Cap'n Hawkes

Sutter Hawkes was First Mate on a merchant ship.  He is a renowned pilot, shrewd negotiator, and not so bad with the ladies.  His first love is deep water sailing to chase monsters.  As a youth, Hawkes was educated and studied biology, particularly of the sea.  His hypotheses were largely discredited, provoking him out into the depths for proof.
 During a recent war, his ship was commandeered and he served as a conscripted privateer.  Their government appointed commander, however, went mad and murdered the ships captain.
 Hawkes led the crew in restoring order and assumed command, bringing the commander back in chains for court martial.   But the stories of other crewmen and Marines varied and the commander's counter-accusation of mutiny stuck. Hawkes slipped away due to the benevolence of fellow pirates during transport to a secret island prison.
 Hawkes, a villain to some and a symbol against tyranny for others, has done very little to earn his reputation.  None the less, he will do his best to live up to both until his name is cleared and the crooked judges that burned him are exposed. Somehow, his dues for the Merchants guild is always paid on time.

Cap’n Hawkes
Half elf merchant
Chaotic Good
F (battle master) 5 / Bd (Lore College) 7

St 10.   save+4
Dx 20.  Piloting +13
Co 12   save +5
In 10.
W.12.   piloting +9
Ch 16

Hp. 86
AC 18 Studded leather +1, dex

+2 Sun Blade +11 1d8+7 radiant (Finesse)
+2 dagger +11 1d4+7 (3d6 venom 1/day)
+2 rapier +11 1d8+7
Dragon pistol 1d4+5
Brace of pistols +9 1d6+5?

40 bullet loads
40 pellet loads
80 powder loads

Two-weapon fighting

Proficiency +4 (Jack of all trades = prof ÷2)
Strength and Constitution saves
History, nature, arcana +4
Fiddle +7
Water vehicles(x2) +8/+11
perception +5
insight(x2) +9
persuasion/deception +7
navigators tools +4
Athletics +4
survival +5
Stealth +7 Advantage

Languages: Common, Elvish, Draconic, Celestial

Superiority dice (d8): 4. (short rest)
Maneuvers: Commanders strike, maneuvering attack, pushing attack Dc17

Bardic inspiration: d8 3/short rest
    You can inspire others through stirring words or music. To do so, you use a bonus action on your turn to choose one creature other than yourself within 60 feet of you who can hear you. That creature gains one Bardic Inspiration die, a d8. Once within the next 10 minutes, the creature can roll the die and add the number rolled to one ability check, attack roll, or saving throw it makes. The creature can wait until after it rolls the d20 before deciding to use the Bardic Inspiration die, but must decide before the DM says whether the roll succeeds or fails. Once the Bardic Inspiration die is rolled, it is lost. A creature can have only one Bardic Inspiration die at a time.

Cutting Words
  Also at 3rd level, you learn how to use your wit to distract, confuse, and otherwise sap the confidence and competence of others. When a creature that you can see within 60 feet of you makes an attack roll, an ability check, or a damage roll, you can use your reaction to expend one of your uses of Bardic Inspiration, rolling a Bardic Inspiration die and subtracting the number rolled from the creature’s roll. You can choose to use this feature after the creature makes its roll, but before the DM determines whether the attack roll or ability

Additional magic secrets: Hunters Mark and Fireball.

Song of rest 1d6

CountercharmAt 6th level, you gain the ability to use musical notes or words of power to disrupt mind-influencing effects. As an action, you can start a performance that lasts until the end of your next turn. During that time, you and any friendly creatures within 30 feet of you have advantage on saving throws against being frightened or charmed.A creature must be able to hear you to gain this benefit. The performance ends early if you are incapacitated or silenced or if you voluntarily end it (no action required).

Spells: 1:4. 2:3. 3:3 4:1
Cantrip: Vicious Mockery 3d4, Message, minor illusion
1: charm person, bane, healing word, detect magic, identify, hunters mark
2: suggestion, shatter, invisibility,
3: fear, fireball
4: freedom of movement
Spell Save 15

Equipment:
Diplomat's Pack (39 gp). Includes a chest, 2 cases for maps and scrolls, a set of fine clothes, a bottle of ink, an ink pen, a lamp, 2 flasks of oil, 5 sheets of paper, a vial of perfume, sealing wax, and soap.
Travel clothes
Backpack
Bedroll
Block and tackle
Caltrops
Grappling hook
Hemp rope
Scale
Signet ring
Signal whistle
Tinder box
Water skin
Whetstone
3 sacks
4 rations
Pouch
Mirror
Fiddle
Disguise kit
Forgery kit

Unwavering Diplomacy Ring (blue stone). (Requires attunement)
Grants immunity to the Stunned condition.
Once per day, you may grant yourself advantage on any Persuassion skill check.

Studded Leather Armor of the Lion +1
 Advantage Con save 1/day

Sunblade +2 (attuned) 2d8 vs undead, sheds light

IOun stone awareness (requires attunement)

Ring of water walking

Ring of spell storing (attuned)

Boots of elven kind (no attunement needed)

Instrument of the Bards, Canaith Mandolin (attuned)
 You can play the instrument while casting a spell that causes any of its targets to be charmed on a failed saving throw, thereby imposing disadvantage on the save. This effect applies only if the spell has a somatic or a material component.
 Spells: fly, invisibility, levitate, protection from evil and good, cure wounds (3rd level), dispel magic, and protection from energy (lightning only).

Treasure on person
Pp 873
Gp 1063
Sp 6
Cp 12

2 pale green zircon worth 50 gp
2 pearl (100gp)
2 gems 1000gp
1 ivory figurine 250gp

Treasure in Amonah Anah
Pp 3000
Gp 7000

Ph

Captain Hawkes

AC AC 18
Hp 86/86. (96/96 For 24 hours)
HD 5d10
7d8
Spell save 15
Passive perception 15
Passive insight 17

Second Wind d10+5 (short rest)

Action surge (short rest)

Superiority dice (d8): 4. (short rest)
Maneuvers: Commanders strike, maneuvering attack, pushing attack Dc17

Bardic inspiration: d8 3/short rest
Adv. Con save 1
Venom dagger (+3d6) 1

Spells:
1:4
2:3
3:3
4:1
Mandolin spells 1/day
fly
invisibility
levitate
protection from evil and good
cure wounds (3rd level)
dispel magic
protection from energy (lightning only)

Stored spells in ring:
Find traps
Revivify

Temporary Buffs
Immune to poison, immune to “frightened”, and advantage wisdom saves

You have a lot of buff/debuff/crowd control, well done. Plus he is a solid melee fighter to boot

GM gonna have to up his game now....

Next levels

Bard 8
Lucky Feat
+1 4th level spell per day
+6 hp

Fighter 6
Feat
+8hp