This year’s Preakness Stakes figures to be more of a handicapping challenge than any Preakness since 2010. Lookin At Lucky beat Derby winner Super Saver that year. We could see something similar on Saturday with a second or third choice horse like Alwaysmining winning the race. Or, we could see a horse like Win Win Win shrug off his Derby debacle to take the Second Jewel.

Check out cases for and against both Alwaysmining and Win Win Win to take home the Preakness Stakes Trophy on Saturday.

Preakness Stakes Case For & Against Alwaysmining & Win Win Win

Preakness Case for and against Alwaysmining

Alwaysmining might be this year’s wise guy Preakness Stakes horse. He races primarily at Laurel Park, Pimlico’s sister racetrack. He’s trained by Kelly Rubley, not a household name at all. His jockey, Daniel Centeno, primarily rides at Tampa Bay Downs.

He also hasn’t won a graded stakes race during his career. Based on all that, it’s amazing that he’s offering around 6/1 odds in the futures to win on Saturday. The fact he’s attracting so much attention can only mean one thing, professional horseplayers are taking him seriously.

Everyone should be taking Alwaysmining seriously. He broke his maiden last June in his second lifetime race. From there, he went from Laura Wholer’s to Eddie Graham. Kelly Rubley took over Alwaysmining’s training after his third race. Although he failed in his first start with Rubley, he’s been great ever since, running off 6 straight victories.

Alwaysmining should get the perfect trip in the Preakness Stakes. He can track behind likely front runners Warrior’s Charge and Market King, take the lead around the turn and then pull away at the top of the stretch. He’s run faster or as fast as any horse in the race. Not only that, but Alwaysmining has worked great since the Federico Teseo Stakes win.

The lone knock appears to be one of class. He has yet to face horses as good as War of Will and Improbable. Other than that, it’s hard to find reasons why Alwaysmining can’t win the Preakness Stakes on May 18.

Preakness Case for and against Win Win Win

Win Win Win, a Michael Trombetta trained, Hat Trick sired colt hade a terrible trip in the Derby. He had no shot after having to go 4-wide early over the sloppy racetrack. A closer look reveals a major positive, though. Win Win Win provided another strong closing kick. It wasn’t nearly enough because he ran so slow early on in the race, but he did manage to finish in the Top 10.

On Saturday, Win Win Win has a much better chance. The Derby is a free for all if you’re a closer. Unless you get the perfect trip and perfect setup like Orb in 2013, you’re not going to win the Kentucky Derby.

The Preakness Stakes is different. Horses like Win Win Win can take the race because the fields aren’t close to having the same amount of horses. If Win Win Win can get into a good position right away, like he did in the Blue Grass Stakes where he ran much faster early stages, he can pull off the upset.

Like the other closers in the Preakness Stakes, though, Win Win Win is beholden to the pace. Alwaysmining won’t have that issue. Alwaysmining could be the horse to beat, he’s that good. Even though Win Win Win will need some help, he’ll have a shot at the upset if the pace is swift and he gets off to a good start. Both are decent horses to back to win the 2019 Preakness Stakes.