'Winners win' — Josh Brown on three winning Best Stocks to keep riding

The article is broadly constructive on Interactive Brokers, Caterpillar, and Delta, highlighting strong fundamentals, upward price trends, and supportive technical setups. IBKR reported Q1 2026 client accounts up 31% to 4.75 million, CAT's power generation sales rose 48% with backlog up 79% and the dividend increased 8% to $1.63, and DAL posted record Q1 revenue of $14.2B with a 15% dividend hike. Each stock is described as pressing higher or consolidating near key breakout levels, with stops provided for traders and investors.

Analysis

The common factor across these names is not just momentum, but self-reinforcing operating leverage tied to scarce capacity. IBKR benefits when volatility and turnover stay elevated; CAT benefits when AI infrastructure spend stays concentrated in power generation and backup systems; DAL benefits when premium travel demand stays resilient enough to offset fuel noise. That makes this more than a simple “winners win” tape — each stock is monetizing a different bottleneck, and bottlenecks tend to compound before they mean-revert.

The second-order implication is that these businesses are becoming less cyclical than their labels imply. IBKR’s rising account and margin balances should keep monetizing even if rates drift lower, because activity and balances now matter more than pure rate carry. CAT’s data-center exposure creates a multi-year services annuity that should soften headline industrial cyclicality, while DAL’s premium mix and loyalty revenue make it increasingly a consumer discretionary proxy with a quasi-subscription layer.

The contrarian risk is crowdedness: all three have enough visible upside that they can become “good enough” owned names, vulnerable to air pockets on any disappointment rather than obvious fundamental breakdowns. The near-term catalyst set is simple — next earnings and guidance updates — but the real risk horizon is 3-6 months, where expectations can outrun the pace of incremental beats. If markets rotate away from quality growth or if macro volatility compresses trading activity, delays AI capex, or weakens premium travel, these names can correct faster than the fundamentals deteriorate.

My base case is that the setup still favors staying long, but selectively adding only on technical pullbacks rather than breakout-chasing. The best asymmetry is in names with rising estimates and visible support levels, because a failed breakout would likely offer a cleaner re-entry than a momentum extension above round-number resistance.

Key Decisions for Investors

• Stay long IBKR into the $100 level, but add only on a pullback toward the low-$90s; risk/reward remains favorable as long as the stock holds above the prior consolidation, with a failure below that zone signaling momentum exhaustion rather than a thesis break.
• Use CAT as a multi-quarter AI infrastructure beneficiary: maintain long exposure on any retracement toward the mid-$800s, and consider selling out-of-the-money calls against the position into strength near $1,000 to monetize elevated implied volatility while preserving core upside.
• Hold DAL as a tactical reopening/premium-consumer long, but size modestly and keep risk tight; if it loses the mid-$70s support on volume, reduce exposure because the trade is most vulnerable to a renewed fuel shock or any softening in premium yields.
• Pair trade idea: long CAT / short a weaker industrial with less data-center exposure; the spread should favor CAT over the next 3-6 months if AI power demand continues to drive order growth and backlog conversion.
• Event-driven approach: on the next earnings cycle for all three, use any guide-up/gap-up to harvest some gains rather than chasing; the asymmetric move is likely to be in disappointment risk, not upside surprise, after such strong runs.