James (Jim) Castas Philippou, age 42, of Tallahassee, FL, left us March 17, 2020 to be reconnected with his beloved dog, Miller, for an eternity of playing with tennis balls and shared steak dinners. Jim is predeceased by his dog, Miller and survived by his parents, Phil and Karla Philippou of Clearwater, FL; brother John Philippou of Las Vegas, NV; sister Laura Ayre, and her children Eli and Emma, of Holiday, FL; his fiancée Hillary Haythorn and her daughter Kaitlyn Okleja of Tallahassee, FL; and myriad other friends and family whose lives are forever better because of Jim’s impact.
To best understand and remember Jim, it is most important to start with his journey and to end with a reflection of the unprecedented impact, legacy, and standard for living that he leaves us to remember and pursue.
Jim was born February 1, 1978, to Phil and Karla in Manhattan and was raised in Clearwater, FL. Jim was the first of three siblings, followed by his brother, John, and sister, Laura. If you were to ask Jim, he was clearly the favorite sibling. And the smartest. And the hardest working. And the best-looking. Yet, regardless of his self-proclaimed superlatives (which he would tell you are merited and earned), what is most important to know is that he was loved and appreciated as a son and brother – and accordingly – his family’s actions encouraged him to love and appreciate those who he met in his next stage in life.
Jim was a class favorite upon graduating from Countryside High School. After graduation, he attended the University of Central Florida. Jim made many lifelong friends while at UCF supporting his Knights and becoming a local celebrity by having his picture inside the Student Union on campus. Many of these friends became part of Jim’s “Camping Crew” with whom he would camp every year on MLK Day weekend. As many know, after a weekend in the woods, bearded Jim would spend days bragging on how much fun it was to shoot guns, ride four-wheelers, and catch-up with his buddies. Yet, what is most important to know is that he was loved and appreciated as a friend – his Camping Crew’s actions encouraged him to continue to love and appreciate those who he met in his next stage in life.
After spending time in Orlando, FL, Jim moved to Tallahassee, FL – Jim’s time in Tallahassee had two stages, his car days and his bank days, both referring to his chosen career. Jim’s move to Tallahassee was to continue his pursuit of a finance career in the auto industry with Hyundai and, subsequently, at Champion Chevrolet. This move to Tallahassee is where Jim eventually found his Miller Dog – for those that don’t know, Miller came with the house that Jim purchased as the owners could not take him. Miller became Jim’s inseparable companion. Also, in Tallahassee, Jim met his “Car Guys and Bar Guys” – a group of locals that Jim met through his experiences in the auto industry that went on to become his next group of friends and would often connect after work to unwind after stressful days. To all he met it was clear – Jim was talented beyond words and compassionate beyond reason. Through his actions, he forged his new friendships in his new home. Yet, what is most important to know is that he was loved and appreciated as a colleague, mentor, confidante, and friend – and accordingly - his Car Guys’ and Bar Guys’ actions encouraged him to continue to love and appreciate those who he met in his next stage in life.
Jim’s second stage in Tallahassee saw him move on from the auto sales industry and to working at Capital City Bank – leading their auto finance sales. To put it bluntly, Jim successfully transformed the bank’s auto finance portfolio by taking his firsthand knowledge from the other side of the business and applying it to his new role. And what subsequently came at this same time was a parallel transformation in Jim – an evolution that saw him pursue his new career, re-ignite his passion for flying, set his sights on traveling, and finding love. Over this time, Jim chased everything: new accomplishments at work, more hours in the cockpit, more experiences domestically and abroad, and more time with the women who he had asked to be his future wife and daughter, Hillary Haythorn and Kaitlyn Okleja, respectively. Jim’s new colleagues, Hillary, and Kaitlyn were significant to Jim’s second stage in Tallahassee: they helped Jim to find new passions and a family to love and call his own. During this time, Jim achieved all that was set in front of him and found his true love. What is most important to know is that he was loved and appreciated as a professional, pilot, traveler, and most importantly, future husband and father – and accordingly - his new colleagues’, Hillary’s, and Kaitlyn’s actions encouraged him to continue to love and appreciate those who he was set to meet in his next stage in life.
For those who knew Jim something notable came from the accumulation of love and appreciation – we saw a man who reached the pinnacle of happiness. And that happiness is a great place to begin reflecting on Jim’s impact, legacy, and standard for living that we are all so blessed to have witnessed and will have the opportunity to carry forward in our own lives.
Jim was talented – talented enough to have successfully played the role of son, brother, uncle, friend, colleague, mentor, confidante, professional, pilot, traveler, and future husband and father. In fact, his talents outweighed those of the 53 men called the 2019 Tampa Bay Buccaneers, his beloved football team. It is important to relate Jim’s life to his love of football, because Jim treated his family, friends, dog, colleagues, and loved ones like he was playing in a personal Super Bowl every day – and he always wanted to win your MVP award. Unquestionably, Jim found a way to be everyone’s personal MVP through his love and appreciation for those close to him that was nurtured from an early age by his family.
Jim was committed – he fully committed himself to his everyone in his life, and always gave them 100%. He always spoke of being “committed like the pig” – an anecdote relating a pig’s sacrifice to breakfast. The anecdote goes that the pig sacrificed his life to become bacon or sausage, whereas the chicken only needed to sacrifice its eggs and was not “fully committed”. Jim always sacrificed himself to establish levels of camaraderie, trust, and love his relationships that cannot be matched. He ensured that anyone within his circle, new or old, felt his commitment. If you recollect for a moment, it’s easy to recall the first time you felt Jim’s commitment.
Jim was stubborn – stubborn to uphold his end of the love, appreciation, and commitment, and expected everyone else to step up, as well. And to be clear, we are not ignoring that Jim was also stubborn in an obstinate and argumentative way, too (you are certainly grinning because you remember that one time…); however, we will focus on the former, not the latter. His stubbornness was admirable – he was determined to ensure he held himself and those around him to the highest expectations.
Jim was happy – in fact, his happiness was because of us, all of us. Jim was energized by the people around him. Take a moment to realize, you helped power the machine and kept him going. Jim was never so happy as when his people were surrounding him. Further, in recent years, Jim found a new level of happy, only made possible by his future wife and daughter-to-be, Hillary and Kaitlyn. We all knew happy Jim, but they unlocked something new in Jim – a Jim who wanted to be a better version of great. And he was happy to do that.
All told this was James, Jimmy, Jim, Jimbo, Poo, or any other name you knew him by – our MVP, son, brother, uncle, friend, colleague, mentor, confidante, professional, pilot, traveler, and future husband and father. But stop for a moment, and reflect on how you can live like Jim every day, because it is what he would have wanted you to do:
- Be talented and accept the role that those around you need; learn to adapt to people. That’s what Jim did.
- Be committed and give your 100% 100% of the time – you owe it yourself and your circle. That’s what Jim did.
- Be stubborn. Don’t bend for convenience and don’t change your core values. That’s what Jim did.
- Be happy and grateful for the people you have around you. Life is precious, too short, and never guaranteed – so leave it all on the field. That’s what Jim did.
Finally, relish in Jim’s last gift to all of us, one so befitting, it’s impossible to ignore. As you are all aware, Jim was invigorated by being surrounded by those he cared about and always enjoyed when those people celebrated him. To allow that tradition to last forever, Jim stole St. Patrick’s Day for himself and left it to us as a final gift. Remember each year, on March 17, you will no longer be able to celebrate St. Patrick – you will be celebrating our MVP, son, brother, uncle, friend, colleague, mentor, confidante, professional, pilot, traveler, and future husband and father – James Castas Philippou.
Jim, thank you for being you. Thank you for your love. Thank you for your compassion. Thank you for being what we needed, when we needed it. Thank you for never giving up on us. We love you and miss you already – give Miller dog a hug.
~Composed by: Ray Vincent
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