When Paul Reilly first stepped into the headquarters of Raymond James in St. Petersburg, Florida, back in 2009, the financial world was essentially on fire. Most people forget how grim it looked. It’s kinda wild to think about now, but he was taking over from Tom James, a man who had led the firm for four decades. Tom was more than a CEO; he was the firm's identity.
Paul Reilly didn't just walk into a job. He walked into a legacy.
Honestly, the transition was a masterclass in how to not mess up a good thing. Most incoming CEOs want to "disrupt" or "innovate" right out of the gate, which usually just means breaking stuff that worked. Reilly didn't do that. He spent a year as "CEO-designate," basically just listening and watching. He grew up as the third of eight children, so he’s always said that peacemaking and listening were his real superpowers. It sounds cheesy, but in the cutthroat world of wealth management, it was a tactical advantage.
The Era of the "Premier Alternative"
Under Paul Reilly, Raymond James stopped being just a "regional" player. You've probably heard people call it a "national powerhouse" now, and that’s largely because he leaned into a very specific niche. He positioned the firm as the "premier alternative" to the big Wall Street wirehouses.
Think about the context.
Advisors at places like Merrill Lynch or Morgan Stanley were feeling the squeeze of corporate bureaucracy. Reilly offered them a "client-first" culture that felt more like a boutique but had the tech budget of a giant. It worked. During his tenure, the firm’s stock price didn't just go up; it increased nearly 10-fold. By the time he started eyeing the exit in late 2024, client assets had ballooned to over $1.4 trillion.
Success leaves clues.
One of those clues was his refusal to take "unnecessary risks." He famously kept the company bank small—one branch, two ATMs—telling people he had no plans to double either. He wanted the bank to support the advisors, not the other way around. This conservative approach is why Raymond James sailed through the COVID-19 pandemic and the regional banking crisis of 2023 without breaking a sweat.
The $24 Million Goodbye and the New Guard
In January 2025, the headlines started buzzing about Reilly's compensation. For his final full fiscal year (2024), he was paid about $24 million. That’s a 17% jump from the year before. Some people on the internet—mostly in those advisor forums where everyone is grumpy—complained about "executive greed." But the board saw it differently. They credited him with driving record revenue and, more importantly, navigating the firm through two major hurricanes and a massive leadership hand-off.
Transitioning a $20 billion company isn't easy.
On February 20, 2025, Paul Reilly officially handed the keys to Paul Shoukry.
Shoukry is a different beast entirely—younger (42 at the time of the takeover), a former CFO, and a product of the firm’s "Assistant to the Chair" program. If Reilly was the bridge from the founder to the modern era, Shoukry is the one tasked with making sure the "Raymond James way" survives a digital-first world.
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What most people get wrong about the succession
People think Reilly is "gone." He isn't.
He moved into the Executive Chair role, a move identical to what Tom James did for him. It’s a "full-time" role. He’s there to mentor Shoukry and keep the culture from diluting. When you grow as fast as they have—adding thousands of advisors and hitting a stock price high of over $170 in late 2024—the culture usually gets watered down. Reilly's new job is basically being the guardian of the vibe.
A Legacy of "No"
Reilly often said that his and Tom James’ biggest contribution was saying "no." They said no to risky investments. They said no to private jets for executives. Fun fact: Raymond James remains one of the largest public companies without a corporate plane. Reilly even paid for his own parking space.
It's those small signals that kept the advisors from jumping ship.
Of course, it wasn't all sunshine. There was some friction. In 2024 and 2025, some folks grumbled about layoffs in the operations and RIA (Registered Investment Advisor) support segments. Critics argued the back-office service wasn't what it used to be. Some even called it "DEI-driven" or "corporate bloat." Whether those are fair critiques or just growing pains is something Shoukry has to deal with now.
Actionable Insights for Investors and Advisors
If you're looking at Raymond James today, here is the reality of the post-Reilly landscape:
- Watch the Culture: The "human-first" approach is the only thing keeping those 8,700+ advisors from leaving. If Shoukry gets too focused on the "CFO side" of the numbers, the "alternative to Wall Street" branding will fail.
- Focus on Recruiting: The firm is a recruiting machine. In fiscal 2024, they brought in advisors representing $335 million in revenue. In 2025, that jumped to over $400 million. As long as that number stays high, the stock (RJF) stays healthy.
- The "Executive Chair" Factor: Don't ignore Reilly's presence. Having a former CEO as Executive Chair can be a double-edged sword, but historically at Raymond James, it has provided the stability that prevents the "new CEO jitters" seen at other firms.
Paul Reilly basically took a Florida-based brokerage and turned it into a global name without losing its soul. That’s a rare feat in finance. He didn't try to be the smartest guy in the room; he just tried to be the best listener.
Now, we see if the "peacemaker" style of leadership can survive the next decade.
Keep an eye on the upcoming quarterly filings. You'll want to see if the Private Client Group (PCG) under Tash Elwyn continues to grow at its current 8% clip. That’s the real engine of the company. If that stalls, the Reilly era will look like a peak that was impossible to maintain. If it keeps going, he’ll be remembered as the guy who built the most solid foundation in the business.
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Check the latest proxy statements to see how the new leadership's compensation aligns with advisor retention—that's the "canary in the coal mine" for this firm.