Josh Brown recommends sticking with these three winning stocks

Ritholtz Wealth Management’s top executive, Josh Brown, is recommending investors stick with three outperformers through the end of this year (2026).

His top picks – Interactive Brokers, Caterpillar, and Delta Air Lines – have notably outperformed the broader market in recent months, which Brown believes justifies owning these names for the long term.  

According to him, positions that keep working need no new reason to stay in your portfolio.  

Interactive Brokers (IBKR)

IBKR shares have been on Brown’s list of “Best Stocks in the Market” ever since they broke out of a cup-and-handle pattern in mid-2025.

In the trailing 12 months, the global electronic brokerage firm has rallied a remarkable 80%.

Brown attributed part of this explosive move to a float that’s small relative to founder Thomas Peterffy’s stake – limiting supply as demand persists.

Crucially, Interactive Brokers’ Q1 results back up the chart: client accounts grew 31% year over year to 4.75 million, client equity rose 38%, and margin loans climbed by some 40% to US$90 billion (approx. $125.5 billion).

In the first quarter, the company’s commissions hit a record US$613 million (approx. $854.5 million) – with stock, futures, and options volume all posting double-digit annual gains.

A 0.36% dividend yield makes IBKR even more attractive to own in 2026.

Caterpillar Inc (CAT)

Caterpillar stock joined Brown’s list in April primarily because of its Power and Energy segment’s exposure to the AI infrastructure buildout – a thesis that has since strengthened.

In Q1, the company’s power generation sales grew a whopping 48% year-over-year – pushing the order backlog up 79% to record levels.

This even prompted management to raise its 2026 revenue guidance and more than triple its long-term power generation target through the end of this decade.

Despite a 270 bps tariff hit, CAT’s adjusted earnings per share (EPS) came in up 30% in the latest reported quarter.

Note that a gas engine running continuously for data centers generates about 40x the lifetime services revenue of a standby diesel unit.

Caterpillar remains attractive also because its board lifted the quarterly dividend recently to $1.63, extending a 32-year streak.

At writing, the firm’s share price is up nearly 45% versus early April.

Delta Air Lines (DAL)

Josh Brown first shared his constructive view on Delta Air Lines stock in December 2025, and it’s gained more than 20% since then.

The rebound has been led by premium and corporate demand: premium revenue grew 14% in Q1, loyalty sales came in up 13%, while corporate bookings hit a quarterly record.

The main cabin posted positive unit revenue growth, its first since late 2024, with domestic revenue and international revenue gaining 6% and 5%, respectively.  

A record US$14.2 billion (approx. $19.8 billion) in Q1 sales saw free cash flow hit US$1.2 billion (approx. $1.7 billion), with the outlook for the current quarter pointing to low-teens revenue growth.

Much like the other names on his list, DAL shares also currently pay a dividend yield of 1%.