LGTO Legato Merger Corporation II

CUSIP No. 84445C 100

This Schedule 13D relates to shares of common stock, par value $0.0001 per share (“Common Stock”), of Southland Holdings, Inc., a Delaware corporation (the “Company”). The principal executive offices of the Company are located at 1100 Kubota Drive, Grapevine, Texas 76051.

(a) This Schedule 13D is filed by Walter Timothy “Tim” Winn. Mr. Winn is referred to herein as the “Reporting Person.”

(b) The business address of the Reporting Person is 1100 Kubota Drive, Grapevine, Texas 76051.

(c) The present principal occupation of the Reporting Person is serving as Co-Chief Operating Officer and Executive Vice President of the Company.

(d) The Reporting Person has not, during the last five years, been convicted in a criminal proceeding (excluding traffic violations or similar misdemeanors).

(e) The Reporting Person has not, during the last five years, been a party to a civil proceeding of a judicial or administrative body of competent jurisdiction and as a result of such proceeding was or is subject to a judgment, decree or final order enjoining further violations of, or prohibiting or mandating activities subject to, federal or state securities laws or finding any violation with respect to such laws.

(f) The Reporting Person is a United States citizen.

On May 25, 2022, the Company (known prior to the Closing Date (as defined below) as Legato Merger Corp. II (“Legato II”)) entered into an Agreement and Plan of Merger, dated as of May 25, 2022 (the “Merger Agreement”), by and among the Company, Southland Holdings LLC, a Texas limited liability company (“Southland”), and Legato Merger Sub, Inc., a Delaware corporation and a direct, wholly-owned subsidiary of Legato II (“Merger Sub”).

On February 14, 2023 (the “Closing Date”), as contemplated by the Merger Agreement, Merger Sub merged with and into Southland, with Southland surviving as a wholly-owned subsidiary of the Company, and with the former members of Southland (“Southland Members) becoming securityholders of the Company (the “Merger”). The Merger and other transactions contemplated by the Merger Agreement are referred to collectively herein as the “Business Combination”, and the consummation of the Business Combination on the Closing Date is referred to herein as the “Closing”.

Pursuant to the Merger Agreement, at the Effective Time (as defined below), by virtue of the Merger and without any further action on the part of the parties to the Merger Agreement, each membership interest in Southland (“Southland Membership Interest”) (expressed as a percentage) issued and outstanding immediately before the effective time of the Merger (the “Effective Time”) was converted into and became the right to receive, among other things, (I) a number of shares of Common Stock of the Company (the “Per Membership Interest Merger Consideration”) equal to (a) (i) $343,000,000 divided by (ii) $10.15, multiplied by (b) such Southland Member’s percentage of all Southland Membership Interests issued and outstanding immediately prior to the Effective Time (i.e., 100%), and (II) the right to receive a number of shares of Common Stock of the Company (the “Earnout Merger Consideration”) equal to (a) (i) $105,000,000 divided by (ii) $10.15, multiplied by (b) such Southland Member’s percentage of all Southland Membership Interests issued and outstanding immediately prior to the Effective Time, upon the achievement of certain Adjusted EBITDA targets set forth in the Merger Agreement.

At Closing, the Company issued 33,793,111 shares of Common Stock of the Company to the Southland Members in exchange for their Southland Membership Interests as Per Membership Interest Merger Consideration (such shares of Common Stock, the “Merger Consideration Common Shares”). As Southland Members, (i) the Reporting Person was issued 1,389,703 Merger Consideration Common Shares, (ii) the Walter Timothy Winn 2015 Irrevocable Trust was issued 1,520,690 Merger Consideration Common Shares, (iii) the Debra Nicole Winn Irrevocable 2020 Trust was issued 1,520,690 Merger Consideration Common Shares, and (iv) the Reporting Person’s spouse was issued 1,651,677 Merger Consideration Common Shares. The Reporting Person may be deemed to have shared voting and/or dispositive power over the shares of Common Stock of the Company held by (a) the Walter Timothy Winn 2015 Irrevocable Trust and the Debra Nicole Winn Irrevocable 2020 Trust as Trustee of each such trust and (b) the Reporting Person’s spouse. The description of the Merger Agreement contained in this Schedule 13D does not purport to be complete and is qualified in its entirety by the text of the Merger Agreement, which is filed as Exhibit 1 to this Schedule 13D and is incorporated by reference herein.

Additionally, on the Closing Date, certain stockholders of Legato II (the “Legato Insiders”) entered into a letter agreement (the “Letter Agreement) with certain Southland Members (the “Recipients”). Pursuant to the Letter Agreement, the Legato Insiders agreed that, upon consummation of the transactions contemplated by the Merger Agreement (the “Transactions”), they would transfer to the Recipients an aggregate of 765,544 shares of Common Stock of the Company. In consideration of the foregoing, the Recipients agreed, in both their capacities as members of Southland and as officers and/or managers of Southland, to use their best efforts to cause Southland to close the Transactions. As a Recipient, the Reporting Person received 137,798 shares of Common Stock of the Company. The description of the Letter Agreement contained in this Schedule 13D does not purport to be complete and is qualified in its entirety by the text of the Letter Agreement, which is filed as Exhibit 2 to this Schedule 13D and is incorporated by reference herein.

The securities covered by this Schedule 13D were acquired for investment purposes.

The Reporting Person currently serves as (i) a Class III Director of the Company and (ii) Co-Chief Operating Officer and Executive Vice President of the Company. As a director and officer of the Company, the Reporting Person may have influence over the corporate activities of the Company, including activities which may relate to the transactions described in clauses (a) through (j) of Item 4 of Schedule 13D.

Except as set forth in this Item 4, the Reporting Person does not have any present plans or proposals that relate to or that would result in any of the actions specified in clauses (a) through (j) of Item 4 of Schedule 13D. The Reporting Person retains the right to change his investment intent and may, from time to time, acquire additional shares of Common Stock or other securities of the Company, or sell or otherwise dispose of (or enter into plans or arrangements to sell or otherwise dispose of), all or part of the shares of Common Stock or other securities of the Company, if any, beneficially owned by the Reporting Person, in any manner permitted by law.

(a) – (b) The aggregate number and percentage of the outstanding shares of Common Stock of the Company beneficially owned by the Reporting Person are as follows:

(c) As disclosed in Item 3 of this Schedule 13D, pursuant to the terms of the Merger Agreement, at Closing, the Company issued 33,793,111 Merger Consideration Common Shares to the Southland Members in exchange for their Southland Membership Interests based on a price of $10.15 per shares. As Southland Members, (i) the Reporting Person was issued 1,389,703 Merger Consideration Common Shares, (ii) the Walter Timothy Winn 2015 Irrevocable Trust was issued 1,520,690 Merger Consideration Common Shares, (iii) the Debra Nicole Winn Irrevocable 2020 Trust was issued 1,520,690 Merger Consideration Common Shares, and (iv) the Reporting Person’s spouse was issued 1,651,677 Merger Consideration Common Shares. The Reporting Person may be deemed to have shared voting and/or dispositive power over the shares of Common Stock of the Company held by (a) the Walter Timothy Winn 2015 Irrevocable Trust and the Debra Nicole Winn Irrevocable 2020 Trust as Trustee of each such trust and (b) the Reporting Person’s spouse.

Also as disclosed in Item 3 of this Schedule 13D, pursuant to the terms of the Letter Agreement, as a Recipient, the Reporting Person received 137,798 shares of Common Stock of the Company. Auch shares were transferred by the Legato Insiders as consideration for the Recipients’ agreement, in both their capacities as members of Southland and as officers and/or managers of Southland, to use their best efforts to cause Southland to close the Transactions

(d) Members of the Reporting Person’s immediate family members may be deemed to have the right to receive or the power to direct the receipt of dividends from, or the proceeds from the sale of, the shares of Common Stock of the Company held by the Walter Timothy Winn 2015 Irrevocable Trust, the Debra Nicole Winn Irrevocable 2020 Trust and the Reporting Person’s spouse.

(e) Not applicable.

As disclosed in Item 3 of this Schedule 13D, on May 25, 2022, the Company (known prior to the Closing Date as Legato II) entered the Merger Agreement, by and among the Company, Southland, and Merger Sub. At Closing, the Company issued 33,793,111 Merger Consideration Common Shares to the Southland Members in exchange for their Southland Membership Interests based on a price of $10.15 per share. As Southland Members, (i) the Reporting Person was issued 1,389,703 Merger Consideration Common Shares, (ii) the Walter Timothy Winn 2015 Irrevocable Trust was issued 1,520,690 Merger Consideration Common Shares, (iii) the Debra Nicole Winn Irrevocable 2020 Trust was issued 1,520,690 Merger Consideration Common Shares, and (iv) the Reporting Person’s spouse was issued 1,651,677 Merger Consideration Common Shares. The Reporting Person may be deemed to have shared voting and/or dispositive power over the shares of Common Stock of the Company held by (a) the Walter Timothy Winn 2015 Irrevocable Trust and the Debra Nicole Winn Irrevocable 2020 Trust as Trustee of each such trust and (b) the Reporting Person’s spouse. Pursuant to the Merger Agreement, the Southland Members, including the Reporting Person, also have the right to receive the Earnout Merger Consideration upon the achievement of certain Adjusted EBITDA targets set forth in the Merger Agreement. The description of the Merger Agreement contained in this Schedule 13D does not purport to be complete and is qualified in its entirety by the text of the Merger Agreement, which is filed as Exhibit 1 to this Schedule 13D and is incorporated by reference herein.

Also as disclosed in Item 3 of this Schedule 13D, on the Closing Date, the Legato Insiders entered into the Letter Agreement with the Recipients. Pursuant to the Letter Agreement, the Legato Insiders agreed that, upon consummation of the Transactions, they would transfer to the Recipients an aggregate of 765,544 shares of Common Stock of the Company. In consideration of the foregoing, the Recipients agreed, in both their capacities as members of Southland and as officers and/or managers of Southland, to use their best efforts to cause Southland to close the Transactions. As a Recipient, the Reporting Person received 137,798 shares of Common Stock of the Company. The description of the Letter Agreement contained in this Schedule 13D does not purport to be complete and is qualified in its entirety by the text of the Letter Agreement, which is filed as Exhibit 2 to this Schedule 13D and is incorporated by reference herein.

Concurrently with the execution of the Merger Agreement, each of the Southland Members entered into an agreement (“Lock-Up Agreement”) not to transfer the Merger Consideration Common Shares received by such Southland Member pursuant to the Merger Agreement until six (6) months from the Closing, subject to certain exceptions. The Lock-Up Agreement shall not apply to any shares of Common Stock received by the Southland Members as Earnout Merger Consideration pursuant to the terms of the Merger Agreement. The description of the Lock-Up Agreement contained in this Schedule 13D does not purport to be complete and is qualified in its entirety by the text of the Lock-Up Agreement, the form of which is filed as Exhibit 3 to this Schedule 13D and is incorporated by reference herein.

In connection with the Business Combination, on the Closing Date, that certain Registration Rights Agreement, dated November 22, 2021, was amended and restated and the Company, certain Southland Members, the Company’s stockholders prior to its initial public offering (the “Initial Stockholders”), including each of Legato II’s officers and directors, and EarlyBirdCapital, Inc. (“EBC”) entered into an Amended and Restated Registration Rights Agreement (the “Amended and Restated Registration Rights Agreement”). Pursuant to the Amended and Restated Registration Rights Agreement, among other things, the Company will, within 45 days after the Closing Date, file a registration statement on Form S-1 to register for resale under the Securities Act the shares of Common Stock issued or issuable in connection with the Merger, the shares of Common Stock held by the Initial Stockholders or issuable upon the exercise of the Company’s warrants, each whole warrant to purchase one share of Common Stock for $11.50 per share (the “Warrants”), held by the Initial Stockholders (or their transferees) as of immediately after the Closing Date, and the shares of Common Stock and units issued to EBC (and its designees) in connection with the Company’s initial public offering. The material terms of the Amended and Restated Registration Rights Agreement are described in the definitive proxy statement/prospectus for the Business Combination, filed by Legato II on February 1, 2023 in the section entitled “Proposal No. 1 - The Business Combination Proposal - The Merger Agreement - Related Agreements”. The description of the Amended and Restated Registration Rights Agreement contained in this Schedule 13D does not purport to be complete and is qualified in its entirety by the text of the Amended and Restated Registration Rights Agreement, which is filed as Exhibit 4 to this Schedule 13D and is incorporated by reference herein.

SIGNATURES

After reasonable inquiry and to the best of my knowledge and belief, I certify that the information set forth in this statement is true, complete and correct.