This article contains lore created collaboratively by the Blaseball community. It is just one of many Rumors that we've found in the Interdimensional Rumor Mill. You can find more Rumors about Kennedy Loser at their Rumor Registry.
Kennedy Loser was born Loser Kennedy somewhere in Appalachia. He changed his name and fled to Baltimore, Maryland for undisclosed reasons. His childhood closeness to his grandmother, Velma Kennedy, and her strange fixation on prophecy and apocalyptic imagery led to his eventual closeness to the Olde One and his proclivity for tarot.
Kennedy joined the Baltimore Crabs' original lineup upon their incorporation into what would eventually become the Internet League. He became the close friend and confidante of Combs Duende, the former unofficial team captain, and directly served alongside them in the war against the Olde One. Loser's experience in the fight and association with Duende, as well as shared trauma from the tragedy of the situation, shaped Loser into a sort of team "dad" figure, who many of the other Crabs looked up to for guidance. In a 201X interview with Wow! Blaseball, Tillman Henderson stated that he could "just barely stand" Loser, and that this was "more than [he] could say for the rest of those clowns." Players from both the Crabs and other teams considered Loser's townhouse a sort of neutral zone, where anyone who needed a place to stay could do so with no questions asked.
Transfer to the Immaterial Plane
When Blaseball transitioned to fully Immaterial operation and the Internet League began playing, Loser was among the players whose transfer to the new medium was botched, resulting in a distorted version of themselves. Loser became aware of the entire internet at once, as well as the shared experiences of several alternate versions of himself, and many of his strange behaviors and actions can be explained in light of this influx of information and context. Despite only being twenty-nine years old, Loser developed a reputation as a sort of "old guy" due to his typing style and many quirks.
Career in the Internet League
In the 202X Baltimore Area Blaseball Unearthed article "Who's Best?" Loser was mentioned as one of the contenders for the Best Baltimore Batter award, a niche prize awarded by the publication every year. That year's winner was, of course, Forrest Best, as is spoiled by the article title. Loser slowly rose to prominence as one of the more popular mid-tier Idols for fans, especially as a result of the historic Season 5 elections, but ultimately his ability suffered from several ill-timed blooddrains. When asked about how these blooddrains felt, Loser reportedly stated, "Ouch and Owie!!" but insisted that it hadn't been anyone else's fault, and that this was "just how the Game Goes."
Upon learning that players could be resurrected from the dead, Loser made it his personal goal to eventually, at any cost, locate the Hall of Flame and free the players trapped there, especially Combs Duende and Nora Perez.
The death of Combs Duende had been particularly rough on Loser. Though he did not witness their incineration himself - only seeing the aftermath - the fact that Combs reportedly took an incineration meant for him weighs heavily on his conscience. In a 202X interview with Why is this Happening to my Splort, a Blaseball-focused therapeutic publication, Loser stated that the loss of Combs was a "damn Shame" and that he felt like "We should really Do some thing about these Umires"[sic].
Post-Ascension and Siesta
Loser's early thoughts on the Ascension of the Baltimore Crabs are lost to time, as his primary outlet of communication, his Twitter account, was scooped up by Products, Inc. in the chaos of the transfer of ILB ownership to the Boss following the Season 10 election. Eventually, a rogue intern returned the account to Loser, who had also lost his phone during the ascension. Loser reported that he "hate[d] Solid Chunks," the product which had been extensively advertised on his account since the acquisition of his account by Products, Inc., but was unable to figure out how to remove the cute sloth meme the company had pinned to his page to advertise the product.
By his own admission, Loser suffered greatly from the loss of Sutton Dreamy, Nagomi McDaniel, and Montgomery Bullock to the Hawai'i Fridays, but became fast friends with Evelton McBlase II, who Loser mentored and collaborated with in an effort to stop his schemes and machinations from causing any lasting damage.