He's This Year's Dollar Bill But Who Was Dollar Bill?

“He’s this year’s Dollar Bill” is one of the more popular insults levied at Kentucky Derby contenders on the Triple Crown trail, and this year’s path seems to have more Dollar Bill’s than a bachelor party.

I’ve already declared both Mor Spirit and Mo Tom this year’s Dollar Bills on the strength of their cachet among some Kentucky Derby prognosticators despite the weakness of their last two prep races.

Mo Tom, Mor Spirit not for moi https://t.co/YerYvRqkdK

— Ed DeRosa (@EJXD2) March 28, 2016

Mor Spirit seems the type that looks like he’s going to find another gear and pass everyone but won’t while Mo Tom has run out of excuses with me as he keeps running into horses.

But before there were horses like Dollar Bill, there was Dollar Bill himself, a 1998 Peaks And Valleys colt who was the 6.6-to-1 second choice in the 2001 Kentucky Derby. He finished 15^th in the race won by Monarchos then lost to eventual Horse of the Year and beaten Kentucky Derby favorite Point Given in his next three starts: the Preakness, Belmont, and Travers Stakes (we grant that part of the reason Dollar Bill was overbet in the Derby was because of jockey Pat Day).

After winning consecutive stakes to close his two- and open his three-year-old seasons, Dollar Bill came into the Kentucky Derby off a fourth-place finish as the 17-to-10 favorite in the Louisiana Derby where he “clipped heels” and “stumbled” and a third-place finish as the 11-to-5 favorite in the Blue Grass Stakes where he “bumped start.”

“The worst trip he had was in the Louisiana Derby,” said Dallas Stewart, who trained Dollar Bill for Gary & Mary West. “He should have won that race and maybe some others.

“Some of it is just racing luck, and it seemed like bad luck found him most of his career. I hated to see it because I loved the horse and wanted him to get that big win.”

After winning the 2000 Kentucky Jockey Club and 2001 Risen Star Stakes in consecutive starts, Dollar Bill was winless in 15 stakes tries beginning with the Louisiana Derby and ending with the Suburban Handicap. His lone win in that stretch came in his four-year-old debut in an allowance race at Fair Grounds that he used as a prep for the Oaklawn Handicap.

“He was a sweet horse who deserved a clear shot, and he just never seemed to get it,” Stewart said.

Dollar Bill earned $1,225,546 after having won 4 of 22 starts over four seasons. He died in summer 2004 after foundering and before he was able to begin a stallion career.

So comparing a horse to Dollar Bill indicates three things: 1. The horse has some talent, 2. He has a penchant for trouble, and 3. He’s likely to be overbet.