The first Saturday of May is upon us as celebrities, athletes, and common folk descend on venerable Churchill Downs to witness the fastest 2 minutes in sports. Instagram will be flooded with vastly different perspectives of the festivities from Millionaires Row to shenanigans consuming the infield all under the watchful of eye of the Twin Spires. For those newly initiated to Riders Up! this space is analogous to a Christmas card so we’ll hang out in the paddock before turning to My Old Kentucky Home with the central intention of this annual anthology.
Pinch me. I recently passed 2 years working for a book company (also known as Amazon) which has afforded me the opportunity to author my own narrative as I've found a few blank pages. Fortunate to be part of the Amazon Web Services (AWS) rocket ship allowing me to grow equally professionally and personally serving startup/venture capital ecosystem in addition to driving global blockchain initiatives. Always expanding my comfort zone is my life maxim. Amazon nurtures my life maxim to always push my comfort zone in working backwards from our customers and learning from an insanely talented team.

Speaking of The Masters. Welcome back Tiger, golf clap on 15 and 81. It was powerful to see him regroup after self-inflicted wounds and touching to witness him share an intimate moment with his kids/mom in the same greenside location he hugged it out with his father/mother 22 years prior after his first. Another hat tip to NFL GOATs, Tom Brady and Bill Belichick with their 6th Lombardi defeating the organization they won their first against. Simply ridiculously awesome – he’s 41 albeit 58 year old Jon Court will be in the irons of Long Range Toddy for the Derby. Go Sharks. Prediction, Jumbo will play his original team in the finals and hoist Lord Stanley then skate off to a local golf course with a future date in a hallowed Hall. Sports world is full of these coming full circle themes – Where’s Rinaldi or better yet Marty Smith?
Given my prior diatribe, with high probability the winner will come from the Front (F) or Stalking (S) position. Data dictates Closers (C) used to occur more frequently, with chances much slimmer now.
Pedigree
WIN 17 Roadster
Elle (9 going on 29 in the best way) and James (12) impress me with their burgeoning intelligence, curiosity, and passion to follow their developing dreams. Elle debuted in her school play (Mary Poppins / "just" off Broadway) and now has aspirations to replace Ellen in the “near” future with The Elle Show – she’s disappointed Ellen has a minimum age of 14 for the audience. To beat that restriction Elle envisions being invited as show guest. Meanwhile James continues to excel with video games so much he has found his way to YouTube lore playing with Pro Gamers applauded his skills while having little clue his age. Twitch Channel here we come.

I visited Tel Aviv for work and a personal side excursion to Jerusalem/Bethlehem. Wow! Captivated by the religious history in reliving many parables while astonished how so many religions literally touch each other peacefully. Once again I made the pilgrimage to the cathedral of golf in Augusta National. I indoctrinated my good friend Ryan McCalley on his maiden voyage around Amen Corner, Rosebud, and golf shop for a Tuesday practice round. We fortuitously met Bel Air Country Club icon Eddie Merrins and his son while seeing nearly every top player in the world. Pro tip always check the weather a few weeks out and use it to your advantage – SCORE!! Ryan recently left the craziness of Silicon Valley for Savannah/Hilton Head area with his expecting wife and 2 adorable kids which affords me a reason to venture to their beautiful property and chase a little white Titleist.


Why does Game of Thrones have to end? Yes, I would have typed GoT, however my parents would have zero clue on that reference. Now it improves to 9% on low side and 26% on high. Billions is always on point weaving the trading world with reality. Who knows maybe there’s a future in a new show for me – Crypto anyone?
In Memoriam. On March 18 Riders Up! 2009 Derby Selection Pioneerof the Nile died of a heart attack. He finished 2nd to 50-1 longshot Mine That Bird courtesy of Calvin Bo”rail.” Most recently Pioneerof the Nile was receiving $110k stud fees after his son American Pharoah won the 12th Triple Crown in 2015. Purchased for $290k his career earnings were $1.63MM and he stood in stud from 2010 up until his death. In other news, recently the track at Santa Anita has been through a devastating season as 23 horses have died mainly due to training injuries. Santa Anita was closed for all of March losing a typical Derby prep in the San Felipe Stakes. It reopened for the Santa Anita Derby won by Roadster with Game Winner coming in second on a safer/slower track.
Finally, every year my inspiration for penning this compilation traces to my parents – I scored on pedigree. They introduced me to horse racing at an impressionable age ferrying my sister, brother, and me to Canterbury Downs. Love you Mom, Dad, Tracy, Jason, and hug to my kids. Enough with our time in the paddock, Riders Up!
A Changing Race
Handicapping the Derby has significantly changed due to Derby Point System being instituted (2013) as it moved from Graded Stakes Earnings. Since the change six straight favorites have won. This is the longest run of favorites in Derby history mixed with 2 Triple Crown winners after a 37 year drought. The average odds of the winner have been $3.43-1 the past 6 years. The old system has yielded average odds of $16.05-1. Personally, its sacrilege as a handicapper to select the favorite every year, hence the dry spell with Derby Winners recently.
Since Riders UP! choice Orb’s win from well off the pace (16th at half-mile), each subsequent winner has sat 2nd or 3rd in the crowded field at the half-mile marker and never lower throughout race. In contrast, from 2000 thru 2012, only War Emblem and Funny Cide won from better than fourth at the half-mile point, with six winners coming from 12th or farther back. Surprisingly, from 2000-2012, the average half-mile time of the leader was 46.39, while from 2013-2018 that time was slightly faster at 46.34. When examining the median half-mile times, the recent races were also faster (46.15 vs. 46.23). None of the data suggest that there has been a significant difference in the half-mile pace of the Derby since the rule changes.
The chart below illustrates recent Derby history with Derby Points System Rank and winner’s position at half-mile.
Year
|
½ Mile
|
Derby Winner
|
Place
|
Show
|
2018
|
2nd
|
Justify (8)*
|
Good Magic (2)
|
Audible (3)
|
2017
|
2nd
|
Always Dreaming (6)
|
Lookin At Lee (23)
|
Battle of Midway (16)
|
2016
|
2nd
|
Nyquist (2)
|
Exaggerator (3)
|
Gun Runner (1)
|
2015
|
3rd
|
American Pharoah (4)*
|
Firing Line (12)
|
Dortmund (2)
|
2014
|
3rd
|
California Chrome (1)
|
Commanding Curve (21)
|
Danza (5)
|
2013
|
16th
|
Orb (1)
|
Golden Soul (19)
|
Revolutionary (6)
|
Intriguing Stats
· Last to Lose @ Age 3: Last 7 Derby winners were unbeaten at 3. Since Super Saver (2010) all Derby winners had won previous start. Animal Kingdom (2011) was the last Derby winner to lose at age 3. He failed in a Gulfstream allowance test, but returned to win the Spiral in his final prep.
· Subdued Superfecta: Not only have favorites won the last 6 Derby renewals, but 18 of the 24 superfecta slots have been dominated by horses at 10-1 odds or less.
· 2 Year Old Champ: The last 4 enjoyed strong Derby showings: American Pharoah (2015) won Triple Crown; Nyquist (2016) won Derby; Classic Empire (2017) 4th; Good Magic (2018) 2nd. Game Winner was this crop’s 2-Year Old Champion.
· Winning Length: 13 consecutive Derbies have been decided by a length or more. The last close shave came with Giacomo’s half-length score (2005). The last photo finish was Charismatic’s 1999 victory by a neck.
· Trainer: If Bob Baffert wins another Derby, he will equal Ben Jones’ record for most victories.
Revealing My Kiper/McShay Derby Draft Board
Derby Entries
|
Record
|
DPS #
|
Beyer
|
Work
|
Strikes
|
Style
|
Pedigree
|
Dosage
|
1 War of Will
|
8-3*-1-1
|
12
|
94*
|
47.3
|
1 – 5
|
F/m
|
Yes
|
1.72
|
2 Tax*
|
5-2*-2-1
|
14
|
96*
|
47.4
|
2 – 6,9
|
S/?
|
Yes
|
1.56
|
3 By My Standards
|
*5-2-2-1
|
6
|
97
|
48.2
|
1 -6
|
S/m
|
?
|
3.00
|
4 Gray Magician
|
8-1*-3-2
|
18
|
80
|
1:00.2
|
2 – 2,3
|
S/-
|
?
|
5.00
|
5 Improbable*
|
5-3*-2-0
|
11
|
99
|
1:00.3
|
3–4,6,7
|
S/?
|
Yes
|
4.23
|
6 Vekoma*
|
*4-3-0-1
|
3
|
97*
|
59.4
|
1 – 6
|
S/?
|
?
|
2.56
|
7 Maximum Security
|
4-4-0-0
|
7
|
102
|
53.4
|
1 – 6
|
F/m
|
?
|
3.00
|
8 Tacitus*
|
4-3-0-0
|
1
|
97
|
1:00.0
|
1 – 6
|
S/m
|
Best
|
3.31
|
9 Plus Que Parfait
|
*7-2-1-2
|
4
|
84*
|
1:02.0
|
1 - 7
|
C/m
|
?
|
2.47
|
10 Cutting Humor
|
*6-2-2-1
|
15
|
95
|
48.0
|
0
|
C/m
|
Yes
|
2.11
|
11 Haikal
|
5-3*-1-1
|
10
|
95*
|
1:01.1
|
2 – 3,6
|
C/m
|
?
|
3.00
|
13 Code of Honor
|
5-2*-1-1
|
9
|
95*
|
46.4
|
1 - 6
|
C/?
|
?
|
0.76
|
14 Win Win Win
|
6-3*-2-1
|
16
|
99*
|
47.3
|
2 – 2,3
|
C/m
|
Yes
|
4.50
|
15 Master Fencer
|
6-2*-2-0
|
20
|
-
|
-
|
3 – 1,2,3
|
C/m
|
?
|
2.50
|
16 Game Winner*
|
6-4*-2-0
|
8
|
97
|
1:27
|
0
|
S/?
|
Yes
|
2.33
|
17 Roadster*
|
4-3-0-1
|
5
|
98
|
1:13
|
2 – 1,6
|
S/?
|
Yes
|
2.60
|
18 Long Range Today
|
8-4*-1-1
|
13
|
95*
|
47.4
|
3 -3,4,5
|
C/-
|
Yes
|
4.33
|
19 Spinoff*
|
4-2*-1-1
|
19
|
95
|
1:00.3
|
3 – 2,4,6
|
F/m
|
Yes
|
2.78
|
20 Country House
|
6-1*-2-1
|
17
|
91
|
1:00.0
|
2 – 2,3
|
C/-
|
Yes
|
2.69
|
21 Bodexpress
|
5-M*-3-0
|
21
|
96
|
1:03.0
|
2 - 2,6
|
S/-
|
Yes
|
8.33
|
Derby Entries with *: 3rd race off layoff, building foundation, primed.
Record with *before Starts: Has lost as 3 YO, Won last time out
Record with *after Wins: Has lost as 3 YO, Lost last time out
Beyer with *: Last Beyer was not their highest
Pace Scenario/Running Styles/Weather

Weather may also play a factor. Colts who’ve had success in slop have an “m” under Style. Forecast is calling for rain which could impact my betting strategy. War of Will, Tacitus, Maximum Security, Win Win Win have fared well in slop.
Pedigree
Homework complete with AWS SageMaker AI/ML models on who will get the lengthy 1¼ mile. Additionally, I’ve diminished the use of Dosage (4.00 and lower) which formerly was a component to determining Derby winners. Dosage is a ratio of speed over stamina and with distance to run with stamina usually is desired for this length race.
Northern Dancer Line: Omaha Beach, War of Will, By My Standards, Spinoff, Cutting Humor, Haikal, Code of Honor
Mr Prospector Line: Roadster, Game Winner, Vekoma, Gray Magician, Maximum Security, Improbable, Country House
Hail to Reason: Win Win Win, Master Fencer, Tax, Plus Que Parfait
Seattle Slew: Tacitus, Long Range Toddy
Note immortal bloodlines Secretariat can be found in 15 of 20 contenders. Those not included War of Will, Code of Honor, Haikal, Plus Que Parfait, and Country House.
Strikes – Courtesy of Jon White
My analysis has incorporated Jon White’s Strikes System which dates back to 1973 when grading stakes became a standard. It is an amalgamation of factors marrying TACTICAL with HISTORICAL. 38 of the last 46 Kentucky Derby winners have had zero or one strike. Category 6 in this system has diminished in impact, thus it would not preclude me from selecting a 2 strike horse with one being in that category.
Let’s Handicap
20 horse field demands an elimination of equines. Toss are those owners who are purely here for the Mint Juleps to say they had a Derby horse at the Brownstable Brown party. Could Factor are horses that may hit the board that I’m betting against. My Contenders are collection of athletes I expect one to be draped in the Garland of Roses.
Toss (6)
|
Could Factor (6)
|
4 Gray Magician
|
2 Tax*
|
9 Plus Que Parfait
|
6 Vekoma
|
10 Cutting Humor
| |
15 Master Fencer
|
13 Code of Honor
|
18 Long Range Today
|
19 Spinoff*
|
20 Country House
|
AE 21 Bodexpress
|
My Contenders (8)
|
Notes
|
1 War of Will
|
Tough LA Derby. Post position severely hampered chances.
|
3 By My Standards
|
Working Well…Wise Guy pick
|
5 Improbable*
|
Sometimes loses focus, Blinkers on or off? Could win or finish 20th.
|
7 Maximum Security
|
1st race was a $16k claimer. Pace –aided wins in FL Derby. Only horse w/ 2 100 Beyers. Only 1 other horse has a 100 and he scratched.
|
8 Tacitus*
|
Handled adversity gaining great seasoning. 1 horse has won Tampa/Derby double ever & last Wood/Derby double was 1999 (although, Riders Up! Selection Funny Cide was 2nd in Wood/won Derby '03).
|
14 Win Win Win
|
Hockey is in the blood with Hat Trick as his sire – Like in EXOTICS and slop! Training brilliantly.
|
16 Game Winner*
|
Only 2 have won Breeder’s Cup/Derby in 34 years. Could be primed for a big jump. Has not won at Age 3. Will now most likely be favorite ahead of Roadster.
|
17 Roadster*
|
Santa Anita Derby winners have been good in Derby (’12, ’14, ’18 wins). Last 25 Gray colts have lost Derby dating back to 50-1 Giacomo in 2005. Had throat surgery in November to assist breathing. Hasn’t lost since. Henry Ford would be proud.
|
Derby Entries with *: 3rd race off layoff, building foundation, primed.
2019 Selection
Enough with the furlongs of facts. In Kramer speak - Giddy Up! The expected favorite Omaha Beach’s scratch certainly impacted handicapping this race[update - 11 Haikal has also scratched and Mike Smith now riding 13 Code of Honor]. Parity comes to mind with this vintage yielding cases easily made for a handful plus to be draped in roses. Game Winner will most likely be the post time favorite although you could see a couple others push. All 3 Baffert horses (Game Winner, Improbable, and Roadster) are sitting on their 3rd race off a layoff which he hits the board 31% of time – do the math. I love the versatility of Roadster despite being lightly raced (4 trips). He will need to beat the odds of no horses ever winning from PP17, however Omaha Beach/Mike Smith (who chose Omaha over Roadster) defection assists as he now will break from PP16. PP16 was Riders Up! first Derby and original score with Thunder Gulch. I am betting on a big move forward. The battle tested Tacitus (also 3rd race off a layoff) could be sneaky in this race along with a solid 2 year old champion Game Winner, Win Win Win, and Improbable rounding out my top 5. Interestingly, Roadster has not been hyped as much as the other Baffert horses in recent days, please keep it that way. I will most likely (depending on weather) have exotics keying 17 Roadster, 8 Tacitus, 16 Game Winner on top.
WIN 17 Roadster
PLACE 8 Tacitus
SHOW 16 Game Winner
4th 14 Win Win Win
5th 5 Improbable
6th 7 Maximum Security
7th 1 War of Will
8th 3 By My Standards
Please, enjoy your Derby responsibly.
Riders Up! See You in the Winner's Circle!
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