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TL;DR

  • Top News of the Week: C.H. Robinson agreed to pay $5.8B for a company that's expected to earn $137M this year. The only way that price makes sense is if Robinson can take $300M of cost out of RXO, and most of that comes from fewer people doing the work.

  • From Last Week’s News: ChatGPT will now show you wearing a jacket you found on someone else's website, and OpenAI is betting that's a better shopping play than the checkout feature it walked away from.

TOP NEWS OF THE WEEK

Coyote Shippers Are on Their Third Owner in 4 Years

C.H. Robinson is buying RXO for $5.8B in enterprise value. RXO shareholders get $17.25 in cash plus 0.0856 Robinson shares for each share they own. At Robinson's 16-day average price of $151.88, that works out to $30.25 a share, a 29% premium to Friday's close. Closing is expected in the first half of 2027, pending regulators and an RXO shareholder vote.

Combined, the company would have more than $25B in gross revenue, about 93K shippers and roughly 600K carriers, with truck brokerage at 73% of the mix.

RXO's consensus adjusted EBITDA for 2026 is $137M, and Robinson is paying more than 42x that. The $300M in savings Robinson is promising is more than double what RXO earns on its own, so most of what Robinson is paying for is its own cost plan. The deck gets to a 13.2x multiple by counting the full $300M, which Robinson expects to reach within two years of closing.

Robinson says it has already done this to itself, and all of the evidence it offers is self-reported. By its count, enterprise productivity is up more than 60% since the end of 2022, adjusted operating margin grew 490 basis points last year and more than 100 AI agents now handle quote-to-cash work. Its own chart puts adjusted gross profit per employee at $214K company-wide in 2025 and $331K in the North American surface unit, compared with $164K at RXO.

About 80% of the savings is supposed to come from cost-to-serve and shared services, which means fewer people moving the same loads while software takes over work RXO staff do now. Real estate, insurance, and moving RXO onto Robinson's vendor contracts account for the remaining 20%. CFO Damon Lee said Navisphere will become the system of record where the truckload and LTL businesses overlap.

RXO matters more to retail than the brokerage numbers suggest. Retail and ecommerce customers made up 37% of its 2025 revenue, and its last-mile unit handles more than 11 million deliveries a year, much of it heavy goods with in-home assembly. RXO spun out of XPO in 2022 and bought Coyote Logistics from UPS in 2024, so a shipper who started with Coyote would be on its third owner in about four years. Lee called RXO's expedited and last-mile technology "very interesting" and potentially complementary but didn't describe any plans for it.

Robinson expects net leverage of 2.9x at close and is targeting 1.75x to 2.25x by the end of 2028, with buybacks paused until then. The deck says the deal doesn't depend on a freight market recovery, which holds only if the savings arrive on schedule, since without them Robinson is carrying that debt against a business earning $137M a year. The company has $4.5B in committed financing, including a bridge facility from Morgan Stanley.

THE BIG IDEA

Orbis, RXO's largest shareholder, supports the deal, and MFN Partners has agreed to vote its roughly 17% stake in favor. Both are backing a price where most of the value depends on how much RXO work Robinson can move to software. Neither the release nor the deck says how many RXO jobs that involve.

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The Truth About Last Week: ChatGPT Can Now Put the Jacket On You

OpenAI is having another go at shopping inside ChatGPT, and this time it's starting further up the funnel. It launched two features globally on Thursday.

  • You can upload a selfie or full-body photo and tap Try On in the shopping results to see the jacket on yourself, or send a screenshot of an item from any site.

  • A new Favorites feature saves products you like to a Library in the app alongside your try-on images.

  • You can also upload a photo of a celebrity's outfit and ask ChatGPT to find the pieces that are for sale.

Instant Checkout came first, and it didn't perform well, so OpenAI changed course. The company has moved from closing the sale to inspiring it, and that puts ChatGPT up against Pinterest and Google, which have dominated fashion discovery in recent years. Google launched its own virtual try-on in July 2025, so I don't think OpenAI is early to this.

OpenAI says the new ChatGPT Images 2.5 model produces more natural lighting and richer textures, though that's its own assessment. The coverage I've seen has no numbers on conversion or returns, and returns are what apparel retailers will be watching.

WHY IT MATTERS

If ChatGPT sparks the purchase and the retailer's own site closes it, who gets credit for that sale, and what will OpenAI eventually want to charge for it?

Watson In The Wild