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The field is set, post positions are out and we’re just two days away from the 137th Run for the Roses at Churchill Downs. It’s been more than six years since the good Dr. Gonzo kicked the bucket, but you’ve got to think he would love a field as decadent and depraved as the twenty horses that will be lining up on Saturday for an antiquated event that has been running since the era of Reconstruction following the Civil War.

Nobody has really been able to plunk down one horse that truly exudes that aura of winner. None have been so dominant that they beg for an absurd no-money betting line. The luck of the draw (and post positions) have set this race up so that we could easily see another “longshot” in the winner’s circle. But the longshot will be the horse, not the jockey steering him…

In general the field is watered, with horses like The Factor and Toby’s Corner coming up unable to race in the Derby this year. A largely level crop of 3-year-old horses arrives in Louisville for the start of Triple Crown season. And assessing who is going to win is going to be even trickier than usual as we tick down the seconds before the 2:00pm start of NBC’s television coverage on Saturday.

First we need to break down the field, see who is riding which mount and how these horses have done coming into the race. After we investigate the chances of each of the twenty steeds, I’ll offer my predictions for who will emerge victorious. So let’s dive right in and get to it, because the juleps will be flowing soon enough that I can taste ‘em…

1. Archarcharch (Trainer: William Fires — Jockey: Jon Court — 10-1 line)

•  1⅛ Arkansas Derby – winner (4/16)
• 1⅟₁₆ Rebel – 3rd (3/19)
• 1m Southwest – winner (2/21)

Archarcharch might be the best horse to come out of the midwest right now, based out of Arkansas’ Oaklawn Park and the winner of that track’s Arkansas Derby over more highly-rated Nehro just three weeks ago. But several questions remain, including how veteran jockey Jon Court will perform in what will be his first Derby mount in a three-decade career. He got an unlucky draw by being slotted right against the rail, prime position for most jockeys to get bottlenecked in the first few furlongs and lose position permanently. A high-strung horse, he barely won the Arkansas Derby at the wire and would’ve been passed easily by Nehro had the race gone a tenth furlong. At a prime post this horse had a chance, but fate did Fires and his crew no favors for this Derby.

2. Brilliant Speed (Trainer: Tom Albertrani — Jockey: Joel Rosario – 30-1 line)

• 1⅛ Blue Grass Stakes — winner (4/16)

A half-brother of the ill-fated Kentucky Derby winner Barbaro, Brilliant Speed nosed out a victory over Twinspired in the Blue Grass Stakes at Keeneland and was bred to peak at this time of year. But with little race experience ahead of Derby post, will the horse be battle-tested enough to fend off the field? Jockey Joel Rosario has also been spending a lot of time focusing on Dubawi Heights on the west coast, most recently racing the filly in the Wilshire Handicap to victory. He did ride Make Music For Me to 4th place in his first-ever Derby last year, though, so Rosario is definitely wily enough to challenge for the top three places this weekend. But just like Archarcharch, he might’ve been doomed by start position so near the rail.

3. Twice the Appeal (Trainer: Jeff Bonde — Jockey: Calvin Borel – 20-1 line)

•  1⅛ Sunland Derby — winner (3/27)

For most jockeys, getting a post position in the first half-dozen spots from the rail is an ominous sign that things just aren’t turning their way. For Calvin Borel, who in the past five years has been damn near automatic at Churchill Downs, the rail is right where he loves to race. Having won three of the past four editions of the Kentucky Derby (Street Sense in 2007, Mine That Bird in 2009 and Super Saver in 2010) and completed the Oaks/Derby double in 2009 (with Rachel Alexandra in the Oaks and Mine That Bird in the Derby), Borel might just be the most accomplished big-race jockey in Churchill Downs history. Twice the Appeal is a horse who has yet to truly get tested, and Borel is the one jockey who can nurse the best potential out of this half-brother of Closing Argument (2005 Derby runner-up).

4. Stay Thirsty (Trainer: Todd Pletcher — Jockey: Ramon Dominguez – 20-1 line)

• 1⅛ Florida Derby — 7th (4/3)
• 1⅟₁₆ Gotham Stakes – winner (3/5)
• 1⅟₁₆ BC Juvenile — 5th (11/6)
• 7F Hopeful – 2nd (9/6)

Todd Pletcher was 0-for-23 before Super Saver surprised the field to take last year’s Kentucky Derby for the trainer’s first-ever face time in the winner’s circle. This time around he is pinning his hopes on a horse that has posted mixed results at best throughout the past six months. At 9 furlongs the horse first faltered at the Breeders’ Cup Juvenile, finishing well back of fellow stablemate Uncle Mo in 5th, before returning four months later to surprise by 3¼ lengths at Aqueduct for the Gotham Stakes. The Florida Derby sent expectations back to earth, as jockey Ramon Dominguez drove the horse in seventh behind fellow derby entrants Dialed In, Shackleford and Soldat. Son of former Preakness winner Bernardini, Stay Thirsty has yet to exhibit his sire’s finishing speed.

5. Decisive Moment (Trainer: Juan Arias — Jockey: Kerwin Clark – 30-1 line)

• 1⅛ Spiral — 2nd (3/26)
• 1⅟₁₆ Risen Star — 5th (2/19)
• 1⅛ Delta Downs Jackpot — 2nd (11/20)

Despite notching just one career stakes victory (in the one-mile Jean Lafitte at Delta Downs in January), the horse has yet to really exhibit any sort of killer instinct. The grandsire of legendary sire Storm Cat, Decisive Moment is a consistent if unspectacular horse. His jockey, Kerwin Clark, will be getting his first-ever opportunity in the Kentucky Derby. So, like with Jon Court on Archarcharch, we have to wonder if a less-than-favorable post position (though not nearly as bad as the #1 post) and inexperience at the track will be too much to overcome for this Juan Arias-trained horse.

6. Comma To The Top (Trainer: Peter Miller — Jockey: Patrick Valenzuela – 30-1 line)

• 1⅛ Santa Anita Derby — 2nd (4/9)
• 1⅟₁₆ San Felipe — 4th (3/12)
• 1⅛ El Camino Real Derby — 4th (2/12)
• 1⅟₁₆ CashCall Futurity — winner (12/18)
• 1m Generous — winner (11/27)
• 6.5F Best Pal — 4th (8/8)

Few of the Derby horses entered in this 2011 field have raced as much as Comma to the Top, the Peter Miller-trained horse that has gone out for 13 races in his career. The gelding has slowly been improving his speed despite failing to take a win in the new year, and at the sixth post jockey Patrick Valenzuela should be far enough from the post to keep a solid line through the first six furlongs as the race sets up. With one of the fastest top Beyer Speed Figures in the field, Comma to the Top has the top-end ability to surprise a wide-open field.

7. Pants On Fire (Trainer: Kelly Breen — Jockey: Anna Napravnik – 20-1 line)

• 1⅛ Louisiana Derby — winner (3/26)
• 1⅟₁₆ Risen Star — 6th (2/19)
• 1m40y Lecomte — 2nd (1/22)

The Louisiana Derby winner over fellow Derby entrants Nehro and Mucho Macho Man, Pants on Fire recovered from an uninspiring Risen Star Stakes to claim the $1 million stakes race in New Orleans to announce its darkhorse intentions at Churchill Downs. With Anna Napravnik — at 23 one of the fastest-rising jockeys in horse racing and a former money winner at Pimlico — aboard, the horse has steadily improved ahead of the Derby. But with trouble maintaining a solid pace beyond eight furlongs, it remains to be seen if the victory in Louisiana was an aberration or a sign that the stables have found the right racing style for this horse. With horses as heralded as Storm Cat and Seattle Slew in his lineage, Pants On Fire has the pedigree to make some noise in Louisville.

8. Dialed In (Trainer: Nick Zito — Jockey: Julien Leparoux – 4-1 line)

• 1⅛ Florida Derby — winner (4/3)
• 1m Holy Bull — winner (1/30)

The odds-on favorite in the 137th running of the Kentucky Derby, Dialed In has won both his major races this season. Once gates were assigned, Zito’s entry was blessed with the #8 post position, a prime place to break out of the gate — not too far outside, but far enough from the rail to be the one doing the bottlenecking instead of getting bottlenecked. And jockey Julien Leparoux is no stranger to success at Churchill Downs. On 27 June 2007 he won six straight races, just the fifth jockey in history to perform such a feat at the racetrack. He one-bettered his personal best when he tied the track record with seven straight wins on 11 November 2008. If Leparoux rides this course like he’s capable, Zito might just have his long-sought third Derby victor after winning two in quick succession in 1991 and 1994.

9. Derby Kitten (Trainer: Mike Maker — Jockey: Javier Castellano — 30-1 line)

• 1⅟₁₆ Lexington — winner (4/23)

 The 30-1 longshot has improved his speed figures in every start since the calendar turned to 2011, peaking with his victory two weekends ago in the 9-furlong Lexington Stakes at Keeneland. Two black marks against the horse’s chances at Churchill Downs are its lack of major stakes racing in 2011 and the chance that improving speed figures might be a matter of synthetic track surfaces more than the horse’s physical maturation. (Derby Kitten’s one dirt race last fall ended with the steed out of the money.) With former Preakness winner Javier Castellano in the saddle, this horse is definitely a longshot… but at least it is a longshot that has been given every conceivable variable in its favor to yield the best possible chances of success.

10. Twinspired (Trainer: Mike Maker — Jockey: Mike Smith – 30-1 line)

• 1⅛ Blue Grass Stakes — 2nd (4/16)
• 1⅛ Spiral — 3rd (3/26)

Mike Maker’s second horse in the race will be running alongside Derby Kitten with another legendary jockey on his back. Smith, the 2005 Kentucky Derby winner aboard 50-1 longshot Giacomo, has the skills to steer lesser-heralded mounts to podium placings. On Twinspired he finished right behind Brilliant Speed in the Blue Grass Stakes; in the Spiral he was right behind Animal Kingtom and Decisive Moment. This horse, under Smith’s guidance, is in a prime post position to challenge for one of the payoff positions. But with so little dirt experience (one of eight career races, finishing 8th in the only outing) the rainy conditions don’t augur well for this horses chances to steal away victory.

11. Master of Hounds (Trainer: Aidan O’Brien — Jockey: Garrett Gomez — 30-1 line)

• 1³/₁₆ UAE Derby — 2nd (3/26)
• 1m BC Juvenile — 6th (11/6)
• 1m Racing Post Trophy — 3rd (10/23)

With this horse’s only race of 2011 having been a half a world away in Dubai, on the synthetic turf of Meydan Racecourse, the biggest questions facing Master of Hounds are race fitness and surface familiarity. Since the Breeder’s Cup Juvenile, Aidan O’Brien has kept this horse on the shelf for most of the winter and spring racing season. Never has the son of Kingmambo (who also sired 1999 Belmont Stakes winner Lemon Drop Kid) raced on dirt, and Churchill Downs is a hell of a place to familiarize a horse with the surface. Garrett Gomez has the experience if Master of Hounds is at top speed, but luck has never been on the jockey’s side in any of the Triple Crown races. These odds might be too long once again.

12. Santiva (Trainer: Eddie Kenneally — Jockey: Shaun Bridgmohan – 30-1 line)

• 1⅛ Blue Grass Stakes — 9th (4/16)
• 1⅟₁₆ Risen Star — 2nd (2/19)
• 1⅟₁₆ Kentucky Jockey Club — winner (11/27)
• 1⅟₁₆ Breeders’ Futurity — 2nd (10/9)

If recent history holds, this winner of the 2010 Kentucky Jockey Club race at Churchill Downs will follow Super Saver into the winner’s circle at the big race. In reality this Storm Cat descendent will probably be lucky just to get in the money, having faded in recent months. Everything looked promising before the horse increased to a full 9 furlongs at the Blue Grass Stakes, fading horribly to finish ninth against a field that included Brilliant Speed and Twinspired. Bridgmohan, the first Jamaican ever to race in the Kentucky Derby, might find himself under a flagging horse in the final two furlongs.

13. Mucho Macho Man (Trainer: Kathy Ritvo — Jockey: Rajiv Maragh — 12-1 line)

• 1⅛ Louisiana Derby – 3rd (3/26)
• 1⅟₁₆ Risen Star — winner (2/19)
• 1m Holy Bull — 4th (1/30)
• 1⅛ Remsen – 2nd (11/27)
• 1m Nashua – 2nd (11/6)

The big question facing Mucho Macho Man, like so many horses in the twenty-strong field at Churchill Downs, is stamina. The horse has little in his lineage that would inspire confidence in his chances at ten furlongs, but with Mucho Macho Man having acquitted himself at nine furlongs respectably twice we might be led to overlook pedigree — especially in a field that by and large faces as many questions. In finishing third behind Pants On Fire and Nehro as the favorite at the Louisiana Derby the Ritvo-trained horse fell largely off the radar, but the horse offers good value as a show option in trifectas.

14. Shackleford (Trainer: Dale Romans — Jockey: Jesus Castanon – 12-1 line)

• 1⅛ Florida Derby — 2nd (4/3)
• 1⅛ Fountain of Youth – 5th (2/26)

The horse that lost by a head at the wire to Derby favorite Dialed In in the Florida Derby after setting the pace most of the way, Shackleford should scare away a lot of bettors after fading horribly with a 14-second final furlong. A race run nearly as fast off the front as the Kentucky Derby usually is could be the death knell for a front-runner like Shackleford. The betting line would indicate a horse with the potential closing ability, but Dale Romans’ steed has been anything but a closer. A favorable post position and a few lucky breaks could put him in the money, but Shackleford seems unlikely to seriously contend.

15. Midnight Interlude (Trainer: Bob Baffert — Jockey: Victor Espinoza – 10-1 line)

• 1⅛ Santa Anita Derby — winner (4/9)

Few trainers in horse racing have experienced so much success on the biggest stages in the sport as Bob Baffert. A three-time Kentucky Derby-winning trainer, Baffert brings the Santa Anita Derby winner out to Churchill Downs to test one of the west coast’s best horses against the field. Debuting only on January 29th this year, Midnight Interlude is a lightly-raced horse that might yet have more speed potential in its tank. (The Santa Anita was just the third race overall in the horse’s career.) Baffert is a hard guy to bet against, but he is essentially fielding his third-choice horse after The Factor and Jaycito both proved incapable of starting this Saturday.

16. Animal Kingdom (Trainer: Graham Motion — Jockey:  Robby Albarado – 30-1 line)

• 1⅛ Spiral — winner (3/26)

Another horse with nary a moment spent in the dirt, Animal Kingdom has the pedigree to be a good horse at ten furlongs but it remains to be seen how he will run in the much of Churchill Downs. With a win over Decisive Moment and Twinspired in the Spiral Stakes, jockey Alan Garcia showed that he is capable of getting the best out of his mount. Unfortunately Garcia will be riding Soldat, one gate over, while Robby Albarado slides his saddle over. The horse is capable fo turning up the speed at distance, but with nothing in his pedigree or his experience to suggest he is a capable dirt racer the surface is the big question mark against him. The odds line seems entirely fair for a horse that, like Midnight Interlude beside him, is lightly-raced and has even less dirt training in his history.

17. Soldat (Trainer: Kiaran McLaughlin — Jockey: Alan Garcia – 12-1 line)

• 1⅛ Florida Derby — 5th (4/3)
• 1⅛ Fountain of Youth – winner (2/26)
• 1m BC Juvenile — 2nd (11/6)
• 1⅟₁₆ Pilgrim — 2nd (10/3)

Soldat has matured into a horse that showed great potential at nine furlongs when he won the Fountain of Youth against a field that included Shackleford on February 26. But then he went down to the Florida Derby and finished fifth, well behind Dialed In and Shackleford and ahead only of Stay Thirsty as far as the Derby mounts amongst the field. Alan Garcia, a former winner of the UAE Derby in Dubai, has major potential as a jockey but is riding a new horse after Albarado took over jockeying for Animal Kingdom. A half-brother of Baffert’s withdrawn contender The Factor, Soldat has the pedigree to suggest he might sneak up on the field, but recent form makes it a less-certain bet.

18. Uncle Mo (Trainer: Todd Pletcher — Jockey: John Velazquez – 9-2 line)

• 1⅛ Wood Memorial — 3rd (4/9)
• 1m Timely Writer – winner (3/12)
• 1m BC Juvenile — winner (11/6)
• 1m Champagne — winner (10/9)
• 6F Maiden special weight – winner (8/28)

Before being upset by Toby’s Corner at the Wood Memorial, Uncle Mo was on pace to be the overwhelming favorite heading into Triple Crown season. Now, with a gastrointestinal infection ailing the horse, it is unknown whether he will actually step into the #18 gate when the horses post on Saturday. Todd Pletcher has announced the horse is still 50-50 as of Thursday. If he goes, 2007 Belmont Stakes winner John Velasquez could be riding his best shot at a Derby winner in a long career of racing. And Pletcher, who only last year won his first Derby, could have a realistic chance at going back to back after missing out with all of his first 23 entries.

19. Nehro (Trainer: Steve Asmussen — Jockey: Corey Nakatani – 6-1 line)

• 1⅛ Arkansas Derby – 2nd (4/16)
• 1⅛ Louisiana Derby – 2nd (3/26)

The runner-up to Pants On Fire at the Louisiana Derby and to Archarcharch at the Arkansas Derby, Steve Asmussen brings one of the most fascinating horses to the paddock at Churchill Downs. Nehro has a strong pedigree that includes Seattle Slew and Mineshaft, and has shown great consistency at nine furlongs that could easily transfer through the tenth in the Kentucky Derby. Drawing a wide post position could harm the horse’s chances of finding a prime spot in the pack out of the gate, but few of the other horses have shown consistent ability at longer distances. Especially if Uncle Mo fails to go on Saturday, Nehro will be one of the top three horses in the betting… and probably on the track as well.

20. Watch Me Go (Trainer: Kathleen O’Connell — Jockey: Rafael Bejarano – 50-1 line)

• 1⅛ Illinois Derby – 6th (4/9)
• 1⅟₁₆ Tampa Bay Derby — winner (3/12)
• 1⅟₁₆ Sam Davis – 3rd (2/12)

The honors of biggest longshot in the field go to the horse starting out widest from the rail, the 50-1 Watch Me Go was an improbably winner at 8.5 furlongs in Tampa Bay when he won by a neck at 43-1 odds. Without any contests against anyone else in the Derby field, Watch Me Go is a largely untested horse that has raced beyond its expectations to even land one of the final 20 spots in this race. Merely making it here is a victory in itself, and a top-five finish is probably the outside best that Kathleen O’Connell and jockey Rafael Bejarano can hope for this Saturday.

So what does all of this mean? Who do I see as the favorites in this field, the best values… and who, if I were to plunk down for a trifecta bet, would I have in the win, place and show positions?

It’s quite simple. With such an undistinguished field, one with question marks at basically every post position, the likelihood that the jockey is going to make the difference on Saturday is greater than in most years. And that’s why a horse like Twice the Appeal holds so much appeal — with a jockey that knows Churchill Downs more intimately and has experienced more success on the track than all the other riders in the field combined, Jeff Bonde might just have stumbled into the best of luck as he brings the first horse he’s ever entered in the Derby to Louisville.

The potential and the position granted to a horse like Dialed In is too much to pass up, though Borel will outsmart Leparoux to the finish. Zito will once again come oh-so-close to a third Derby to equal Bob Baffert, but will miss out again. And charging up behind will be the horse starting right inside Dialed In, Louisiana Derby winner Pants On Fire. There’s something about Rosie Napravnik that inspires confidence, a strong-willed youngster and a woman to boot to give the story extra appeal. And she’s proven her mettle against some strong fields aboard her mount. 3-8-7, mark it now, that’s who I like in this Derby:

• WIN: Twice the Appeal (Borel)
• PLACE: Dialed In (Leparoux)
• SHOW: Pants On Fire (Napravnik)

Should it happen, Borel will extend on his already-prodigious history with a third consecutive Derby victory and fourth in five years, unprecedented marks both. Bank on history being written when the horses are released for the fastest two minutes in sports on Saturday afternoon…