One of my favorite events of the baseball year is the annual Rule 5 Draft, which takes place during the Winter Meetings in December (apparently it’s going to be earlier than that this year) and is designed to help advance the careers of players stuck in the minors. The rules are pretty simple; any player selected has to stick on his new team’s 25-man roster all season or be offered back to his old club for half the original $50,000 claiming fee. The Yankees have lost a few players to the Rule 5 gods over the years, most notably Kanekoa Teixeira (Mariners) and Zach Kroenke (Diamondbacks) last season.

Last year the Yankees traded Brian Bruney to the Nationals for the player to be named later, though they worked out a deal with Washington that gave them the first overall pick in the R5D. They drafted outfielder Jamie Hoffmann, gave him a look in Spring Training, and ultimately decided to return him to the Dodgers. A few years before that they rolled the dice with Josh Phelps. Rule 5 picks rarely stick and when they do they’re often spare parts like middle relievers or bench players. Every once in a while there will be a Dan Uggla or Johan Santana or Joakim Soria or Josh Hamilton though, which is what makes it so interesting.

For all intents and purposes, high school players drafted in 2006 and college players drafted in 2007 (or earlier, of course) are eligible for this year’s Rule 5 Draft. Through the miracle of the internet, Donnie Collins provided us with a full list of Yankee farmhands – confirmed by VP of Baseball Ops Mark Newman – eligible for this year’s Rule 5 Draft. For prospect nerds like me, it’s pretty much a gold mine. Jesus Montero, despite signing as a 16 year old in 2006, is not eligible this year. Don’t ask me how, I don’t completely understand the eligibility rules, but all I know is that the team confirmed he isn’t eligible.

There are currently 43 players on the Yanks’ 40-man roster since Al Aceves, Damaso Marte, and Nick Johnson are sitting on the 60-day DL. Johnson, Lance Berkman, Austin Kearns, Chad Moeller, Marcus Thames, Javy Vazquez, and Kerry Wood all go away once free agency starts next week. Derek Jeter, Mariano Rivera, and Andy Pettitte will come off the 40-man as well, but they’re coming back or will be replaced by someone. That puts the Yanks at 36 players, and you have to assume they’ll sign a few free agents, so let’s call it an even 40. Cut candidates include Sergio Mitre, Dustin Moseley, and Chad Gaudin, but let’s play it safe and say that two of them will be back. Reegie Corona and Royce Ring can go, ditto Steve Garrison.

That gives the Yankees four 40-man roster spots to use for protecting prospects from the Rule 5 Draft. Dellin Betances and Brandon Laird are absolute no-brainers, so we’re already down to just a pair of spots. I see four realistic candidates for these spots: George Kontos, Lance Pendleton, Ryan Pope, and Craig Heyer. Almost everyone else on the list can be left unprotected for obvious reasons, and I don’t believe Melky Mesa and Bradley Suttle are advanced enough to stick on a big league 25-man roster all season. The odds are overwhelmingly in favor of them being returned at some point should they get picked.

Let’s break down the cases for Kontos, Pendleton, Pope, and Heyer…

George Kontos
The Greek God of Pitching returned from Tommy John surgery this June and transitioned from starter to reliever. Kontos pitched well after coming back from surgery (3.37 FIP in 45 IP) and is currently getting his brains beat in (8 IP, 20 baserunners, 13 runs) like every other pitcher in the Arizona Fall League. The 25-year-old righty has firm stuff (low-90′s heat, good slider, eh change) tailored for a relief role, which is realistically the only spot he’d fill for the Yanks. His minor league strikeout rate at and above Double-A is very good (8.6 K/9), but the walks are a touch high (3.5 BB/9) and he’s always been homer prone (one longball for every eleven innings pitched as a pro). The equipment is there for Kontos to be a serviceable reliever.

Lance Pendleton
The Yanks’ fourth round pick in 2005, Pendleton missed the entire 2006 season due to Tommy John surgery (damn Rice pitchers). He’s been an absolute workhorse ever since, throwing a total of 445.1 innings (3.28 FIP) in the last three years, including 154.2 this year. The elder statesmen of this group, Pendleton is already 27, so his solid but not overwhelming rates (8.0 K/9, 3.3 BB/9, 0.9 HR9) have to be taken with grain of salt since he’s always been older than the competition. I’m not sure if and how much the scouting report has changed through the years, but he was a low-90′s fastball guy with a curve and change back when he was drafted. It’s enough that he can start, and frankly he’s probably no worse than Moseley. At the very least he’s cheaper.

Ryan Pope
Pope’s always been an interesting case just because he the second player ever drafted out of the Savannah College of Art and Design. A year ago we wouldn’t have even been having this conversation, but the 24-year-old righty put himself on the map this summer after shifting into a relief role. He went from a fringy guy without swing-and-miss stuff (6.9 K/9 before 2010) to a dominant reliever, striking out 9.7 batters per nine while walking just 1.8 unintentionally. The homers are a bit of an issue (0.9 HR/9 as a reliever), but that’s life. We have to be careful with the sample (just 59 IP as a reliever), but Pope’s definitely put himself into the mix as a bullpen prospect.

Craig Heyer
Heyer’s been sneaky good since signing as a 22nd round pick back in 2007, earning the praise of Keith Law recently. Still just 24 years old, his walk (just 14 unintentional walks the last two seasons, or 0.8 BB/9) and homer (0.3 HR/9 career) rates are the stuff of legend, but the problem is that he doesn’t miss many bats (5.1 K/9). Heyer also has yet to pitch above High-A. The Yankees sent him (and Pope) to the AzFL to get a longer look, so you know he’s at least on their minds. The stuff is fine (click the link above for a scouting report), but the experience isn’t.

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Of those four, I’m taking Kontos and Pope. Pendleton will almost definitely be selected since cheap spot starters/long men are always in demand around the league, but that’s the cost of doing business. Heyer might get picked, but chances are he’ll be offered back at some point. Kontos and Pope have by far the best chance of being impact players for the Yankees in 2011, and more importantly have a better chance of sticking on another club’s 25-man roster next year. The Yanks need to keep replenishing their pipeline of young and cheap strikeout relievers, and these two are next in line. If they somehow clear up a fifth 40-man spot, I’d go with Pendleton over Heyer given how much closer he is.

If you’re losing players in the Rule 5 Draft, it’s a good sign, not necessarily a bad thing. It means you have players in your system other teams covet, which is one of the caveats of a deep farm system. The Yanks have some tough decisions to make this year and well definitely lose a player or three, but that’s life. the important thing is that they keep the right ones.

Hoffmann, Kontos photos both courtesy of the AP.

Update (10:30am): I’m an idiot. Tosoni was drafted in 2005, but not signed until 2006 as a draft and follow. He has one more year left before he’s Rule 5 Draft eligible. So, this is embarrassing…

Talk about topics I didn’t think I’d be writing about when I woke up yesterday morning. When the Yankees traded enigmatic reliever Brian Bruney to the Nationals, they received one of those generic players to be named later, and no one thought much of it. Bruney was gone, meaning the Yanks saved some cash and I would need a new reliever to despise (early favorite: Phil Coke). Not long after the trade, I mused that maybe the return would be the rights to the first pick of Thursday’s Rule 5 Draft, and whaddya know? That’s exactly what they’re getting.

Trades involving Rule 5 picks aren’t uncommon. The Reds worked out a deal with the Cubs to get Josh Hamilton in 2007 because they were afraid the Marlins would take him before they got a chance to pick. The Cubs took Hamilton with the third pick, then immediately send him to Cincinnati for $100,000.  The same basic thing is happening with the Yanks and Nats this year, except the player the Nats take will be sent to the Yanks as the PTBNL. And yes, the Yanks will tell the Nats who to pick, otherwise this deal wouldn’t make sense.

As per the Rule 5 Draft rules, the Yanks will have to keep the player on their 25-man Major League roster all season in order to retain his rights permanently. If they don’t, then the player has to pass through waivers (if a team claims him, the Rule 5 rules follow him) before being offered back to his original team. I thought it was a very shrewd move by the Yanks, because now they get to choose their return for Bruney from a massive pool of players, rather than being limited to one organization and the players they’re willing to move.

Through the magic of common sense, we know that players from 28 teams are possible picks. A team can’t pick a player from it’s own system, so that rules out everyone in the Nats’ system, and the Yanks aren’t going to have the Nats take one of their own (New York’s) prospects. It’s possible to unearth a gem in the Rule 5 Draft (Dan Uggla, Shane Victorino, and Johan Santana are R5D alumni), thought it’s extremely unlikely. The latest CBA took all the fun out of the Rule 5, because it gave teams another year before they had to protect players.

So, realistically speaking, the Yanks don’t have many places to hide a Rule 5 player. There’s always the back of the bullpen and the bench, and given their current situation, leftfield. I’m going to rule out an infielder because the Yanks felt compelled to add the likes of Eduardo Nunez and Reegie Corona to the 40-man last month. Let’s run down some possibilities after the jump, listed alphabetically.

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Nothing gets me excited quite like the Rule 5 Draft, one of baseball’s more underappreciated sources of talent. If you’re unfamiliar with how the R5D works, Wikipedia does a pretty good job of explaining it. Basically, it’s a way to help players stuck in the minors advance their careers. If they’ve been playing pro ball for at least four years (three for college draftees) and are not on the 40-man roster, they’re eligible to be drafted. Their new team has to keep them on the 25-man Major League roster all season, otherwise the player’s old team can take him back if they want. That’s a really quick and dirty explanation, but it’ll do.

The actual draft is held on the final day of the Winter Meetings in early December. This year it’s on the 10th. Even though the draft isn’t for another few weeks, rosters do have to be set fairly soon. I don’t know the exact date, but last year it was November 20th, so it can’t be too far away.

For the most part, teams will use the R5D almost like a temp agency; a means to find cheap labor. They won’t (or shouldn’t) go in looking for a franchise cornerstone, because they aren’t going to get it. The best young players always get protected for obvious reasons. Instead, teams will look for that second lefty reliever, or a backup catcher, or a spare outfielder, or a long reliever, stuff like that. NL teams might look for a veteran hitter to bring off the bench, someone they can hide on their roster all season. Last year, the Yanks lost four players in Major League portion of the R5D, plus two more in the Triple-A phase.

This year, I count no fewer than 37 players in the Yanks’ organization that are R5D eligible. Chances are it’s more, but it can be tough to figure out if some of the international signees are eligible. Now 37 seems like a big number, and it is, but relax, most of them are organizational players that have no business being protected. That said, the Yanks still have some tough decisions to make regarding who’ll protect and who they’ll leave exposed.

Before we get into who they should and shouldn’t protect, we first need to figure out what the 40-man roster situation looks like. As of today, there are 38 players on the 40-man. Brian Cashman has said he plans on “taking it slow” this offseason, so we can assume the Yanks will let all of their free agents hit the market. That frees up seven spots (Damon, Hairston, Hinske, Matsui, Molina, Nady, Pettitte), and the Yanks could easily free up another one by cutting ties with Shelley Duncan the same way they did with Freddy Guzman and Josh Towers.

It looks like Brian Bruney will be back next year (grrr), but not Chien-Ming Wang. That’s another open spot. Jon Albaladejo, Chris Garcia, and Edwar Ramirez all have options left, but I bet at least one (Edwar) goes because they’re easily replaceable. That’s another spot. Juan Miranda qualifies for a fourth option, and he’s worth keeping around.   All told, that would be eleven open spots on the 40-man, but remember that six of those spots will have to be used on replacements for Damon, Hairston, Hinske, Matsui, and Pettitte (Frankie Cervelli replaces Molina, and he’s already on the 40-man), plus assume one more spot for fungibility. That would give the Yanks four spots to use for protecting R5D eligible players.

Three of those four spots unquestionably will be used to protect Austin Jackson, Ivan Nova, and Kevin Russo. Jackson is the organization’s top outfield prospect, and if the Nationals didn’t take him with the first pick of the R5D, the Pirates would gobble him up with the second. Nova was selected but returned by the Padres last year, and the Yanks wouldn’t be so lucky again after his breakout season. Russo is capable of playing five (probably six) positions, and wOBA‘d .371 in Triple-A next year. That’s a guy you keep.

So that leaves one more spot, and about eight players worthy of being considered for protection. Let’s break ‘em down one by one after the jump.

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