Bored in the Shadowlands

The fellow known as Jon Chess was bored.

Worse, he feared that his patron, the Lord High Admiral Jaina Proudmoore, had lost confidence in him. 

When Jaina had founded the city-state of Theramore after the Battle of Mt. Hyjal, she had found relying on the Stormwind SI:7 organization for intelligence distasteful and worse, tactically unsound. She had an innate distrust of Mathias Shaw, and did not think for a second that Shaw would sacrifice Theramore and its founding ideals the minute it was advantageous for the Alliance in the struggle against the Horde. 

She contacted her family friend Elling Trias, who had run Alliance intelligence before SI:7 was created, and who had retired to build a mercantile empire based on the buying and selling of cheese, and asked for his advice and assistance. Trias agreed that Shaw was not to be trusted, and so Trias recruited a young rogue, fresh out of the Stormwind Orphanage, who had declined to join SI:7, and had survived the refusal. Arranging him to be Trias' traveling mercantile agent, he sent the young rogue to Ravenholdt for advanced training in the Great Game.

Trias had even gifted Jon with the name 'Chess', claiming that Jon thought too much, and needed to be more man of action than to spin contingency after contingency. "Life is not a chess match; sometimes you have to be bold, and take a leap of faith," he had said, and the name acted as a reminder for Jon not to over-think things or hesitate when action was needed

Afterwards Jon established a hoe of sorts in Theramore. When Jaina needed his particular brand of services, from spying to assassination, Jon stood close at hand. He trusted Jainas to be the one to decide if the gains justified the means, and once she made that determination, Jon would accomplish Jaina's objectives,

When Theramore was destroyed and all of Jon's close friends - including, so he believed, Jaina - were killed, Jon's mind fractured after being captured and tortured by the Scarlet Crusade. What came out of it was a splintered mind - Jon Chess, recon scout in Northrend by day,  and the Rook, an amoral assassin by night.

Jaina came back, and quit Dalaran without contacting Jon Ironically it was Genn Graymane who reached out to Jon when Jaina surfaced again to try and re-engage Kul Tiras with the Alliance. Graymane had used Jon's services before - Jon, though not Afflicted, was Gilnean by birth. Jaina was almost in tears when she  saw that Jon had survived Theramore as well, and it was ot long before Jaina found use for a trusted privy agent of cheese.

After the end of the War of Thorns, Jaina was captured by the Mawsworn. Jon sat in Northrend while the Maw Walkers rescued her and spearheaded the struggle against the Jailer, working to rescue Anduin Wrynn. 

Jon had been assigned to assist the Fae of Ardenweald. 

Since then, he had found no dearth of work that needed doing. 

Still, he could not help feeling that he had lost Jaina's confidence.

((Note: I hate Shadowlands, and was close to quitting the game I've played since WoW beta. I am very much looking forward to the next expansion, where Jon's adopted "brother" Rorik Chess gets to shine! But not have Jon angst over something? Unheard of!))