Timothy Sinclair

Captain Timothy Sinclair was a Starfleet officer in the late 24th century. He was the first commanding officer of the USS Pendragon, serving in that capacity from 2379 to 2385.

Early life
Born on June 22, 2341, Timothy Jacob Sinclair was an orphan almost from his first breath. En route to Utopia Planitia, Mars, a shuttlecraft accident resulted in the death of Commander Jacob Sinclair and seriously injured his pregnant wife, Ilanna Sinclair, Daughter of the Seventh House of Betazed. Ilanna was rescued and taken to Christopher's Landing, Titan, where she gave birth to her son, and died.

With no human family, and rejected by the Seventh House, the young Sinclair was taken to Enclave J-12 on Titan, a facility for Federation orphans. As part of an undisclosed "special project," he was raised in virtual isolation, under the tutelage of Dr. Robert Blaisdell.

The wandering years
Sinclair left the Enclave shortly after his fourteenth birthday in 2355, under controversial circumstances. He began traveling around the galaxy, bartering passage for work on freighters. On his travels, he encountered the Orion Syndicate and the Lalairu.

He met Vash while traveling aboard a Lalairu vessel in the Great Rift region. Vash was the first human he had seen in over six months, and as the only humans aboard, they spent much time together. Intrigued by each other, their mutual passion for archaeology turned into a different type of passion altogether, which years later, Vash would remember with fondness, while Sinclair would call it "the second biggest mistake" of his life.

After departing the Lalairu, Vash and Sinclair continued to travel together, forming a partnership that lasted for six months. Half that time was spent among the ancient outposts of the former Tkon Empire. Their partnership disolved when Sinclair realized that Vash was just using him, and took off for the galactic rim.

In late 2357, Sinclair's travels brought him to Belle Terre. While there, he aided Lieutenant Steve Tecklenberg in rescuing colonists from a terrorist attack. Tecklenberg was impressed by Sinclair's resourcefulness and character, and persuaded the young man to join him when he returned to duty on the USS Beachmont after the new year's celebrations.

Academy
Aboard the Beachmont, Sinclair saw a much different view of Starfleet than he was presented with in the Enclave. During that time, the Beachmont picked up survivors from the doomed USS Pegasus and he befriended Ensign William Riker. With the encouragement and assistance of Lieutenant Tecklenberg and Captain Paul Twining, he applied to Starfleet Academy and was accepted.

Reporting for duty at the Academy's San Francisco campus, Sinclair inadvertently got caught in a scuffle with freshman cadet Ben Bartholomew, and both of them were called before the Academy Commandant. The Admiral thought a fitting punishment would be to assign them as not only squadmates, but roommates. The plan worked, and after a period of intense friction, Sinclair became a calming influence on the hot-headed Bartholomew, and while the latter would help to draw Sinclair out of his shell. During their time in Nebula Squadron, the two cadets became the best of friends.

Other friendships that Sinclair had at the Academy included those with Joshua Hofmann, Mark Montgomery, Justin Shive, Jordan Dennis, Antonius Strube and Christopher Durham. Sinclair would maintain most of these friendships for the rest of his life. He likewise maintained a friendship with Steve Tecklenberg, who was reassigned as the field instructor for Nebula Squadron, and became a mentor to Sinclair.

In his junior year, Sinclair was accepted into the undergraduate program at the Advanced Tactical Training Center on Mars. Anthony Strube and Justin Shive were his classmates there.

During his Academy years, Sinclair harbored feelings for his squadmate Mary Barranco but never had the courage to tell her how he felt. Eventually, he was pushed into a romance with another cadet, Jean Brennan, set up by Bartholomew. Though initially reluctant, Sinclair developed feelings for Jean (which were reciprocated), and they married after graduation.

Early career
Ensign Sinclair's first assignment after graduation was as a helmsman on the USS Rutledge, under Captain Benjamin Maxwell. Joining him on the Rutledge was his classmate Chris Durham. On board, Sinclair met Chief Petty Officer Miles O'Brien, who took the young Ensign under his wing.

After less than six months on the Rutledge, Sinclair, O'Brien and Durham were on the away team that responded to the Setlik III massacre. On the surface, the team was caught in a firefight with Cardassian troops. Durham took a disruptor hit for Sinclair, sacrificing his life (and unknown to Sinclair at the time, releasing the Darrum entity from corporeal form).

After Setlik III, Sinclair took leave and returned to Earth. He and Jean moved into his father's ancestral ranch in Colorado. After a month, he returned to duty with the Judge Advocate General's Office while awaiting his next deep space assignment.

In May 2363, Sinclair was assigned to the USS Cerberus as a security officer. While exploring near the galactic rim in January 2364, the Cerberus was attacked by unknown forces, suffered a warp core breach, and was destroyed. Sinclair was among a handful of survivors, waiting in lifepods for three weeks, before being rescued by the USS Potemkin.

Sinclair and the other Cerberus survivors were given a mandatory one-year "cooling down" period. Sinclair returned to the JAG Corps on Earth, and began weekly counseling sessions with Lt. Commander Nan Ross.

Scandalon
After six months on Earth, Sinclair was itching to be out in space again, and that's when Steve Tecklenberg offered him a spot on the USS Scandalon, as a member of the special operations group, the Eagle's Nest Squadron. Sinclair jumped at the chance, and joined Tecklenberg, Bartholomew, Shive and other old friends on the Scandalon, initially serving as a security officer.

In May 2365, Ensigns Toby Moore and Brad Powell were assigned to the Scandalon on Sinclair's recommendation. He had served as a Cadre (upperclassmen supervisor) for them at the Academy. Shortly thereafter, Powell was captured, tortured and killed during a covert assignment. Sinclair blamed himself, as did Toby Moore, who never forgave Sinclair for the death of his best friend, leading to more than twenty years of bitter animosity between the two men.

Next assignments
In October, Sinclair (and Bartholomew) left the Scandalon and joined the crew of the USS Wayfarer.

In September 2366, Sinclair was promoted to full Lieutenant and assigned to the USS Langley as Security Chief. He would remain in that position until the Battle of Wolf 359.

While recovering from his injuries, Starfleet assigned Sinclair as an instructor at the Academy, acting on the recommendation of Admiral Twining. He served as a Field Instructor for Nebula Squadron through the end of the 2368 school year. During and after his assignment at the Academy, Sinclair was sent on a series of covert missions for Starfleet Intelligence.

In the summer of 2368, he was promoted to Lieutenant Commander and assigned as intelligence officer on the USS Sutherland. He served under Captain Timothy Barranco, and once again, with Ben Bartholomew. During his time on the Sutherland, Sinclair would be sent on several special assignments for SI.

In 2371, Sinclair was again promoted (to Commander), and accepted the post of executive officer on the Galaxy class USS Christopher Pike (NCC-72091), under Captain Brady Thornton. He continued to work with Starfleet Intelligence when they required his services.

Wartime service
Sinclair was still serving on the Christopher Pike when Admiral James Leyton staged his coup on Earth. He participated in battle to defend Deep Space 9 from Leyton's assault in late 2372, and witnessed the station's destruction.

He continued to serve on the Chris Pike through the end of the so-called Federation Civil War in January, 2374.


 * In the mainstream universe, Sinclair accepted promotion to Captain in 2374, and took command of the USS Ulysses. He was killed in the Second Battle of Chin'toka in 2375.

Resignation
During the final battle of the Civil War, Sinclair's wife Jean was killed while infiltrating Starfleet Headquarters. Following the cessation of hostilities, Sinclair turned down promotion and resigned his commission, returning to Colorado to raise his twin sons, Jeff and Tyler.

Pendragon
Five years later, Admiral Coleman went to Sinclair, asking him to return to duty and take command of a ship Starfleet Command was sending into the Demilitarized Zone. Sinclair refused, but Coleman talked him into coming aboard the USS Pendragon for her shakedown cruise. After he helped save the ship from sabotage, Sinclair realized the importance of the Pendragon's mission, and accepted Coleman's offer of command (though there were other, more personal reasons involved in his decision).

2379
While at Deep Space 9, Sinclair was reunited with his old friend Miles O'Brien, and with his old rival, Garak. (PDN: "Restoration") When the Pendragon departed for Cardassia Prime, Garak stowed away. Once his presence was revealed, Sinclair allowed him to accompany an away team to the surface, where they discovered that Gul Madred had taken control of the government. (PDN: "Exile") Later, Sinclair, Garak and Jordan Dennis met with Michael Eddington and Akellen Macet for a special edition of The Dennis Report to demonstrate the severity of the situation in the Demilitarized Zone. (PDN: "The Distant Fire"; "Wounded Soldiers")

In September, the Pendragon responded to an automated distress call from the SS Artemis, a colony ship lost in the DMZ in 2374. Tracing the ship's flight path, they found the crash site on Korvair VII and evidence that the ship's crew and passengers had fled in escape pods to evade the Klingons. Following a lead, Sinclair led a team to Eris II, where he and Jason Bartholomew were captured set up by Mortonn and captured by the Tal Shiar. Taken to a secret work camp, Sinclair found the Romulans had abducted Maquis survivors from the Klingon raids, using them as slave labor as part of an invasion plan. Sinclair escaped during interrogation, freed Jason and found Ben Bartholomew among the survivors. They were rescued by the Pendragon. (PDN: "L'Morte d'Maquis"; "Hidden Agendas")

In October, Sinclair was summoned to Betazed by his grandfather, Lord Andrus Kelisen. (PDN: "Heritage") After his return to the Pendragon, he joined Lieutenants Riniker and Svek in tracking down an ancient Vulcan mind-killer. (PDN: "The Forgeman")

After Bartholomew kept stonewalling Counselor Kiley Thoren in her attempts to help him acclimate to civilization again, Thoren came to Sinclair and asked for his help. Through reminiscing about their days at Starfleet Academy, they reconciled. (PDN: "Children of the Burning Heart")

In December, Sinclair and Svek went undercover in the Tal Shiar fleet in order to stop their invasion of Cardassia. During the mission, Svek was killed. Afterwards, Sinclair returned his katra to Vulcan. (PDN: "In Darkness Find Me"; "Twilight's Call")

2380
En route to Emmaus on the Pendragon, Sinclair was visited by the "ghost" of his friend Christopher Durham, who revealed himself as the non-corporeal being, Darrum and warned Sinclair that dark times were ahead. (PDN: "Approaching Emmaus")

While traveling to a conference at Starbase 47, Sinclair's shuttle was attacked by Orion pirates, and crashed on a class-L planet. He spent three weeks fighting to survive in the hostile environment until his rescue. (PDN: "Survival Imperative")

In July, Sinclair took leave from the Pendragon and traveled to Earth to be there when his sons Jeff and Tyler were inducted into Starfleet Academy. (PDN: "Wanderers, Seekers, Warriors, Thinkers") Before he returned to the Pendragon, he helped Jordan Dennis solve the murder of their friend Jack McVey. (PDN: "Where the Silence Breaks")

2381
Early in the year, Sinclair and the Pendragon joined the USS Defiant on a mission to the Gamma Quadrant, and rescued General Martok and other survivors from Dominion Internment Camp 371. The return of the real Martok exposed the Changeling imposter and began the long process of restoring honor to the Klingon Empire. (PDN: "Destiny's Forge"; "Shadows of the Fire"; "Broken Sword")

While the Pendragon was docked at DS9 for repairs, Sinclair returned to Earth with Benjamin Sisko to testify before the Federation Council on the situation in the Demilitarized Zone and the recent developments with the Klingons. In the Council session, he stood up for Michael Eddington and the Maquis and asked that the Federation send more aid to the colonies, suggesting that one day soon they might become an independent nation. (PDN: "The Martyr's Diplomacy")

When the Council turned down the request, Sinclair surprised everyone by resigning his commission and disappearing. In reality, his resignation was a cover story devised by Admiral Coleman, who sent Sinclair and Justin Shive on a long-term mission into the Orion Syndicate to investigate the activities of Dr. Hugo Rossmer and their connection to the Tal Shiar activity in the DMZ, without attracting the attention of Admiral Nechayev. (PDN: "A Quiet Darkness")

Following leads acquired from Shayfaar, Sinclair discovered that former Admiral Erik Pressman was involved in the conspiracy, working with Rossmer and the Tal Shiar to perfect the interphasic cloak, work that had been interrupted five years earlier by Captain Steve Tecklenberg and the Eagle's Nest Squadron. Pressman tried to convince Sinclair of Tecklenberg's complicity in the operation, but Sinclair knew better, and pieced together that the Tal Shiar were planning to steal the new Genesis device under development at the Daystrom Institute by Dr. William Hoesch. Though they attempted to warn Hoesch, they were two late to prevent his abduction. The Tal Shiar planted evidence to frame Sinclair and Shive for the murder of two of the project staff, and Admiral Nechayev assigned Commander Tobias Moore to track them down. (PDN: "Cloak and Dagger")

Sinclair knew the only people he could turn to were the former Eagle's Nest officers, and they set out for Belle Terre to find John Seilback. (PDN: "Where Strength Begins") While on Belle Terre, Sinclair and Seilback entered The Captain's Table and recounted a tale from their days with Tecklenberg on the USS Scandalon. (PDN: "The Captain's Table: Bearers of the Light")

Sinclair, Shive and Seilback sought out Gehn, an old contact of the Eagles, who pointed them to an old Romulan outpost, where they found Dr. Hugo Rossmer. Sinclair and Seilback were captured by Colonel Vrian of the Tal Shiar, but Shive escaped to contact the other Eagles. (PDN: "Pilgrims on the Path of Shadows")

Taken to a cloaked Tal Shiar starbase on the outskirts of Cardassian space near the Badlands, Sinclair and Seilback saw the full extent of the conspiracy between the Tal Shiar, Obsidian Order and Section 31. They found Dr. Hoesch, as well as Captain Steve Tecklenberg, who had been held captive by the conspirators for five years. Sinclair was surprised to find Toby Moore among the conspirators, but understood when he relayed their location to the Pendragon and helped them escape from their cells. Moore remained behind to sabotage the Genesis device, while Sinclair and the others made for the shuttlebay. (PDN: "Salvation")

When it became clear that Moore had been discovered, Sinclair left the others and returned to confront Vrian. Seilback and Tecklenberg cut off Rossmer's escape even as the Pendragon arrived to engage the assembled Romulan-Cardassian fleet. She was badly outnumbered, though, Sinclair feared the worst until Shive arrived with two SEAL Teams, the Scandalon, commanded by Captain Tony Rupp, and a task force of other ships commanded by Eagle's Nest officers. With the distraction, Sinclair and Tecklenberg were able to free Moore, recover the Genesis device, and sabotage the station's stockpile of protomatter, destroying the base and much of the enemy armada, though Vrian escaped. (PDN: "Salvation Part II")

In the aftermath, Sinclair, Shive, Tecklenberg and the Eagles were debriefed by Admiral Coleman on Starbase 375. (PDN: "Memoriam")

2382
In May 2382, Sinclair and the Pendragon once again played host to Dr. Hoesch and the Genesis device, assisting in Phase II of the project. (PDN: "Diluvium")

A month later, Sinclair lost his first officer Russ Twining, chief engineer Josh Hofmann and security chief Benjamin Riniker when they and several other key personnel transferred to the USS Avalon. (PDN: "Avalon" and "Avalon, Part II")

In the wake of the Avalon departures, Sinclair made several changes to the Pendragon's command structure, which included promoting Mary Barranco to Commander and first officer, and making Jason Bartholomew helmsman. When Ben Bartholomew came to him after his wife's murder, Sinclair reactivated his commission and appointed him as operations officer. (PDN: "Tabula Rasa")

Some weeks later, Sinclair was a guest of honor at the commissioning of Liberty Station. (PDN: "Lighthouse in a Sea of Stars")

Sometime afterwards, Sinclair was drawn into a pocket universe created by Darrum, where he had married Mary Barranco after graduating from the Academy, Christopher Durham was alive, the Civil War had never happened, and he commanded the USS Ulysses. Sinclair's subconscious rebelled against the fantasy, and through great trauma, he escaped the Darrum's dream world. (PDN: "More To This Life")

Later in the year, Sinclair led an away team to Starbase 211 and discovered that Section 31 had been experimenting with Borg drones and nanoprobes recovered from the Battle of Sector 001. (PDN: "Distant Whispers")

2383
By early 2383, the Starfleet Command felt that the situation in the Demilitarized Zone had stabilized enough and reassigned the Pendragon. Sinclair initially fought this, feeling that there was still much more to do in the DMZ, but acquiesced to the order when Admiral Coleman informed him that humanitarian aid to the Maquis and Cardassians would continue. When he received his orders, Sinclair began to look forward to the Pendragon's next assignment, a three-month exploration survey along the galactic rim. (PDN: "Not Home Yet")

His enthusiasm dimmed when Coleman diverted the Pendragon to Delta Vega under orders from Starfleet Research and Development to recover the bodies of Gary Mitchell and Elizabeth Dehner. Sinclair soon found himself fighting for the lives of his crew when the same energy that mutated Mitchell possessed Ben Bartholomew. Sinclair was nearly forced to kill his best friend before a way was found to counter the effects of the galactic barrier. While the Pendragon traversed the energy barrier, Sinclair had a precognitive episode and glimpsed the lives of his family some thirty years in the future. (PDN: "Whispers As Loud As Thunder")

Later during the rim exploration mission, the Pendragon came across a mysterious, spider-like bioship. It evoked repressed memories in Sinclair from his time at the Enclave, and proved extremely difficult to defeat. (PDN: "Of Shadows and Starlight")

After returning from the rim, Sinclair accepted Jason Bartholomew's resignation, and was dealt an extremely heavy blow when Jason was killed mere days later. (PDN: "Charade")

2384
In the summer of 2384, Dr. Robert Blaisdell reappeared in Sinclair's life, revealing himself to be Flint the Immortal. Blaisdell/Flint recruited Sinclair and several other "knights" on a quest to find the Holy Grail, which Flint said was a vessel containing the ancient knowledge of the Preservers. Sinclair, Flint, Mark Montgomery and the others journeyed to Annwn, where they found a society of Arthurian-era Celts transplanted by the Preservers. Among the Celts, Sinclair discovered descendants of his ancient ancestors. (PDN: "The Once and Future King")

Early in the fall, Sinclair took leave from the Pendragon and went on walkabout. At a Daystrom Institute outpost, he found a modified Iconian gateway which transported him into the Dominion War timeline. While in that quantum reality, he discovered that while his counterpart had died nine years earlier, he and Jean had another child, who had been taken to the Enclave. Sinclair went to Titan and freed his counterpart's son, Benjamin Cody Sinclair, and returned with him to the Pendragon universe. (PDN: "Odyssey")

Late in the year, Sinclair confronted the conspirators who were poised to take control of the major Alpha Quadrant powers. The conspirators initiated Project Dragonslayer. As he was about to lead the Pendragon into battle against the Tal Shiar-led fleet, Sinclair was again drawn into Darrum's pocket universe. Darrum told Sinclair that if he continued on his present course, both he and his crew would die. Sinclair made a deal with Darrum: the power to save his crew, and in return, Sinclair would stay with Darrum. Darrum warned him that if he chose that road, the future he had seen for his sons would be different. Sinclair accepted and was returned to the Pendragon's bridge. He gave the order to engage the enemy armada, and though the Pendragon was nearly destroyed, the crew was spared. (PDN: "The Nautilus Coil"; "An Evening in Gethsemene"; "Dragonslayer"; "The Way to Camlann")

2385
With the Pendragon at Utopia Planitia for at least six months of extensive refit, Sinclair turned down command of the USS Hibernia and took shore leave, spending time in Colorado and Ireland, and also on Titan. (PDN: "Land of My Sojourn"; "Meditations on the Abyss")

When he returned to duty, Sinclair began teaching at Starfleet Academy. He also spent a lot of time with Mary Barranco, and their relationship continued to deepen. In March, Sinclair took Mary to Aldebaran Prime for a few days of R&R, to celebrate her birthday. Walking on the strand, he proposed to her, and she accepted. (PDN: "Faith My Eyes")

They were married on on Pacifica on 12 April 2385 (stardate 62278). The ceremony was performed by Captain Timothy Barranco aboard the sailing vessel Evenstar. Tyler Sinclair was the best man, and, Jordan Dennis, Ben Bartholomew, Steve Tecklenberg and Russ Twining were the groomsmen. The wedding reception was held at the Pax Maris resort, and afterwards Tecklenberg, Brady Thornton and other Captains in the party entered The Captain's Table to share a drink and tell embarrassing stories from the days when Sinclair served under them. (PDN: "The Significance of a Single Day"; "The Captain's Table: Cloud of Witnesses")

After his honeymoon, Sinclair assisted the government of a prospective Federation member world. (PDN: "Crosses & Crowns")

In July, Sinclair and Tecklenberg returned to Telamar III to settle unfinished business from twenty years before. (PDN: "Shadows, Part I and II")

Shortly after the Telamar affair, Sinclair resigned his commission. He met up with Vash once again, and she convinced him to join her work with a team of archaeologists on Mintaka III. Their research eventually led them to an ancient Tkon device, known as the Starkindler. (PDN: "Moments of Transition", "Another Time, Another Place", "Starkindler")

When he began showing signs of a mysterious genetic disorder, Sinclair realized that his time was short, and began wrapping up his affairs. This included an attempt at making peace with Toby Moore, which was only partially successful. (PDN: "Still Called Today")

Within several months time, Sinclair felt something calling to him. In the aftermath of the Battle of the Badlands, he used a mind-link to bring Ben Bartholomew out of his coma, bid farewell to his wife and sons, and left Federation space for parts unknown. (PDN: "The Hand of God")

Betazoid Lineage

 * see: Seventh House of Betazed

Human Lineage
On his father's side of the family, Tim Sinclair is descended from a long line of Starfleet officers and early United Earth heroes. His great-grandfather was Jeffrey David Sinclair, Commander of Deep Space Station B-5 in the 2250s, who later became a noted Federation Ambassador.

An earlier Sinclair ancestor was Timothy O'Neill, a member of the UEO Navy and hero of the Macronesian Conflict in the 2030s.

One of Sinclair's 20th century ancestors was science fiction author T.L. Morgan, a protege of Benny Russell.

Sinclair's ancestors fought in the Irish Revolution in 1916 and in the Irish Reunification in 2024.

Among Sinclair's ancestors during Earth's middle ages was an Irish monk named Alwyn, who resided in the monastery on Iona. In the 5th century A.D., some of Sinclair's ancestors were in a group of Celts transplanted by the Preservers to a world they would come to call Annwn.

Russ Twining
Though initially tentative around Russ Twining, Sinclair respected his first officer deeply, and through their service together, a strong friendship was born. One strong enough to weather the undercurrent of tension that returned between them when Twining learned that he was originally to be Captain of the Pendragon, but was passed over in favor of Sinclair. By the time of Twining's departure for the Avalon, however, the tension has smoothed out once again, and they are able to go their separate ways as comrades, fellow captains, and friends.

Mary Barranco
Mary Barranco was not Sinclair's choice for Operations Officer. Not because of any inability on her part, or any conflict between them. Only for one simple fact: he was in love with her. Ever since they had known each other at the Academy, a part of him always loved her. Though he thought that love dead by the time he was married (and remained faithful) to Jean, it sprung to life again the instant he saw Mary at DS9. For years after, though, he never told her, and their relationship remained professional and friendly toward one another, though Sinclair frequently found himself wrestling with his feelings for her. Feelings that were made much more complicated when his best friend, Ben Bartholomew, began to have the same feelings toward Mary, and especially when she reciprocated.

Only long after Mary and Ben realized that their relationship wouldn't work did Sinclair reveal his feelings to her. Fortunately for him, she felt the same, and they were married in 2385.

Ben Bartholomew
The relationship between Sinclair and Ben Bartholomew, went beyond friendship, beyond family. When they first met at Starfleet Academy, they had "difficulties." In short, they hated each other. But the Academy commandant saw fit to assign them as first squad mates, then roommates. Proximity bred familiarity, and from that came at first trust, and then genuine friendship. Seemingly overnight, Tim and Ben went from worst enemies to best friends. Sinclair had never had a family, and once their relationship had progressed, Ben became his family, and they even referred to each other as brothers, sometimes using the Betazoid term, ahikar ("precious brother-friend"). Ben's parents and brother also came to know and love Tim. Their bond only strengthened with time, through assignments both together and apart. Ben even became godfather to Tim's children, who called him "Uncle Benji".

However, when Sinclair learned that Bartholomew had joined the Maquis, he felt betrayed. But even that could not break the bond of love that he had for his brother, especially when Ben was presumed dead after the Klingon attack on Cervalis VI. Sinclair refused to believe it, knowing that Ben was still alive, and rescued him from the Tal Shiar nine years later. In the months that followed, Tim stood by Ben, helping him regain his stability. After Commander Twining's departure from the Pendragon, Ben even returned to Starfleet at Tim's request, taking the post of Chief Operations Officer.

Sinclair appreciated Ben's ability to balance his own point of view, and challenge his preconceptions. Even so, Ben's rebellious streak frequently clashed with Sinclair's calm, logical approach to most matters, and has led the two into numerous disagreements over regulations and moral choices. But the loyalty, respect, admiration, and brotherly love that the two men share knew no bounds, and always overcame any division between them.

Josh Hofmann
Josh Hofmann's happy-go-lucky, devil-may-care attitude served as perfect counterbalance for Sinclair's stoic, rational persona. Perhaps that was why they remained friends ever since their Academy days, and why, even after Ben Bartholomew's return, Sinclair confided in Hofmann more than anyone else. Following Josh's departure on the Avalon, Sinclair keenly felt that loss of support.

Mark Montgomery
As soon as the met at the Academy, Sinclair and Mark Montgomery were fast friends. It wasn't that they shared a common interest, or even compatible personalities, but something between them "clicked." The years after the Academy kept them apart, until their service together on the Christopher Pike. Throughout the Civil War, they relied on each other for stability and support while they saw the Federation crumbling around them. Montgomery was transferred off the Pike before the war's end, but afterwards, he was one of the first to come see Sinclair after Jean's death, and one of the few friends that Tim kept in contact with during his five-year retirement. Though not as close as Ben Bartholomew, Sinclair considers Mark one of his best friends, and one of his closest confidants.

Ancient history, languages, and the Preservers
From his upbringing on Titan, Sinclair grew to have an intense interest in archaeology, especially in regards to ancient and extinct species in the galaxy. He became a "Preserver chaser," and wrote several papers on the influence of the Preservers on galactic history, including:
 * Zeus & Rixx: The Common Myths of Earth and Betazed, which Sinclair wrote while attending Starfleet Academy and for which he received a special commendation from the Dean of Sciences.
 * Bloodstone's Forge: Tkon and Iconia, which was published in the Federation Journal of Ancient History in 2377. The work was commended by the Federation Archaeological Council.
 * From Arret to Mintaka: In the Path of the Vhorani, which was an examination of the spread of Vulcanoid races throughout the Orion arm of the Milky Way, and how the Romulan myth of the Vhorani was connected to Sargon and his ancient race.
 * When the Stars Changed: The Truth Behind Common Myth, which was Sinclair's magnum opus. Published in 2386, on his birthday, six months after his disappearance. The theories he proposed caused much controversy, but were generally lauded by Betazoid, Centaurian and Magna Roman scholars, and the Vulcan Science Academy even declared that Sinclair's research and conclusions were impeccably logical.

His research into those areas was aided by his eidetic memory and his natural skill at deciphering and learning different languages, both current and dead. By the time of his return to Starfleet in 2379, he could read or speak in 22 distinct languages.

Literature
Sinclair was an avid reader for as long as he could remember. His love of reading began in the Enclave, when Dr. Robert Blaisdell would give him books. It was one of the few activities he could indulge in outside of his training, and he devoured each one, from classic Terran works like Oliver Twist and the works of William Shakespeare, to T'Pau's Meditations on the Kir'shara and Shran's My Andoria.

His favorites were the ones that Blaisdell would sneak to him, because they weren't approved by the Enclave supervisors. These included The Once and Future King, The Magician's Nephew, Best Destiny, How the Irish Saved Civilization, the poetry of Tennyson, and even the Bible.

Irish heritage and music
During his teen years, when he was finally able to explore his own past, he became very interested in Earth history, especially that of Ireland, and also the United States of America. From his studies of Irish culture, and his father's Irish and Irish-American lineage, he fashioned his own form of cultural identity that had been denied to him at the Enclave.

Out of that grew his love of music, and he taught himself to play first the tin whistle, and then the bodhran, two instruments used in traditional Irish music, as well as the piano. After he met Steve Tecklenberg on Belle Terre, he came to recognize the shared lineage between traditional Irish tunes and the "cowboy music" of the American ancient west, and the two men would often play together, blending their musical styles. Years later, on the Pendragon, he would play with Russ Twining, Justin Shive and Ryan Dicker (who played the bagpipes).

Sinclair was fond of singing Irish and Scottish ballads, a habit he learned from his friend Will Kayden, who died at Setlik III. The Minstrel Boy was one of his favorites. The song Carrickfergus had special meaning for him, in light of his marriage and his wife's death.

Sports
When it came to organized sports, Sinclair was neither very gifted, nor very interested, but he nonetheless enjoyed playing Parrises squares, which he took up at the Academy with Justin Shive. He also briefly played on a water polo team with Ben Bartholomew and Mary Barranco. Mary also taught him basketball, and Mark Montgomery taught him to play football (soccer). But the game he truly loved was Teckball, a game invented by an ancestor of Steve Tecklenberg's in the 20th century that found a fanbase again on Belle Terre. Though he was never exceptionally proficient in any of these games, Sinclair enjoyed playing them with his friends, more than in competition.

In contrast to team sports, Sinclair was an avid outdoorsman. He enjoyed free climbing the Cliffs of Bole, deep sea diving on Pacifica, and sailing on Lake Armstrong, among many other activities.

Films and holoprograms
While exploring his father's ranch in Colorado as a teen, Sinclair discovered a library of OCDs from the pre-World War III era that contained a collection of 20th century and 21st century movies. He began watching them and became enamored with the ancient Terran films. Among his favorites were Casablanca, A Night at the Opera and The Court Jester.

It wasn't until the Academy that Sinclair first entered a holodeck (outside of the simulations at the Enclave). Eventually, he became quite fond of several holoprograms, including one based on the ancient Betazoid tales of Khrysaros and another one set in the Age of Sail on Earth. He would share those with Jordan Dennis and Ben Bartholomew, respectively. Later on, he would use the holodeck on the Pendragon to recreate his ranch in Colorado, and a "Hogan's Alley"-type shooting range, among other programs.

Pets
Sinclair owned many dogs during his life, beginning with "Digory," a male Golden Retriever. Sinclair acquired Digory as a pup, shortly after moving into his father's ranch in the early 2360s. After Sinclair's children were old enough to look after pets of their own, other dogs followed, and Digory became the "elder statesman" of the resulting "pack." He eventually sired at least one litter of his own, which produced "Samwise." Digory died in 2378, shortly before Sinclair's return to Starfleet. He was at least fifteen years old.

Other dogs that Sinclair owned included a Tervueren and a Siberian Husky, though these more likely belonged to his children, Jeff and Tyler.

After Sinclair returned from the "Dominion War timeline" with his son Cody, he gave the boy a Scottish Terrier, whom Cody named "Bruce." (PDN: "True North", "Wings as Eagles", "Midnight Clear", "Odyssey," et. al)

In addition, Sinclair owned a number of horses. Most were kept at the ranch in Colorado, though a few were housed on Belle Terre. Two of his horses were "Shadow" and "Remington." (PDN: "The Forgeman", "The Significance of a Single Day", "Wings as Eagles", et. al)

Chronology

 * 2341: Born in Christopher's Landing, Titan; orphaned and taken to Enclave J-12.
 * 2348: Escapes to Luna, encounters Mary Barranco; reclaimed by Enclave.
 * 2355: Leaves Enclave; visits Colorado and Betazed, rejected by the Seventh House; departs for deep space.
 * 2356: Encounters Vash and makes the "second biggest mistake of his life."
 * 2357: Meets Steve Tecklenberg at Belle Terre.
 * 2358: Travels on Beachmont; joins Academy, meets Ben Bartholomew, et. al.
 * 2359: Meets Bill Hoesch, and later, Jordan Dennis.
 * 2360: Advanced Tactical Training.
 * 2361: Cadre for Brad Powell and Toby Moore.
 * 2362: Graduates, marries Jean Brennan; assigned to USS Rutledge; Setlik III massacre, Durham dies.
 * 2363: Assigned to USS Cerberus; Jeff and Tyler born.
 * 2364: Cerberus destroyed; reassigned to Earth JAG; promoted to Lieutenant jg, assigned to Scandalon, joins Eagles.
 * 2365: Powell dies; visits Telamar III; assigned to USS Wayfarer.
 * 2366: Promoted to Lieutenant, assigned to Langley.
 * 2367: Wolf 359, teaches at Academy; Intelligence missions.
 * 2368: Promoted to Lt. Commander, assigned to Sutherland.
 * 2371: Promoted to Commander, assigned as XO on Chris Pike.
 * 2372: Timeline divergence; Civil War begins.
 * 2374: Civil War ends; Jean dies, resigns commission, returns to Colorado.
 * 2375: Dies at Second Battle of Chin'toka.
 * 2375 - 2378: Archaeological expeditions with Jeff and Tyler.
 * 2379: Commission reinstated, promoted to Captain, assumes command of Pendragon; rescues Bartholomew.
 * 2380: Encounters alternate selves on Manheim's Planet.
 * 2381: Gamma Quadrant expedition, rescues Martok; goes undercover, rescues Tecklenberg.
 * 2382: Avalon shakedown, crew reassigned, promotes Mary Barranco to XO; experiences pocket universe.
 * 2383: Mission to the rim, encounters galactic barrier.
 * 2384: Walkabout; alternate universe, finds Cody; gives up future to save crew, Pendragon nearly lost.
 * 2385: Marries Barranco on Pacifica; resigns commission, works with archaeologists; disappears into deep space.

Service jacket

 * [[Image:2366 - CDT4 (Command).PNG]] - Nebula Squadron, Starfleet Academy (2358-2362)
 * [[Image:2366 - ENS (Command).PNG]] - Flight controller, USS Rutledge (2362)
 * [[Image:2366 - ENS (Operations).PNG]] - Security officer, USS Cerberus (2363-2364), JAG office (2364)
 * [[Image:2366 - LTJG (Operations).PNG]] - Tactical officer, USS Scandalon (2364-2365), Asst. Security Chief, USS Wayfarer (2365-2366)
 * [[Image:2366 - LT (Operations).PNG]] - Security Chief, USS Langley (2366)
 * [[Image:2366 - LT (Command).PNG]] - Field instructor, Nebula Squadron, Starfleet Academy (2367-2368)
 * [[Image:2366 - LCDR (Command).PNG]] - Intelligence officer/Executive officer, USS Sutherland (2368-2371)
 * [[Image:2366 - CDR (Command).PNG]] - Executive officer - USS Christopher Pike (2371-2374)
 * [[Image:2373 - CAPT (Command).PNG]] - Commanding officer - USS Pendragon (2379-2385)

Starfleet

 * Starfleet Academy Cross - Awarded in 2359 for heroism in defending Federation citizens at great personal risk. Clusters added for meritorious conduct in 2360 and 2361.


 * [[Image:Starfleet_Academy_Top_15%25_of_Class.PNG]] - Awarded upon graduation among the top 15 percent at Starfleet Academy in 2362.


 * Presidential Unit Citation - Awarded to USS Rutledge crew in 2362 (stardate 39693.2) for heroism displayed while responding to the Cardassian attack on Setlik III.


 * [[Image:Bridge Officer Certification.PNG]] - Bridge Officer Certification, awarded in 2362.


 * [[Image:Cardassian_War_Service_Medal.PNG]] - Cardassian War Service Medal, awarded for service aboard the USS Rutledge during the Federation-Cardassian War.


 * [[Image:Starfleet_Citation_for_Conspicuous_Gallantry_Ribbon.PNG]] - Starfleet Citation for Conspicuous Gallantry, awarded in 2364 (stardate 41109.2) for valor displayed while saving the lives of twelve other officers aboard the USS Cerberus at great personal risk.


 * Commanding Officer's Citation - Awarded twice by Commander Stephen Tecklenberg for exceptional service aboard the USS Scandalon in 2364 and 2365.


 * Starfleet Distinguished Service Cross - Awarded in 2365 for actions taken to effect the escape of his away team after their capture by Cardassian forces.


 * [[Image:Extended_Service_Citation.PNG]] - Extended Service Citation, awarded in 2366.


 * [[Image:Battle_of_Wolf_359_Medal.PNG]] - Battle of Wolf 359 Medal, awarded in 2367 for service against the Borg in the Battle of Wolf 359.


 * [[Image:Command Officer Certification.PNG]] - Command Officer Certification, awarded in 2367.


 * [[Image:Grankite Order of Tactics.PNG]] - Grankite Order of Tactics, awarded for tactics devised on the Magna Roma mission in 2368.


 * Commanding Officer's Citation - Awarded three times by Captain Timothy Barranco for service aboard the USS Sutherland in 2368, 2369 and 2370.


 * [[Image:Career Service Citation.PNG]] - Career Service Citation, awarded in 2370.


 * Starfleet Intelligence Star - Awarded in 2371.


 * Commanding Officer's Citation - Awarded three times by Captain Brady Thornton for exceptional service aboard the USS Christopher Pike in 2371, 2372 and 2373.


 * Operation Return Medal - Awarded in 2374 for participation in Operation Return and the liberation of Earth.


 * [[Image:Legion of Merit Ribbon.PNG]] - Legion of Merit, awarded in 2382 for services rendered in defending and completing the Genesis project.


 * [[Image:Grankite Order of Tactics.PNG]] - Grankite Order of Tactics, class of excellence, awarded in 2385.


 * [[Image:Christopher Pike Medal of Valor.PNG]] - Christopher Pike Medal of Valor, awarded in 2385 for actions taken in defense of the Federation.

Civilian

 * Federation Archaeological Council Citation for Excellence - Awarded for Bloodstone's Forge in 2378.
 * Federation Archaeological Council Citation for Excellence - Awarded for When the Stars Changed in 2386.

Memorable quotes
"I have a life with my family. I can't give that up. Not for the galaxy, not for the Federation, not for you. You can find another poster boy!"

- Sinclair to Mark Coleman in "True North"

"Let's see where the wind takes us."

- Sinclair to Jason Bartholomew in "Tabula Rasa"

Background notes

 * Star Trek: Pendragon is a fan fiction series written (primarily) by T.L. Morgan. Images of actors are used in photomanipulations to simulate the "cast" of the series. In these photomanipulations, Timothy Sinclair is "played" by three different actors: Liam Aiken (as a child), Gregory Smith (as a teen and cadet), and Pierce Brosnan (as an adult).
 * Other actors considered for the role were Michael T. Weiss, Thomas Gibson, Ronald Coleman and Cary Grant. For the cadet Sinclair, Joshua Jackson and Brandon Routh were also considered.
 * Sinclair's "singing double" is Scottish singer/songwriter Jim Malcolm.