1. Johan Santana

Dec. 13, 1999: Drafted by the Florida Marlins from the Houston Astros.

He hasn’t had the best career of any Rule 5 draftee—that status still belongs to Roberto Clemente—but Santana has been tremendous, and it isn’t beyond the realm of possibility that he’ll outdo Clemente before all is said and done.

Nevertheless the Astros’ decision to expose Santana to the Rule 5 draft is defensible. In his three minor league seasons he’d racked up nice strikeout rates, but nothing overwhelming, and he hadn’t yet been effective overall: His ERAs had been 7.43, 4.69 and 4.67. He was a very young, very raw prospect; it was far from obvious that he’d make it in the major leagues at all, let alone develop into a superstar.

The curious aspect to Santana’s draft was the arrangement worked out between Marlins GM Dave Dombrowski and Twins GM Terry Ryan. Minnesota held the first draft position, and Florida the second.

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The story is that the Marlins’ preference was for Jared Camp, a pitcher in the Cleveland organization, and the Twins wanted Santana. Setting aside the question of whether preferring Camp made sense (he was 24 and in five minor league seasons had worked just 11 innings as high as Triple-A), here’s where it gets weird: The teams agreed that the Twins would draft Camp, and then the Marlins would take Santana, and they’d immediately swap them, with the Marlins tossing in $50,000 as a sweetener, covering Minnesota’s draft fee.

Does this make any sense to you? The Marlins wanted Camp. The Twins wanted Santana. The Twins had the first pick. Why in the world shouldn’t the Marlins have just let Minnesota take Santana, then taken Camp themselves? Florida would get the guy it wanted anyway, and not have to spend any extra cash.

The only downside for the Marlins would be if the Twins crossed them up and drafted Camp. But of course if that were to happen, then Florida could still attempt to negotiate a trade to acquire him. And moreover, the far larger issue is that Camp just wasn’t the sort of prospect worth investing all that much resource and effort over. As it turned out, after all this the Marlins wouldn’t even keep Camp, instead returning him to the Indians organization before Opening Day of 2000.

Score one for Terry Ryan, big time.

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