Who will go all in on 2020? Here's how MLB teams are approaching a murky trade deadline

In customary times, blue skies and acres of baseball games, the trade deadline is a messy little creature, sotted with rash ambitions and boring regret, with cash considerations.

Some of it turns out fine. Or fine enough. Some not. Occasionally, it affords career headstone material, pending physicals.

The deadline is a complicated, frantic and spiritual exercise that is circus and ritual, mirage and holy day, cavalry charge and white flag.

In customary times.

This summer, the deadline is all that, the usual months-long ode to overanalysis and procrastination giving way to three hours of chaos, only ridiculously less certain.

Yay, 2020.

Like everything else that isn’t pet cats, jumbo bags of Oreos and Viking series on Netflix, the baseball season is not itself in the pandemic. For one, its next full slate of games will be the first since last month. For another, it’s gone about as well as anyone could have expected.

The season began July 23, nearly four months late. The trade deadline is Aug. 31, a month later than usual, and still about 75 games earlier than usual, and so in a typical season it would be asking general managers to make decisions on the authenticity of their teams — in relation to the other 29 — sometime in late April. Nobody would do that. It’s like choosing the perfect fitting jeans through the window of a clothing shop. From across the street. In the rain. While wearing no pants.

The Philadelphia Phillies, who haven’t seen October since 2011, who lost 13 of their first 22 games, whose relievers’ ERA was nearly 8, went aggressively into trade deadline season. On Friday evening, they acquired two right-handed relievers from Boston — Brandon Workman and Heath Hembree. Given splashy signings (Bryce Harper, Zack Wheeler, Didi Gregorius, Jake Arrieta) and trades (J.T. Realmuto) in recent winters, and an impatient fan base, aggressive ownership and a big payroll, the Phillies were predictably early out of the gate. Twenty-two games were plenty to determine they had the worst bullpen in the game.

Philadelphia Phillies' Bryce Harper, left, celebrates his home run with teammate J.T. Realmuto during the first inning of the first game of a baseball doubleheader against the Toronto Blue Jays, Thursday, Aug. 20, 2020, in Buffalo, N.Y. (AP Photo/Jeffrey T. Barnes)
Despite strong starts from recent splashy winter acquisitions Bryce Harper and J.T. Realmuto, the Phillies find themselves desperate for pitching help at the trade deadline. (AP Photo/Jeffrey T. Barnes)

It would be fair to expect similar enthusiasm from, say, the San Diego Padres (zero postseasons since 2006) and Cincinnati Reds (nothing since 2013), places where even a short and goofy season would be viewed with great affection. The New York Yankees are down about eight good players, but they’re also deep enough to make the playoffs anyway, then take their chances in whatever comes of that 16-team cat-fight. The hot prediction is that an 8-seed will beat a 1, because could you not see, say, Jacob deGrom outpitching Walker Buehler one night, Seth Lugo doing the same to Clayton Kershaw the next? It’s 2020. It’s baseball. It happens.

Similarly, in more than a few front offices, there are debates over what it is they’d be going all in for. To win a 60-game season that will be forgotten as soon as it’s over? To qualify for a best-of-three dice roll in the first of four playoff rounds? Do you trade away a decent prospect or two if there is a 5 percent chance the season is canceled in September? A 10 percent chance? And what if the virus rages through one of those October bubbles they’re talking about? You go home but your prospects stay in Detroit or Seattle or Boston or Pittsburgh or San Francisco?

Those predicting a quieter deadline, certainly as it relates to bigger-name (and higher-priced) players, ask how an organization that has furloughed and laid off dozens or hundreds of employees turns and spends millions of dollars on a fresh outfielder. Normally press-shy team owners have been eager to reveal the financial hit caused by fans-less baseball games, a development not guaranteed to end in 2021. The economic downturn — and the cover it provides — has agents predicting a soft winter for free agents, and low-ball offers might be difficult to defend in the wake of additional financial commitments made in August. Remember, they argued just a month ago they could barely pay the players they already had.

It’s not to say there aren’t trades to be had or that the deadline won’t be busy, if even on the margins. The Phillies are better already. About four teams, possible 10-game winning streaks notwithstanding, have managed to play themselves out of October. Everyone could use a starting pitcher or two, a reminder that — virus or no — some things in baseball do not ever change. If the Yankees, Atlanta Braves, New York Mets or Washington Nationals need to cover innings, if the St. Louis Cardinals, with still seven doubleheaders out there, need to cover innings, if the Cleveland Indians are going to continue without Mike Clevinger and Zach Plesac, then maybe Kevin Gausman (Giants), Taijuan Walker (Mariners), Alex Cobb (Orioles), Marco Gonzales (Mariners) or Dylan Bundy (Angels) is your man.

In an effort to cover themselves against a season that does not reach October, or comes apart early in October, there are likely to be a good number of contingency trades. That is, if a team acquires a player, the return is based on the season reaching its conclusion — player A if it does, player B if it does not.

In customary times, this is when you’d check the pending free agents. So, Trevor Bauer, Mike Minor, Jake Odorizzi, Masahiro Tanaka and James Paxton among starting pitchers, all on contenders in a season where nearly everyone is. Marcus Stroman, who opted out. Among position players, it plays the same. The Houston Astros wouldn’t trade outfielder George Springer. The Phillies wouldn’t trade catcher J.T. Realmuto. Marcus Semien, Marcell Ozuna and DJ LeMahieu are on good teams. Would the Red Sox trade their shortstop — Xander Bogaerts — in the middle of a rebuild, and would an owner commit to $100 million over the next five years for him?

So, perhaps, for the Indians or Marlins or Brewers or Nationals, teams that could use a bat (but, in the cases of the latter three, can’t be sure there’d be a universal designated hitter in ‘21), perhaps that’s Donovan Solano, perhaps Josh Bell, perhaps Andrelton Simmons.

So many perhaps-es. So many unknowns.

Is a 60-game season worth saving? At what price to win it, for two guaranteed games in October, when three or four weeks of baseball haven’t gone exactly as you might have projected? It all seems so uncertain. So messy.

That said, man, the Phillies really needed relievers. That 8 ERA was going on their headstone.

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