Why a losing baseball team gets bolder as the trade deadline nears

Sports 5 min 80 sources

With MLB's August 3 deadline six weeks out, the standings are forcing teams to pick a side — sell, buy, or hold — and a team's record, not its talent, decides which.

Key takeaways

MLB's August 3 trade deadline is sorting teams into buyers and sellers — and a team's record this year, not its roster, decides which: the losing Giants are shopping their stars while teams barely ahead play it safe.
Fox is buying the streaming platform Roku for about $22 billion to own the ad-supported TV screen, the same bet behind its estimated $250 million in World Cup hydration-break ad sales.
The money keeps climbing across sport — a projected $260 million for Lamar Jackson, €60 million for Cucurella, Utah's first college private-equity deal, and the title-winning Knicks now valued near $10 billion.

Baseball’s trade deadline is still six weeks away — August 3 — but the standings are already deciding who plays it safe and who gambles. [22] A team’s record, more than its roster, is sorting the league into buyers and sellers. And the teams in the most interesting spots are the ones whose record this year doesn’t match the plan they started with.

The Giants are losing, so they’re getting bold

The San Francisco Giants are 29-43, sixteen games behind the Los Angeles Dodgers in their division and out of realistic contention. [34] So they’re doing the thing a losing team does: opening up. They’ve “put out feelers” on their three highest-paid hitters — Rafael Devers, Willy Adames, and Matt Chapman — plus other veterans, according to ESPN’s Buster Olney. [34] A year ago the Giants made the season’s most shocking deal to win, acquiring Devers from Boston as a final piece. It didn’t work. Now they’re open to selling him.

One name they won’t move: ace pitcher Logan Webb. The Giants have “zero plans” to part with him, one source told The Athletic’s Ken Rosenthal. [40] That’s the line a selling team draws — sell the parts that don’t define your future, keep the one that does.

The Astros are barely behind, so they’re cautious

The Houston Astros are seven games under .500 at 32-39 — but only three games out of a playoff spot, because the American League is weak this year. [22] That’s a different kind of position, and it produces a different kind of move. With few top prospects to trade, Houston can’t go big; reports say star hitter Yordan Alvarez “isn’t going anywhere.” [22] A team this close to the line doesn’t gamble its future or surrender. It waits, adds on the margins, and trusts what it has.

The St. Louis Cardinals show the flip side. They started the year rebuilding and traded veterans away, expecting to sell this summer. [22] Instead they’re playing well and sit in a wild-card spot, five games back. The plan said sell; the standings say maybe don’t. A team ahead of where it expected to be gets to do nothing — and nothing, here, is a choice.

The same logic, one position over

The deadline runs on this. The Miami Marlins are again fielding interest in ace Sandy Alcántara, who’s under team control for one more year at a $21 million club option. [20] Pitching is the deadline’s scarcest currency — every contender needs arms, and there are never enough — so a non-contending team holding a good one holds leverage. [20] The New York Yankees, at 43-27 and looking at a soft AL, are expected to buy precisely because they’re ahead and the door is open. [15] The Atlanta Braves, leading their division, are eyeing which underperformer to move, not which star to chase — a team ahead trims, it doesn’t reach. [17]

Even a struggling star reads through this lens. The San Diego Padres are 35-33 and clinging to a wild-card spot, but Manny Machado’s bat has cratered, and ESPN now frames it as a lasting concern, not a slump. [79] For a team on the line, one underperforming contract is the difference between buying and standing still.

The game on the field is shifting, too

Off the trade board, the sport itself is changing shape. Six of the eight position players for the first-place Cleveland Guardians one day last week were 5’11” or shorter. [63] Rule changes — no defensive shifts, limits on pickoffs, a runner placed at second base in extra innings — have rewarded contact, speed, and small ball over the all-or-nothing power game. Bunt attempts are up 25% from last year and 44% from three years ago, and qualified hitters under six feet have jumped 87% since 2008. [63] The Cardinals, Guardians, and Braves lead the league in short players — and all three are winning. [63] When the rules pay differently, teams play differently.

Around the business of sport this week

Fox bets $22 billion on free TV. Fox agreed to buy the streaming platform Roku — its name on more than 100 million devices — in a deal valued at about $22 billion including debt, making Fox the third-largest player in US television by share of viewing. [7] [13] The logic: viewers are shifting from paid subscriptions to cheaper, ad-supported streaming, and Fox wants to own the screen the ads run on. [7] The payoff is already visible — Fox is estimated to make around $250 million on World Cup commercials during the tournament’s hydration breaks alone, more than half what it paid for the broadcast rights. [44]

The quarterback salary leapfrog continues. Two days after the Kansas City Chiefs handed Patrick Mahomes a half-billion-dollar extension, Baltimore’s Lamar Jackson is reportedly next in line — ESPN’s Bill Barnwell projects roughly four years and $260 million, about $65 million a year, which would make Jackson the highest-paid player in NFL history. [6] Each record contract resets the market for the next quarterback, who then sets a new one.

The transfer window opens with money moving. Real Madrid agreed to sign defender Marc Cucurella from Chelsea for €60 million (about £52m), even though he signed a new Chelsea deal only last summer. [23] Tottenham — twice 17th in the Premier League and barely safe — agreed a £52 million fee for Brighton’s Jan Paul van Hecke, a club that finished near the bottom spending big to climb. [12] [43]

College sports takes its first private-equity check. Utah finalized a deal with the investment group Otro Capital, becoming the first US athletic department to partner with private equity, and set up a new company, Crimson Brand Partners, to run its ticketing, branding, and sponsorships. [35] Terms weren’t disclosed; officials described a “nine-figure impact.” The cash comes now; the investor’s return comes from the commercial slice of Utah sports they now hold.

The cost of winning shows up on the books. The Oklahoma City Thunder, built cheaply around young talent, are about to cross into the NBA’s harshest payroll territory as new extensions for Chet Holmgren and Jalen Williams take effect. [78] And the New York Knicks, who just won the title, are now worth $9.75 billion by Forbes’ estimate — up from $334 million when James Dolan took over Madison Square Garden in 1999. [64] Winning is expensive; being worth winning is worth billions.

02 · Lesson · why it matters

The right amount of risk depends on whether you're winning

How bold to be isn't a personality. It's a reading of where you stand — and the team that's behind should get bolder, not safer.

A losing team does the strange thing

The San Francisco Giants are sixteen games out of first place. So they’re putting their best hitters on the market — Devers, Adames, Chapman, the most expensive bats they own. To a fan, that can look like surrender. It’s the opposite. It’s the rational move of a team that has read its position correctly and decided to gamble on the future instead of clinging to a present that isn’t working.

Now look at the Houston Astros. Below .500, like the Giants — but only three games out of a playoff spot, because the league around them is weak. Houston is doing almost nothing. No big sell-off, no blockbuster buy. Standing still.

Two losing records. Two opposite moves. The difference isn’t talent or nerve. It’s distance from the line.

Risk is not a trait. It’s a function of position.

We talk about risk like it’s a character setting — some people are bold, some are cautious. In a contest, that framing is wrong. The correct amount of risk to take is not fixed. It bends with where you stand in the game.

When you are behind and time is short, safe play locks in the loss. The only paths that lead anywhere good run through some danger, so you take the danger. When you are ahead, the reverse holds: a bold move can only cost you the lead you already have, so you protect it and let the clock work for you.

This is why a football team trailing late pulls its goalkeeper for an extra attacker, or goes for it on fourth down instead of punting. It’s why a team that’s ahead runs the ball, stays in bounds, and bleeds the seconds. Neither is brave or timid. Each is the right reading of a different position.

The Giants are bold because they have to be

The Giants tried the safe-looking thing first. A year ago they made a win-now trade for Devers, the supposed final piece. It didn’t work, and the standings have closed the door for this season. Holding those players now — playing it safe, hoping — would cost them the one thing a losing team can still win: the future. Prospects, payroll room, a fresh start.

So they sell. The bold move. And notice the one player they won’t trade: their ace, Logan Webb. Even a gambling team doesn’t gamble everything. Webb is the part of the future you keep. The position tells you not just how much risk to take, but where.

The Cardinals show the mirror image. They planned to sell — they’re rebuilding — but they’ve played better than expected and climbed into a playoff spot. Now the safe move, doing nothing, is the smart one. They got ahead of their own plan, so they stopped taking risk. The plan didn’t change them. Their position did.

The error is reading your position wrong

Here’s where it goes wrong, on the field and off it. The dangerous mistake isn’t being bold or being cautious. It’s mismatching the two to your situation — playing safe when you’re behind, or gambling when you’re already ahead.

The team that’s losing and keeps playing it safe — protecting a lead it doesn’t have, waiting for a comeback that needs action it won’t take — runs out of clock. And the team that’s comfortably ahead and reaches for the spectacular play it didn’t need is the one that hands the game back. Both are reading the scoreboard wrong. Both are taking the right amount of risk for a position they’re not actually in.

The Padres sit right on that line — barely above .500, clinging to a wild-card spot — and one cratering contract, Manny Machado’s bat, is the difference between buying and standing still. On the line, the reading gets hardest, because the safe move and the bold move are almost the same size, and a single piece can tip which one is correct.

What the scoreboard is really telling you

So the next time a team behind makes a move that looks reckless, or a team ahead makes one that looks dull, look at the standings before you judge it. The boldness isn’t the point. The fit between the boldness and the position is.

And the harder thing underneath: you rarely get to choose your boldness freely. The game chooses it for you. Where you stand decides how much risk is correct, and the same move — pulling the goalie, selling the star, sitting still — is wisdom in one position and folly in another. Reading the position is most of the skill. It’s also the part no scoreboard reads for you. You’re inside the game, holding an incomplete picture of exactly where you stand — and that, more than nerve, is what makes the call hard.

03 · Lab · your turn

Play Safe or Gamble

Set your team's standing, choose a move, and feel how the right amount of risk flips depending on whether you're behind or ahead.

04 · Hope · carry this

Being behind is not the same as being beaten. The season teaches what every losing team relearns each summer — that a bad position is still a position, and the next right move is always there to be read.