In the last two years, Orioles executive vice president/general manager Mike Elias has made two major trades leading up to the December deadline for offering contracts.

In December 2019, Elias dealt starting pitcher Dylan Bundy, who was two years away from free agency, to the Los Angeles Angels for four right-handed pitchers — Kyle Bradish, Kyle Brnovich, Isaac Mattson and Zach Peek.

Last year, he traded shortstop José Iglesias, whose 2021 option had been picked up just weeks before, to the Angels for two more right-handers Jean Pinto and Garrett Stallings.

Is it possible that Elias is planning another deal?

The Orioles have no players under major league contracts for 2022, and six eligible for arbitration — right-hander Jorge López, left-handers Paul Fry, John Means and Tanner Scott, first baseman/designated hitter Trey Mancini, and outfielder Anthony Santander.

According to The Athletic’s Ken Rosenthal, Major League Baseball and the Players’ Association have agreed to move up the deadline for offering contracts from December 2nd to November 30th. If the deadline remained December 2nd, that would have been the same day Major League Baseball could put a freeze on postseason transactions with a lockout if there isn’t a new contract to replace the expiring Collective Bargaining Agreement.

ESPN’s Buster Olney reported that Elias is gauging the market for Means, a starting pitcher who is estimated by MLBTradeRumors.com to be worth $3.1 million in his first season of arbitration eligibility.

Means and centerfielder Cedric Mullins are the two most attractive players the Orioles have. If the arbitration system remains intact in the new agreement, Mullins would be eligible for arbitration a year from now.

With three years of club control, Means is an attractive commodity — for the Orioles, who desperately need a top-shelf starter, and for other teams who could acquire three years of Means’ services.

Means, who was 6-9 with a 3.62 ERA, had a 4.0 WAR (Wins Above Replacement) in 2021, and pitched the Orioles’ first solo no-hitter since 1969 on May 5^th at Seattle.

Pitchers of his caliber with that much time before free agency rarely are available, and his possible departure could leave the Orioles painfully thin in the rotation.

While top pitching prospect Grayson Rodriguez should make his debut during the 2022 season, there isn’t a proven starter other than Means.

None of the other possible rotation candidates — Keegan Akin, Dean Kremer, Zac Lowther, Alexander Wells and Bruce Zimmermann — has had significant success in the major leagues, and the Orioles aren’t likely to spend on accomplished starring pitchers.

It would be interesting to see what sort of offers Elias could get for Means. There’s a prevailing theory in baseball that teams no longer trade their best prospects, With the Orioles needing so much help in the rotation, it would seem they’d have to get at least two top-notch starting rotation candidates plus additional prospects in return for Means.

A possible Means deal couldn’t be compared to the July 2018 deal made by Dan Duquette with the Los Angeles Dodgers for Manny Machado. The Orioles were under pressure to make a trade because Machado was an impending free agent.

The five players the Orioles got in return for Machado –Kremer, infielder Rylan Bannon, outfielder Yusniel Diaz, reliever Zach Pop, and infielder Breyvic Valera haven’t produced for the Orioles.

Even with Means, and the debuts of Rodriguez and top catching prospect Adley Rutschman in 2022, the Orioles aren’t expected to compete. If they trade Means, that could mean another season of 100-plus defeats and another No. 1 draft choice—unless the new Collective Bargaining Agreement includes a provision that prevents teams from drafting first in consecutive years.

Mullins, who has four years of club control left, might be even more valuable than Means.

It’s more likely that the Orioles will trade Mancini, who could make $7.9 million in arbitration, or Santander, whose 2022 salary could reach $3.7 million.

Mancini and Santander wouldn’t fetch the haul that Means could. A deal for Mancini so soon after he captured three American League Comeback Player of the Year awards could be politically risky for Elias.

Santander’s 2021 was a rough one. A year after being voted Most Valuable Oriole with an .890 OPS, Santander’s OPS dropped to .720, and injuries limited him to 110 games.

The Orioles would be trading low on Santander, whose defensive WAR dropped from .7 in 2020, a year in which he was a finalist for the Gold Glove in right field, to -.6 in 2021.

No Orioles: Mullins and first baseman Ryan Mountcastle were nominated for the All-MLB Team, but neither won. Mountcastle and Mullins will be introduced to the crowd at Sunday night’s Raven’s game against the Cleveland Browns.

Arena follow up: Last December, I wrote about the need for a new arena in Baltimore. On Wednesday, the city’s Board of Estimate is scheduled to vote on a deal to refurbish, but not replace, the Royal Farms Arena, built in 1962.

Brooklyn Nets star Kevin Durant’s venture capital company is partnering with Oak View Group, which built the UBS Arena in Elmont, New York, the new home of the NHL’s New York Islanders, which opened last Saturday.

The joint group will spend an estimated $150 million on the arena and increase seating capacity by about 10-to-15 percent. That could increase seating for basketball to about 14,000 and concerts to about 16,000.

The refurbishment could begin during the winter and be finished in 2023.