The Ascent of Power: Drew Streets

[KenH]

By JoJo Franks

A dark day! The Featherheads’ beloved Farmers Field is no more!

Perhaps many will look back at the night of Friday, January 18th 2030 and remember the moment that Drew Streets, already primary shareholder in the Florida Featherheads franchise, took the final step towards unprecedented control of the franchise. On that night, after months – perhaps even years– of constant power plays and backroom deals to established himself as the singular majority shareholder for the Florida baseball club, a surprise press release was announced near the end of business Friday…

“In the pursuit of leading the Featherheads franchise to the greatness that Mr. Streets and the board wish to see, Mr. Streets has initiated a purchase of 5.25% Featherheads ownership from each Mr Drysdale, Mr. Frich-Leichtman, and Mrs. Yamamoto. With this purchase, Mr. Streets – entrepreneur, venture capitalist, and philanthropist – has taken a 51% stake of the franchise.

It is with this transaction in mind that the Florida Featherheads organization is excited to announce some evolutions of our brand…

As of now, Farmers Field is now renamed to “Streets Casino & Holdings Park at Jacksonville”
All prior “traditions” of the Featherheads that, while initially done in good faith, are to be suspended. This includes the “wigwam” in the leftfield corridor and the selling of “authentic” Featherheads-branded tribal headdresses at the team store.
Starting on opening day, a new “Streets Experience” will open. Located on the Mezzanine along the third base side, guests will be able to get the true “Las Vegas Experience” right from downtown Jacksonville – win big in the Danny Burton slot machines or play blackjack with your friends. Explore the natural wonder of Mr. Streets’ 700-acre ranch among the foothills of Denali or his majestic 10-bedroom villa overlooking the ancient city of Dubrovnik, Croatia in a one-of-a-kind virtual reality booth. Further, see if you have what it takes to run a casino yourself with an interactive game that tests your business acumen and mettle!

While we expect some of these changes to be challenging to some, Mr. Streets and the rest of the board wish to foster a sense of inclusivity and to lessen unwelcome distractions at Featherheads home games.

Throughout the year, expect more announcements as we unveil the future of our club.

Are you ready… for a new generation of Florida baseball?”

In what can only be considered an extreme departure from the established order of the otherwise conservative business decisions of 3/4ths of the principle owners of the Florida Featherheads, it may seem as though the reins may be finally removed from Streets’ flamboyant business sense… and his big city sensibilities.

Stories have always circled regarding the negotiations of the 4 owners of the club, however there had not been much movement on this front until very recently. Even as early as last week, the premise of a Streets takeover remained laughable on its face. Especially as it pertained to Schubert Drysdale and Hans Frich-Leichtman, the board had veto power which, according to secondhand reports, had been implemented in the past. The three “silent owners” were, by all intents and purposes, secure and happy to collect dividends commensurate with their minority stakes in the team. So, what changed? At some point, between the new year and now, a power shift within the Florida higher-ups had completely upended years checks and balances.

What these changes entailed and how they came to be, however, will require a deeper look into the last two decades of the Featherheads franchise. In part two of our continuing expose of the power shift, we will discuss one possible theory as to what made this transition of power happen… and what this shift may portend for the future of the club.

[Ghosts]

Not sure how I missed this, but kudos to Mr. Streets on his strategic successes. I'm interested in seeing how he evolves Florida baseball.

[Sandgnats]

Streets is my favorite owner in PEBA. Fascinating story-line... How woke will he go?

[Ghosts]

Streets is my favorite owner in PEBA. Fascinating story-line... How woke will he go?

I've started to write David Novak as almost the opposite. That way when he passes away in the game I won't have to pretend to mourn his economizing.

[Sandgnats]

Streets is my favorite owner in PEBA. Fascinating story-line... How woke will he go?

I've started to write David Novak as almost the opposite. That way when he passes away in the game I won't have to pretend to mourn his economizing.

I feel the same way about Mr. Dole, my owner... I feel the pain in the wallet too Dan.

[Borealis]

With some of the crazy contracts that are out there, it's a good thing we have some stingy owners - otherwise it would be an insane landscape...

[Ghosts]

With some of the crazy contracts that are out there, it's a good thing we have some stingy owners - otherwise it would be an insane landscape...

Leave Bothwell out of this. I learned my lesson

[Borealis]

With some of the crazy contracts that are out there, it's a good thing we have some stingy owners - otherwise it would be an insane landscape...

Leave Bothwell out of this. I learned my lesson

[KenH]

PART 2...

While full reports have not been given, many believe that it has to do with questions swirling Streets’ belief in first time GMs – first with a green Kevin Lewis in 2009, then with Ken Hannahs in 2023.

In what can only be described as “Machiavellian” in design, reports are that Streets made power plays early and often to get “his guy” into the top spot throughout the last twenty years of Featherheads baseball. While this may read as a bit of a conspiracy theory, we will endeavor to lay out several factors that we can objectively point to as, if not definitive proof, at least convincing of Streets’ grand design taking shape.

In 2008, Drew Streets was already a famous entrepreneur – owning a cruise line and casinos – decided to branch out and buy a baseball team. The problem for Streets was that ownership of a team wasn’t as simple as simply “buying a team.” Back in 2008, PEBA was still nascent. After the fall of the MLB, many franchises had been doled out simply to the highest bidder. With the league forming, but many still believing that there was money to be made, the ability to simply buy out a team without paying an exorbitant markup, was simply not possible. However, one option presented itself: The Florida Featherheads. A so far unsuccessful team, the ownership was not as settled on the success of the PEBA experiment or, more explicitly, the success of the club that made their home among the muggy confines of Farmer Field.

In stepped Mr. Streets.

While we cannot read Streets’ mind back in 2008, we can flash back to his first ad where he introduced himself as the plurality owner of the Featherheads. In what is now considered a bit of iconic PEBA advertising, the image of Drew saying that he was “expecting a new brand of Featherheads baseball” from his cabana chair now is seen as a clue towards his larger goals, 20 years before its activation. While this, at first glance, could be shrugged off as conjecture or logical fallacy, let us remember the final line of that ad as the screen went to black… “Are you ready… for Florida Featherheads baseball?” The first part of this line is exactly the same with the final line of the aforementioned press release… save the part about the team name… and the city. We’ll come back to this point later – but for now, let’s focus on Streets’ rise in power and predominance within PEBA and how he secured himself as one of, if not the most, influential owner in the league.

When Streets purchased his stake in the team, he had a condition. One up until now wasn’t entirely known and is, even to this day, hazy at best. He wanted his guy in the driver’s seat. He wanted Kevin Lewis.

On December 1st, 2008, Kevin Lewis sat down with Jacksonville Sentinel staff writer Serenity Summers to conduct an interview about how he came into the position. For many budding F-Heads, the interview read like a terrifying glimpse into a future that would be full of mediocrity and sadness. Lewis, who is now credited as the builder of one of the most consistently successful franchises in PEBA, came off as a Drew Streets yes man. And, in a way, he was. Streets tasked him with reinventing the image of Featherheads into a winning organization – and he did. In Kevin Lewis’ third season, the Featherheads won their first Rodriguez Cup. The exploits of Kevin Lewis and Drew Streets do not need rehashing here – this only to show the alacrity with which Streets and Lewis worked to revamp a team into winners quickly.

With their team growing by leaps and bounds and fresh off their first Rodriguez Cup victory, Streets bought out another stakeholder in the team, a Dr. Millie Hayes, furthering a slowly building takeover of the Florida ballclub.

For the rest of Lewis’ time at the helm, the club was stable. Ironically, this probably had more to do with just how successful Streets and Lewis were at creating winners. “Rats don’t jump ship when the gettin’s good,” quipped one source. “The silent owners had no reason to split – even when presented with a cruise ship full of cash.”

And so, the reign of Lewis was otherwise marked with consistency… perhaps even more than Streets would have wanted. What Streets needed was something else. Something weird to happen. That something weird did happen but perhaps not the way that anyone could have expected.

In the next and final installment, we will go deeper into what became, in a sense, a hostile takeover. This was in no small part to the emergence of Ken Hannahs after the departure of Lewis.

[KenH]

While power dynamics were already in flux when Ken Hannahs came on board, Hannahs’ and Streets’ relationship became a dynamic that boosted the first-time GM’s stature in the eyes of the Featherheads executives, giving him enough slack and seemingly ever-increasing budgets.

“It’s no surprise that Hannahs owes most of his rise to his ability to get in the good graces of Drew [Streets],” grumbled one staffer who spoke under anonymity. “Those two have always been joined at the hip – I bet they’re really enjoying tearing down the tent poles that was this franchise.” The staffer paused for a moment before adding “Well, at least they throw good parties.”

Seemingly a nobody, Streets had a known affinity to the young GM-to-be. “I’m not one to gossip, but I heard that Hannahs got the job primarily because he had some dirt on Streets – but you didn’t hear that from me,” dished one employee. “All I’m saying is, isn’t it strange that Lewis leaves, Hannahs comes on, and all of a sudden Hannahs goes on a spending spree… decidedly not Lewis-like.”

It’s not to say that things haven’t gone OK for the Featherheads. Indeed, the Featherheads won their first 6 division titles while being helmed by Hannahs and, of course, won the Rodriguez Cup in 2025. However, it was evident that the team has been much more frustrating… big contracts were almost immediately doled out to Dave Crocker, Kensaku Gato, and Jose Diaz. Right fielder Tony Velazquez was traded away for basically nothing. Lewis’ GM-ing was a constant… Hannahs’ started markedly differently.

The series of events that led to a redistribution of resources and a less profitable club has still seen success, but it has spooked investors. The one-time insanely profitable franchise has found itself income-impotent in the past few years, managing paltry returns on investment, due in large part to expensive ageing players and a ballooning budget partly subsidized by Streets’ seemingly bottomless reservoirs of liquidity.

Investors are, as they say, “spooked.”

Spooked enough to sell about 5% of their stake in the franchise. Spooked enough to allow the casino and cruise magnate a controlling stake in the franchise.

In a sense, 2030 is a culmination of events – an apocalypse that had been foretold in the strings of franchise fate. The Featherheads seem to have run out of luck. The Thoroughbreds hold a resounding 11.5 game lead in the Dixie division going into the last two months of ball. The Featherheads are saddled with immovable contracts by way of Danny Burke (a direct link to the Kensaku Gato contract Hannahs signed early on in his tenure) and not enough space to negotiate an ageing core of players. Streets and Hannahs are like the pilots of the Titanic, watching helplessly as the once unsinkable ship collides with the cold, uncompromising glacier.

There is a pall to the crowd at the games. They are watching the end of the season approaching with the same apprehension as the players. They all can see what’s coming. It started after the all-star break when the Featherheads traded Kang to the defending champs for a younger starter Jorge Alvarez and 20-year-old fireballer Erskine Hill. Rumblings are that there may be even more to follow.

All of this is to say that, with the Streets coup, the almost definite break in continuous division titles, and the selling off key assets, the Featherheads are doing something that many fans in Jacksonville haven’t seen in over two decades.

This restlessness among player and manager and fan has also manifested in other ways both small and large. Despite a similar team, Florida’s seen tower ticket sales despite lower prices. Despite leaders and veterans, signs of discouragement and fracture in a once harmonious clubhouse. Despite over two decades of tradition, fans the drumbeat of progress rages outside the stadium. More and more fans are joining the chants outside the stadium during home games, demanding the team find a new moniker.

In a year where so much is unknown about the future of the franchise, why not throw one more unknown onto the fire?