Geldings almost never win the Kentucky Derby, although whether this is because there are so few of them trying (something for sports statisticians to work on) or because the lack of testicles is an even bigger handicap than it seems, I am not sure. Vagrant in 1876, Apollo in 1882, Old Rosebud in 1914, Exterminator in 1918, Paul Jones in 1920, Clyde Van Dusen in 1929, and Funny Cide in 2003 are the only other geldings to win the Run for the Roses.

Macbeth II was a bay gelding bred by Rufus Lisle and born in Kentucky in 1885. The horse was owned by Chicago Stable and trained by John Campbell.1

In May of his third year, Macbeth II was one of seven horses competing in the Kentucky Derby. He carried 115 pounds, including his jockey George Covington, who only made this one appearance in the now-famous race. At post time, the odds were 6-1 on the gelding.1,2

-------------------------------------------------------------------------
         |                  |               | Macaroni by Sweetmeat 
         |                  | Macaroon      |                         
         |                  |               | Songstress    
         | Macduff          |               |                            
         |                  |               | King Ernest      
         |                  | Jersey Lass   |                 
         |                  |               | Jersey Belle
Macbeth II -----------------------------------------------------------  
         |                  |               | Lexington        
         |                  | Gilroy        |
         |                  |               | Magnolia
         | Agnes            |               | 
         |                  |               | Star Davis    
         |                  | Laura Bruce   |     
         |                  |               | Alida   
------------------------------------------------------------------------2    

It was overcast, but not wet, on May 14 - Derby Day - 1888. The high temperature was only 56 F.3 The track was rated fast as the seven contenters took their places. According to the official race report, Macbeth II did not seem to be a contender until midway down the stretch. The Chevalier, ridden by Isaac Lewis who had won the 1887 Derby aboard Montrose, took the early lead, but gave way to Col. Zeb Ward at the first quarter. Gallifet, the betting favorite, went to the front at the turn, but Macbeth II "hit high gear midstretch." He won by a length with a time of 2:38.25 and earned $4740.1,2 Gallifet was second, White third, and then the order of finish was Alexandria, The Chevalier, Autocrat, and Col. Zeb Ward.

Macbeth II's career was long and relatively successful. Being a gelding, his only income came from finishing in the money. During his career, Macbeth II made 106 starts. He won 25 races, finished second 21 times, and was third fourteen times. His total earnings were $22,170. 4

Notes:
1. The Blood Horse, http://tcm.bloodhorse.com
2. The Kentucky Derby, http://www.kentuckyderby.com
3. NOAA, http://www.crh.noaa.gov/lmk/climate/derby.txt
4. http://members.fortunecity.com/spiletta42/files2.html